United States v. Jeffrey Howard

Case: 13-40767 Document: 00512762524 Page: 1 Date Filed: 09/09/2014

IN THE UNITED STATES COURT OF APPEALS
FOR THE FIFTH CIRCUIT United States Court of Appeals
Fifth Circuit

FILED
September 9, 2014
No. 13-40767 Lyle W. Cayce
Clerk

UNITED STATES OF AMERICA,

Plaintiff–Appellee
v.

JEFFREY TODD HOWARD,
Defendant–Appellant

Appeal from the United States District Court
for the Southern District of Texas

Before HIGGINBOTHAM, JONES, and PRADO, Circuit Judges.
EDWARD C. PRADO, Circuit Judge:
This appeal from a bench trial verdict raises a difficult question
concerning the criminal law of attempt. The government caught the
Defendant–Appellant Jeffrey Howard (“Howard”) in a sting operation. A
government agent impersonated a mother offering up her two minor daughters
for sex. Howard sent the agent sexually explicit photographs and asked that
she show the photographs to the girls. He also suggested that the agent
procure birth control for and perform sex acts on her daughters to get them
ready for him. But Howard did not make travel arrangements to Corpus
Christi, Texas—where the fictional mother and her two daughters lived.
Further, the government agent tried to get Howard to commit to book a flight—
instructing Howard to “take it or leave it,” and Howard responded “okay, I’ll
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No. 13-40767
leave it.” Three months, later the police arrested Howard in California.
Howard was convicted by bench trial of attempt to knowingly persuade, induce,
entice, or coerce a minor to engage in illegal sexual activity in violation of 18
U.S.C. § 2422(b). 1 He appeals challenging the sufficiency of the evidence and
the constitutionality of the statute.
The principal question in this appeal is whether Howard’s conduct
crossed the line from “preparation” to “attempt” to knowingly persuade, induce,
entice, or coerce a minor to engage in illegal sexual activity. We address this
question, and Howard’s constitutional arguments, in turn below, informed by
the applicable law and the record in this case.
I. BACKGROUND
Because this appeal involves a challenge to the sufficiency of the
government’s proof, we summarize the facts below in the light most favorable
to the bench trial finding of guilt, consistent with the record. See United States
v. Morgan, 311 F.3d 611, 613 (5th Cir. 2002). The evidence supporting
Howard’s conviction was gathered through a three-week sting operation in
which Detective Alicia Escobar of the Corpus Christi Police Department posed
as the mother of two fictitious underage girls from February through March
2012. During this time period, Howard was unemployed and living with his
girlfriend in California. As a result of a basketball injury to his back, Howard

118 U.S.C. § 2422(b) provides:
Whoever, using the mail or any facility or means of interstate or foreign
commerce, or within the special maritime and territorial jurisdiction of the
United States knowingly persuades, induces, entices, or coerces any individual
who has not attained the age of 18 years, to engage in prostitution or any
sexual activity for which any person can be charged with a criminal offense, or
attempts to do so, shall be fined under this title and imprisoned not less than
10 years or for life.
In this case, the sexual activity that Howard could have been charged with was sexual
assault under the Texas Penal Code § 22.011.
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was bedridden. Detective Escobar, posing as the fictitious mother, “Melinda
Posada,” was introduced to Howard through Iris Cabrielez.
A. The Criminal Investigation
The criminal investigation of Howard started after he corresponded with
Iris Cabrielez. What began as small talk on a social-networking website
escalated into a flirtation and finally took a turn when Howard brought up
“taboo” and asked Cabrielez, “can you get me a quince?” 2 Cabrielez took this
to mean that Howard was asking for a fifteen-year-old girl for sex. Cabrielez
said no and explained: “I would never put a person lol in that position.”
Howard replied: “Okay. Well it’s worth 5k a piece, but okay.” Howard asked
Cabrielez to “[f]ind me one. Do you have a daughter?” When Cabrielez said,
“no,” Howard pressed on: “Does any of your home girls?” Cabrielez replied: “I
was raped at 13. I would never put a kid in that position. . . . I have a 15-year-
old niece who I can’t stand lol but never put her in a position like that.” To
which Howard replied, “send me a pic” and then said, “I want to see your niece
babe.” Cabrielez took a screen shot of the conversation on her phone and went
to the authorities.
Cabrielez contacted Detective Alicia Escobar. Detective Escobar works
with the Corpus Christi Police Department’s Internet Crimes Against Children
Task Force. Detective Escobar created a fictitious persona, Melinda Posada,
complete with an email address, instant-message account, and Facebook
profile. Cabrielez introduced Howard to Melinda Posada as her friend with
access to children.
The next day, Howard sent an email to Detective Escobar’s fictitious
persona’s email address. 3 Detective Escobar replied: “[Cabrielez] mentioned

2Quince means “fifteen” in Spanish.
3For convenience, we refer to Detective Escobar here even though she was posing as
Melinda Posada.
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taboo. Can you tell me more?” Howard responded: “I’m sorry over the phone
would be better, not over email.” Howard sent her his phone number, and they
made a plan to talk the next day. 4
Howard called Detective Escobar. On the call, Detective Escobar asked
Howard: “What are you looking for? [Cabrielez] told me . . . that you wanted
her to get you a 15-year old. I said, I don’t know if I can help because my
daughter is 14 . . . and I have an 11-year-old daughter.” Howard confirmed
that he was interested in having sex with children, and that he was interested
in having sex with Detective Escobar’s 14-year-old. He also explained that he
did not want to wear a condom to have sex with her daughters, and that he
was “disease free and he had paperwork to provide” to Detective Escobar,
though he never sent any such paperwork. He also said that “he would
definitely travel to Corpus Christi to have sex with [Detective Escobar’s]
daughter.”
Howard asked for photographs of Detective Escobar’s daughter and
offered to and ultimately did send a picture of his penis. Detective Escobar
testified at trial that, based on her training and experience, she thought that
Howard sent the picture “[t]o confirm that he was not a cop, as well as to
convince me to send a picture . . . to make sure that [the daughters] were real
and I was who I was saying I was.”
The trial court admitted audio recordings and transcripts of telephone
and electronic-messaging conversations between Howard and Detective
Escobar containing explicit sexual talk. In the conversations, Howard
described with specificity and detail the sex acts he intended to perform with
the underage girls and their mother. He often masturbated during these

4 Detective Escobar testified that, in her experience, suspects “automatically prefer to
talk on the phone because they don’t want evidence, and they don’t want anything to be able
to be recovered.”
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conversations. At one point, Detective Escobar accused Howard of being “all
talk,” and he replied: “I’m not.”
In one conversation, Detective Escobar asked Howard: “What do you
want me to do to get them [the girls] ready?” He asked her to perform oral sex
on the girls. “I ain’t going to do that,” she said. “That’s your job lol. Maybe I’ll
look up someone down here so they can get ‘em started,” Detective Escobar
said. “No. I want to be first,” Howard replied. “Just get a dildo,” he proposed.
Detective Escobar testified that “people who are sexually interested in
children . . . have particular ideas as far as getting the children ready.” She
called this behavior “grooming”: “[T]hey want you to do different things to your
children in order to make them ready, especially if they never have had sex
before.”
In telephone conversations and over email, Howard also discussed the
girls’ birth control with Detective Escobar. After Detective Escobar told him
that her fourteen-year-old daughter had been prescribed birth control, Howard
asked, “Did she get the shot? The shot’s better.”
Detective Escobar also spoke with Howard about possible travel plans.
Howard asked Detective Escobar “How far are you from El Paso?” At this point
in the investigation, Detective Escobar believed that Howard “was in El Paso
or near El Paso . . . and he was actually trying to see how far it would take him
to drive.” After Detective Escobar told Howard that the drive was about ten
hours, Howard replied: “Damn. That far lol. Yes. Wish I could come to Corpus.
I’m really ex[c]ited about how my girls doing.” Howard asked whether
Detective Escobar had shown the girls the picture of his penis; she said yes and
that “the girls were now curious about having sex with him.” Howard
responded: “that’s awesome. I can’t wait for all three of us to be cool and be
like a happy family.” Howard explained that he had not checked flights yet,
but said “I will, though. This is going to be awesome . . . am I dreaming lol???”
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Howard said “he would definitely travel to Corpus Christi to have sex with
[Detective Escobar’s] daughter,” asked what airport he should fly into,
mentioned he could fly Southwest Airlines, and inquired about specific hotels.
Detective Escobar pressed Howard to get him to commit to traveling to
Corpus Christi: “Hey . . . what does your schedule look [like] for next month?
Can you squeeze us in? I think the girls are nervous and anxious,” Detective
Escobar said. Howard replied: “Okay. I will look up some flights, idk [(short
for ‘I don’t know’)]. I’m so busy these next few months, but I’ll see what’s up.”
Detective Escobar testified that Howard never, to her knowledge, rented a car,
booked a flight, purchased a bus ticket, made a hotel reservation, or gave any
other indication that he was going to travel on a certain date and time to meet
with Detective Escobar’s children. Detective Escobar sent him the phone
numbers for three hotels and told him the closest airport is Corpus Christi
International Airport.
In the last telephone conversation in March 2012, Howard demanded
that Detective Escobar send him photographs or put one of her daughters on
the phone: “Put Brit on 3-way,” he demanded, in the midst of a graphic, highly
sexual conversation. Detective Escobar refused: “No convos til you’re here. I
don’t want to scare her. I want this to be a good thing for her. I want her to
feel it before she hears you.” Howard replied: “Well, honestly, I want to make
sure I am not coming for nothing. . . . [I am] [p]robably walking into a trap.”
Later, Howard asked: “why do I have to book a flight to talk to the girls? That
doesn’t make sense. What difference does it make?”
At this point, Detective Escobar testified that she drew a “line in the
sand”: “You ain’t talking to the girls. I told you that that I ain’t getting their
hopes up and introducing when you ain’t even here. Take it or leave it.”
Howard responded: “Okay. I’ll leave it. You don’t talk to me like that. Nobody
does.” This message was the last time Howard contacted Detective Escobar.
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Three months later, the police arrested Howard in Northridge,
California.
B. The Bench Trial
Howard waived his right to a jury trial and proceeded to bench trial
before the district judge. At the close of the government’s case in chief, Howard
through counsel moved for a directed verdict. Howard argued the government
did not prove that Howard took a “substantial step” because his conduct
amounted to mere preparation. The district court orally rejected Howard’s
motion for a directed verdict and explained: “Sending a picture of his penis to
[an] undercover officer and asking her to show it to minors, it would be hard to
overlook that as a substantial step.” The district court apparently was
persuaded by the Eleventh Circuit’s decision in United States v. Lee, 603 F.3d
904 (11th Cir. 2010).
The district court found Howard guilty and sentenced him to 120-months
imprisonment, the mandatory-minimum sentence. Howard timely appeals.
II. JURISDICTION AND STANDARD OF REVIEW
The district court had jurisdiction under 18 U.S.C. § 3231, and this Court
has jurisdiction under 28 U.S.C. § 1291 to review the district court’s final
judgment. We review a district court’s finding of guilt after a bench trial “to
determine whether it is supported by any substantial evidence.” United States
v. Allen, 587 F.3d 246, 256 (5th Cir. 2009) (per curiam) (quoting United States
v. Serna–Villarreal, 352 F.3d 225, 234 (5th Cir. 2003)) (internal quotation
marks omitted). “[E]vidence is sufficient to sustain a conviction if any rational
trier of fact could have found that the evidence established guilt beyond a
reasonable doubt. This court examines the evidence as a whole and construes
it in the light most favorable to the verdict.” Id. (alteration omitted) (quoting
Serna–Villarreal, 352 F.3d at 234) (internal quotation marks omitted).

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We review preserved challenges to the constitutionality of a criminal
statute de novo. United States v. Clark, 582 F.3d 607, 612 (5th Cir. 2009). But
if the constitutional challenge was not presented to the district court, we
review for plain error. United States v. Knowles, 29 F.3d 947, 950 (5th Cir.
1994). Plain error exists if “(1) there is an error, (2) the error is plain, (3) the
error affects substantial rights[,] and (4) the error seriously affects the fairness,
integrity or public reputation of judicial proceedings.” United States v. Garcia–
Carrillo, 749 F.3d 376, 378 (5th Cir. 2014) (per curiam) (alterations and
internal quotation marks omitted).
III. DISCUSSION
Howard seeks reversal of his criminal conviction on two grounds. First,
Howard argues there was insufficient evidence to support his conviction for
violation of § 2422(b) because he did not take a substantial step toward enticing
a minor to have illegal sex. Second, Howard contends the “attempt” provision
of § 2422(b) is unconstitutionally vague and overbroad because it criminalizes
free speech. We address each argument in turn.
A. Howard’s Challenge to the Sufficiency of the Evidence
Federal courts, including the Fifth Circuit, apply the Model Penal Code’s
“substantial step” test to determine whether a defendant’s conduct manifests
attempt to commit a crime. See, e.g., United States v. Hernandez–Galvan, 632
F.3d 192, 198 (5th Cir. 2011) (“[T]he ‘substantial step’ test from the Model
Penal Code . . . is now the majority view among the states and federal courts,
including the Fifth Circuit.”). This test has two elements: (1) the specific intent
to commit the underlying crime, mens rea, and (2) conduct which constitutes a
“substantial step” toward the commission of the crime, actus reus. United
States v. Barlow, 568 F.3d 215, 219 (5th Cir. 2009). This “‘substantial step’
approach asks whether a person ‘purposely does or omits to do anything that,
under the circumstances as he believes them to be, is an act or omission
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constituting a substantial step in a course of conduct planned to culminate in
his commission of the crime.’” Hernandez–Galvan, 632 F.3d at 198 (quoting
Model Penal Code § 5.01(1)(c)).
The “substantial step” must be conduct that strongly corroborates the
firmness of the defendant’s criminal intent. Id. Acts which are merely
preparatory are not enough. United States v. Mandujano, 499 F.2d 370, 377
(5th Cir. 1974). A “substantial step” is “more than mere preparation,” but is
“less than the last act necessary before” the crime is in fact committed. United
States v. Manley, 632 F.2d 978, 987–88 (2d Cir. 1980). This requirement
“prevents the conviction of persons engaged in innocent acts on the basis of a
mens rea proved through speculative inferences, unreliable forms of testimony,
and past criminal conduct.” United States v. Oviedo, 525 F.2d 881, 884–85 (5th
Cir. 1976). 5
To determine whether Howard’s conduct crossed the line between
preparation and attempt, we must first clearly define the conduct that
§ 2422(b) criminalizes. In Barlow and Broussard, we clarified that § 2422(b)
“does not require that the sexual contact occur, but that the defendant sought
to persuade the minor to engage in that contact.” United States v. Broussard,
669 F.3d 537, 548 (5th Cir. 2012) (quoting Barlow, 568 F.3d at 219 n.10)
(internal quotation marks omitted). Put another way, as the First Circuit
observed, “[§] 2422(b) criminalizes an intentional attempt to achieve a mental
state—a minor’s assent—regardless of the accused’s intentions vis-à-vis the
actual consummation of sexual activities with the minor.” United States v.
Dwinnells, 508 F.3d 63, 71 (1st Cir. 2007); see also United States v. Bailey, 228
F.3d 637, 639 (6th Cir. 2000) (“Congress has made a clear choice [in 18 U.S.C.

5 See also Hernandez–Galvan, 632 F.3d at 200 (“[T]o the extent the ‘substantial step’
test requires an act that provides strong evidence of the actor’s mental state, it might not
criminalize some slight acts that go beyond mere preparation.”).
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§ 2422(b)] to criminalize persuasion and the attempt to persuade, not the
performance of the sexual acts themselves.”).
Howard argues that his actions—talking to an undercover police officer
for less than a month without making flight or hotel reservations or agreeing
on a specific date to meet in Corpus Christi—“can best be described as mere
preparation.” Howard relies on the Seventh Circuit’s decision in United States
v. Gladish, 536 F.3d 646, 649 (7th Cir. 2008) to support his view that a
substantial step for purposes of § 2422(b) at least requires “setting up a definite
meeting time and place, purchasing tickets or making hotel reservations, [or]
driving to the proposed meeting place.”
The government argues that Howard took a substantial step and points
to the following evidence. Howard first corresponded with Detective Escobar
after he offered “Cabrielez $5,000 if she could find children for sex.” Howard
sent Detective Escobar sexually explicit images of himself and instructed her
to share them with “Brianna” and “Britany.” He asked whether Detective
Escobar “had shown the picture . . . to the girls and wanted to know their
reaction.” He directed Detective Escobar to obtain birth control for the girls,
repeatedly demanded pictures of the girls, and instructed Detective Escobar to
perform sex acts on the girls “to prepare them for him.” The government relies
on the Eleventh Circuit’s decision in United States v. Lee, 603 F.3d 904, 915
(11th Cir. 2010) for the proposition that “[f]irm plans to travel” are not required
if the defendant “took other steps sufficient to achieve the end that is the object
of the attempt.’” Lee, 603 F.3d at 915.
1. Fifth Circuit Case Law
Prosecutions under 18 U.S.C. § 2422(b) ordinarily are the result of sting
operations. The defendant discusses a specific meeting place with an
undercover police officer posing as a minor (or a minor’s parent). The

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defendant shows up at the meeting place and is arrested. 6 We have had no
trouble affirming these convictions finding that, by traveling to the meeting
place, the defendant took a substantial step toward the commission of the
crime strongly corroborative of intent. See, e.g., Barlow, 568 F.3d at 219–20.
For example, in Barlow we affirmed a conviction where the defendant agreed
to meet the minor in a state park and “loaded his foster sons into the car with
him and drove to the state park and waited for [the minor girl’s] arrival,” even
though he left when he saw an FBI agent. Id. at 219. We explained that the
defendant’s “early departure does not undo the substantial steps he had
already taken.” Id. at 219–20. 7
Travel to a meeting place is, therefore, sufficient to establish attempt.
But we have never held that travel or plans to travel are necessary. See
Broussard, 669 F.3d at 550 (“Broussard never traveled or made definitive plans
to travel to meet TL and KH, but . . . we have never ruled that physical

6 See, e.g., United States v. Caudill, 709 F.3d 444, 445 (5th Cir.), cert. denied, 133 S.
Ct. 2871 (2013) (affirming conviction where defendant’s “online conversation culminated in
an arrangement that Caudill would pay one hundred dollars in exchange for the officer
providing the two girls, who would then perform sexual acts with Caudill. That evening,
Caudill drove to the designated hotel but left when the officer failed to respond to text
messages. Caudill was arrested shortly thereafter, and the police found condoms, a $100 bill,
and diapers in his vehicle.”); United States v. Farner, 251 F.3d 510, 511 (5th Cir. 2001)
(affirming conviction where the defendant “confessed that he had traveled to Houston to meet
Cindy [an FBI agent who represented herself as a 14-year-old girl]. He claimed that he had
no specific plans with Cindy, but he would have done anything she wanted to do. He further
admitted that he had planned to take her into his hotel room, and that he had discussed sex
with her prior to traveling to Houston. A search of his hotel room revealed a box of condoms
and a tube of surgilube lubricant.”).
7 Howard did not communicate with a minor. Indeed, “Britany” and “Brianna” never

existed. Further, Howard communicated through an adult intermediary, Detective Escobar,
who posed as the girls’ mother. But that does not matter. The Fifth Circuit has held the
nonexistence of the minor and communication through an adult intermediary are not viable
defenses to criminal liability under § 2422(b). Caudill, 709 F.3d at 447 (“We join our sister
circuits in holding that a defendant who communicates solely with an adult intermediary can
be held to violate § 2422(b).”); Farner, 251 F.3d at 512–13 (rejecting the defendant’s argument
that “it was legally impossible for him to have committed the crime since the ‘minor’ involved
in this case was actually an adult.”).
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proximity or travel or plans to travel is necessary to constitute a substantial
step under § 2422(b).”). In Broussard, we explained that the Fifth Circuit has
“never addressed whether obtaining a phone number and having conversations
with a minor about meeting for illicit sexual activity constitutes a substantial
step toward persuading a minor to engage in illicit sexual activity under
§ 2422(b)—nor has any intervening decision clarified the issue.” Id. On plain
error review, we concluded that, therefore, “any error on the district court’s
part in accepting Broussard’s plea on the factual basis established by the
evidence could not be plain.” Id.
This appeal presents the issue that we left open in Broussard. What
conduct—in the absence of travel or definite plans to travel—crosses the line
from mere preparation to attempt to violate § 2422(b)?
2. The View of the Other Circuits
Although the Fifth Circuit has not addressed this question, other circuits
have. The other circuit decisions, as discussed below, have held that there
must be more than just explicit sex talk to support a § 2422(b) conviction.
These courts have upheld criminal convictions when the defendant and the
minor victim (or victim’s guardian) have at least began to make arrangements
to meet.
For instance, the Ninth Circuit in United States v. Goetzke, 494 F.3d
1231 (9th Cir. 2007) (per curiam) affirmed a defendant’s § 2422(b) conviction
in the absence of travel. There, a mother sent her developmentally disabled
10-year-old son to a Montana ranch owned by a family friend. Id. at 1233. A
few days into the trip, the mother learned that the defendant—a registered sex
offender with a sexual preference for young boys—was staying at the ranch as
well. Id. Accordingly, the mother had a social worker put her son on a plane
back to their home in Louisiana. Upon the boy’s return, the defendant began
calling and writing the young boy, promising Nintendo 64 video games, making
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explicit sexual overtures, and asking for pictures. Id. The mother turned the
correspondence over to authorities, who posed as the boy and responded
mimicking his writing style. Id. The defendant sent more sexual letters and
proposed a meeting: “[S]oon school will be out. Are you going to come to
Montana again? Maybe this summer?” Id. at 1233–34. After this letter, the
police arrested the defendant.
The Ninth Circuit affirmed the conviction and reasoned that the
defendant’s sexual letters “essentially began to ‘groom’ [the minor victim] for a
sexual encounter in the event he returned to Montana.” Id. at 1235. This
grooming behavior plus the defendant’s specific discussions about travel and a
proposed meeting crossed the line between preparation and attempt. See id.
at 1237. The defendant “sent W letters replete with compliments, efforts to
impress, affectionate emotion, sexual advances, and dazzling incentives to
return to Montana, and proposed that W return during the upcoming summer.
In short, [the defendant] made his move.” Id. (footnote omitted). The court
also noted that “[b]ecause Goetzke’s letters proposed that W return to
Montana, we need not decide whether an attempt to arrange a meeting is
required to constitute a substantial step under § 2422(b).” Id. at 1237 n.5.
To our knowledge, the only circuit to reverse a § 2422(b) conviction is the
Seventh Circuit in United States v. Gladish, 536 F.3d 646 (7th Cir. 2008).
There, the government caught the defendant in a sting operation in which a
government agent impersonated a 14-year-old girl in an internet chatroom.
The exchanges were graphic, and the defendant sent a video of himself
masturbating. The girl agreed to have sex with the defendant, and in a
subsequent chat, he discussed the possibility of traveling to meet her in a
couple of weeks, but no specific arrangements were made. Id. at 648.
The Seventh Circuit distinguished the Ninth Circuit’s decision in
Goetzke and reversed. Id. at 649–51. The court explained, “The substantial
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step can be making arrangements for meeting the girl, as by agreeing on a time
and place for the meeting.” Id. at 649 (citations omitted). Further, “[i]t can be
taking other preparatory steps, such as making a hotel reservation, purchasing
a gift, or buying a bus or train ticket, especially one that is nonrefundable.” Id.
The court noted that this conclusion was consistent with the Ninth Circuit’s
decision in Goetzke and that the court would not “try to give an exhaustive list
of the possibilities.” Id. The court also noted that “[c]hild sex abuse is often
effectuated following a period of ‘grooming’ and the sexualization of the
relationship.” Id. (quoting Sana Loue, Legal and Epidemiological Aspects of
Child Maltreatment, 19 J. Legal Med. 471, 479 (1998)).
The Seventh Circuit rejected the government’s argument that “the line
runs between ‘harmless banter’ and a conversation in which the defendant
unmistakably proposes sex.” Id. at 649. The court reasoned that in all the
cases that the government cited and that the court independently found “there
was more than . . . [just] explicit sex talk.” Id. “The Goetzke decision,” the
Seventh Circuit said, “goes the farthest in the direction of the government’s
opinion but is distinguishable.” Id. “Because Goetzke and his intended victim
had a prior relationship, his effort to lure the victim back to Montana could not
be thought idle chatter.” Id. at 650. “Treating speech (even obscene speech)
as the ‘substantial step’ would abolish any requirement of a substantial step,”
and that requirement “serves to distinguish people who pose real threats from
those who are all hot air.” Id.
The Seventh Circuit’s view in Gladish—that there must be more than
just explicit sex talk, such as an arrangement to meet—appears to be
consistent with the view of the other circuits. For example:
• The First Circuit affirmed a conviction under § 2422(b) and held that
the defendant “actually meeting with the girl’s father and discussing
with him graphic sexual details and prices goes far beyond ‘mere
preparation.’” United States v. Berk, 652 F.3d 132, 140 (1st Cir. 2011).
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• The Second Circuit affirmed a conviction concluding the defendant
“took a ‘substantial step’ towards the completion of the crime because
[he] actually went to the Port Authority bus terminal, the meeting
place that he had established with ‘Julie.’” United States v. Brand,
467 F.3d 179, 204 (2d Cir. 2006).
• The Third Circuit affirmed a conviction in which the defendant
“arranged a rendezvous [on a specific date] for the sexual encounter
and discussed ways to avoid police detection.” United States v. Nestor,
574 F.3d 159, 161 (3d Cir. 2009).
• The Fourth Circuit affirmed a conviction where the defendant,
“Engle[,] communicated with K.M. and C.M. in specific terms
regarding his expected release from jail, his immediate plan to reunite
with K.M., and his desired living arrangement in their house.
Moreover, Engle referenced his past sexual activity with K.M. in
graphic terms, and he unequivocally stated his intention to resume
sexual activity with her as soon as he was released.” United States v.
Engle, 676 F.3d 405, 423 (4th Cir.), cert. denied, 133 S. Ct. 179 (2012).
• The Eighth Circuit upheld a conviction where the defendant said, “he
just traveled to the meeting place ‘out of curiosity’ to see if there were
television cameras. He admitted using Yahoo! to chat with the
apparent minor. He admitted removing his photograph from his
profile following his trip to the apartment. He said he never intended
to have sex with a minor. A computer forensic analysis of Helder’s
desktop computer revealed that he had used MapQuest.com to search
for ‘lisa’’s address and had accessed her Yahoo! profile.” United States
v. Helder, 452 F.3d 751, 752 (8th Cir. 2006).
• And the Eleventh Circuit upheld a conviction where the defendant
“called Lynn on the telephone and, after hearing her voice, made
arrangements to meet her so they could engage in sexual activity.”
United States v. Yost, 479 F.3d 815, 820 (11th Cir. 2007).
Other courts have affirmed convictions where the defendant did not
actually make a definite plan to meet but proposed or began arranging a
meeting. See, e.g., United States v. Thomas, 410 F.3d 1235, 1246 (10th Cir.
2005) (upholding a conviction because the defendant “crossed the line from
‘harmless banter’ to inducement the moment he began making arrangements
to meet angelgirl12yo, notwithstanding the lack of evidence that he traveled to

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No. 13-40767
the supposed meeting place.”); United States v. Bailey, 228 F.3d 637, 639–40
(6th Cir. 2000) (upholding a conviction where the “minor testified that [the
defendant] e-mailed her his pager number and his private pin number for the
pager and that he urged her to call him and arrange a meeting. [The victim],
whose report prompted the investigation of [the defendant], testified that she
became frightened when [the defendant] sent her a message identifying her
hair color, what she had worn to school that day, and the time during which
she ate lunch at school.”). 8 Importantly, each of these decisions affirmed the
conviction. In none of these cases did the court say “this is the outer limit—
this far and no further.”
The case that most supports the government’s position is United States
v. Lee, 603 F.3d 904 (11th Cir. 2010). The Eleventh Circuit in Lee held that
“[w]e will not require firm plans to travel where, as here, the defendant, for
several months, took other steps sufficient to achieve the end which is the
object of the attempt.” Id. at 915. Lee shares many factual similarities with
the facts in this case. Both Lee and this case involve the undercover police
officer–adult intermediary of two fictional underage girls. 9 Like Howard, the
defendant in Lee sent photos of his penis to the undercover police officer, posing
as the girls’ mother, and asked that those photos be shared with the girls. Id.
at 917. He also asked about the girls’ reactions to the photos, demanded nude
photographs of the girls, and pressed the undercover officer to procure birth
control “because he is ‘not a condom user.’” Id. He also invited the undercover

8 There were three minor victims in Bailey and (it appears) only one count for violation
of § 2422(b) involving all three victims. The opinion summarizes the evidence for all three
victims, so it is unclear which evidence the court deemed sufficient. See Bailey, 228 F.3d at
639–40. That said, the court noted: “Several e-mails wherein [Bailey] proposed meeting the
girls to perform oral sex were read into the record.” Id. at 640.
9 Communicating through an adult intermediary is not a defense to § 2422(b).

Caudill, 709 F.3d at 447.
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No. 13-40767
officer to watch a live video stream of him masturbating, ending the video by
asking her to “send[] [his] lov[e]” to the girls. Id. Ultimately, the defendant in
Lee was arrested on his front porch “excitedly accepting what he believed to be
pornographic photographs of the minor girls.” Id.
But Lee is different from this case in some important respects. Howard’s
correspondence with the undercover officer here was over the course of three
weeks; whereas, the defendant in Lee communicated with the undercover
officer there over the course of eleven months. See id. at 915. Unlike Howard,
the defendant in Lee literally took a “step” to his front porch to accept delivery
of what he believed to be pornographic pictures of the minor girls.
Moreover, we note that “grooming behavior” is a factor other courts have
found significant in some cases. See, e.g., United States v. Chambers, 642 F.3d
588, 593 (7th Cir. 2011) (“We recognize that child sexual abuse can be
accomplished by several means and is often carried out through a period of
grooming.”); Lee, 603 F.3d at 915 (“Much of Lee’s conduct—especially his
sending graphic photographs to the girls and promising gifts—also supports a
finding that he groomed the girls in an effort to facilitate a future sexual
encounter.”); Goetzke, 494 F.3d at 1235 (“The [defendant’s] letters essentially
began to ‘groom’ W for a sexual encounter in the event he returned to
Montana.”). The Seventh Circuit defined “grooming” as “deliberate actions
taken by a defendant to expose a child to sexual material; the ultimate goal of
grooming is the formation of an emotional connection with the child and a
reduction of the child’s inhibitions in order to prepare the child for sexual
activity.” Chambers, 642 F.3d at 593 (citing Sana Loue, Legal and
Epidemiological Aspects of Child Maltreatment, 19 J. Legal Med. 471, 479
(1998)). The presence of grooming behavior is probative evidence that supports

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the inference that the defendant intends to entice the minor to assent to illegal
sex. 10
3. Analysis
The case law from this circuit and our sister circuits supports the rule
that grooming behavior plus other acts strongly corroborative of intent to
entice illegal sex—such as detailed discussions to arrange a meeting with the
minor victim—can suffice to establish a substantial step under § 2422(b). See,
e.g., Lee, 603 F.3d at 915 (“We will not require firm plans to travel where, as
here, the defendant, for several months, took other steps sufficient to achieve
the end which is the object of the attempt.”); cf. Broussard, 669 F.3d at 550
(“[W]e have never ruled that physical proximity or travel or plans to travel is
necessary to constitute a substantial step under § 2422(b).”). For example, in
Goetzke, the court affirmed the conviction where the defendant’s sexual
overtures essentially groomed the young boy for a sexual encounter, and held
that this grooming behavior plus the defendant’s proposed summer meeting in
Montana and prior relationship with the minor together support the jury’s
conclusion that Goetzke took a substantial step. 494 F.3d at 1235–37.
Accordingly, we disagree with the district court’s conclusion that Howard
took a substantial step toward enticing a minor to engage in illegal sex simply
by sending a sexually explicit photograph of himself and asking that it be
shown to the girls. Gladish and Lee are persuasive on this point. In both cases
the defendants sent video of themselves masturbating; the defendant in

Cf. United States v. Joseph, 542 F.3d 13, 18 (2d Cir. 2008) (reversing and remanding
10

on an erroneous jury instruction, reasoning: “[T]he offense remains ‘enticing,’ and making a
sexual act ‘more appealing’ in the absence of an intent to entice is not a crime. If jurors
thought that Joseph only wanted to make ‘Julie’ think that sexual conduct with him would
be appealing, but did not intend to entice her to engage in such conduct with him, they would
have convicted him for having cybersex conversation, which is not a crime, but not for
violating section 2242(b).” (footnote omitted)).
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Gladish sent the video directly to an undercover agent whom he thought was
a minor herself. But neither the Seventh Circuit in Gladish nor the Eleventh
Circuit in Lee found that behavior alone was sufficient to affirm the
convictions. Gladish, 536 F.3d at 651; see Lee, 603 F.3d at 916–18 (listing the
defendant’s having invited the undercover officer, posing as a minor’s mother,
to watch a live video stream of him masturbating as one of twenty-three pieces
of evidence which, “‘taken as a whole,’ allowed the jury to find that Lee’s
conduct was criminal.”). Thus, sending sexually explicit images and video is
probative evidence of intent to entice a minor to engage in illegal sex. But we
conclude this is not sufficient of itself to constitute a “substantial step.”
We also reject Howard’s argument that, under the Seventh Circuit’s
decision in Gladish, travel or a definite plan to travel is required to sustain a
conviction under § 2422(b). Answering the question we left open in Broussard,
we hold that travel or a definite plan to travel is not necessary to constitute a
“substantial step” under § 2422(b). Our view is consistent with persuasive
authority from our sister circuits. In Goetzke, the Ninth Circuit affirmed the
defendant’s conviction where the defendant proposed a summer meeting in
Montana and lured the minor victim with “dazzling incentives” that
“essentially began to ‘groom’” the victim “for a sexual encounter.” 494 F.3d at
1235, 1237. And in Bailey, the Sixth Circuit affirmed the defendant’s
conviction where the defendant “urged [the minor victim] to call him and
arrange a meeting.” 228 F.3d at 639–40.
Further, accepting Howard’s proposed bright-line rule—requiring an
unequivocal commitment, like purchasing a plane ticket—would allow internet
predators to look for vulnerable targets and escape criminal liability by simply

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avoiding concrete commitments through circumspection. We do not think that
Congress—or the court in Gladish—intended that result. 11
Here, we find that a reasonable trier of fact could conclude beyond a
reasonable doubt that Howard’s conduct approached the line between
despicable lawful conduct and criminal attempt—through his sexually explicit
conversations, transmission of sexual photographs, and discussion of specific
travel details—and crossed it when he instructed the undercover police officer
to perform sex acts on and procure birth control for the girls to get them ready
for him. The district court reasonably credited Detective Escobar’s testimony
that this conduct constituted “grooming behavior.” Cf. Chambers, 642 F.3d at
593 (defining “grooming behavior” as “deliberate actions taken by a defendant
to expose a child to sexual material; the ultimate goal of grooming is the
formation of an emotional connection with the child and a reduction of the
child’s inhibitions in order to prepare the child for sexual activity”). We view
this evidence in the light most favorable to the bench trial verdict of guilt.
Thus, a rational trier of fact could have found that Howard’s “grooming

11 We also reject Howard’s invocation of the rule of lenity “to the extent there is any
ambiguity in the ‘attempt language’” in § 2422(b). “The rule of lenity requires ambiguous
criminal laws to be interpreted in favor of the defendants subjected to them.” United States
v. Santos, 553 U.S. 507, 514 (2008) (Scalia, J., plurality opinion). The term “attempt” is not
subject to competing interpretations. Black’s Law Dictionary defines “attempt,” as that term
is used in criminal statutes, to mean: “An overt act that is done with the intent to commit a
crime but that falls short of completing the crime. . . . Under the Model Penal Code, an
attempt includes any act that is a substantial step toward commission of a crime . . . .” Black’s
Law Dictionary 146 (9th ed. 2009). Accordingly, “attempt” has acquired a common meaning
in the provisions of the federal criminal code, and, as discussed above, federal courts
consistently apply the Model Penal Code’s definition. Cf. Santos, 554 U.S. at 511 (applying
the rule of lenity in part because the term “proceeds” “has not acquired a common meaning
in the provisions of the Federal Criminal Code.”). We note our view is consistent with the
view of the First Circuit. See Dwinells, 508 F.3d at 70 (“Because the rule of lenity applies
only when the meaning of a criminal statute is genuinely uncertain, the rule simply does not
pertain [to interpretation of 18 U.S.C. § 2422(b)].”). In short, the difficulty in applying the
Model Penal Code’s “substantial step” test to the facts in this case does not indicate the
statute is ambiguous, so the rule of lenity has no application here.
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behavior”—against the backdrop of Howard’s conversations with Cabrielez 12
and together with his specific discussions about travel and transmittal of
sexually explicit photographs with instructions they be shown to the girls—
constituted a substantial step. See Allen, 587 F.3d at 256 (“[E]vidence is
sufficient to sustain a conviction if any rational trier of fact could have found
that the evidence established guilt beyond a reasonable doubt. This court
examines the evidence as a whole and construes it in the light most favorable
to the verdict.” ).
We disagree with Howard’s argument that this case is like Gladish
because Howard “made no flight or hotel reservations for Corpus Christi, any
agreement regarding a specific date to meet in Corpus Christi or any other
travel arrangements.” Cf. Gladish, 536 F.3d at 649 (“The substantial step can
be making arrangements for meeting the girl, as by agreeing on a time and
place for the meeting[,] [or] taking other preparatory steps, such as making a
hotel reservation, purchasing a gift, or buying a bus or train ticket, especially
one that is nonrefundable.” (citations omitted)). Gladish is distinguishable.
The discussions about travel in this case included Howard’s statement that “he
would definitely travel to Corpus Christi to have sex with [Detective Escobar’s]
daughter.” Howard asked what airport he should fly into, mentioned he could
fly Southwest Airlines, and inquired about specific hotels.
We find these detailed discussions more specific than the defendant’s
discussions about the mere “possibility of traveling to meet [the minor female]
in a couple of weeks” in Gladish. See 536 F.3d at 648. Further, these
discussions, importantly, occurred against the backdrop of Howard’s earlier
conversation with Cabrielez in which he offered her $5,000 to procure a

12 As discussed above, Howard offered Cabrielez $5,000 to procure a 15-year-old girl
for sex.
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No. 13-40767
“quince,” i.e., a fifteen-year-old girl. 13 Moreover, Howard not only sent sexually
explicit photographs, he specifically instructed Detective Escobar to perform
sex acts on, and procure birth control for, the minor girls. This conduct is
consistent with grooming behavior and is different from the facts in Gladish in
which the court found that “hot air is all the record shows.” Id. We think
Howard’s “grooming behavior”—particularly instructing Detective Escobar to
perform sex acts on and procure birth control for her minor daughters—plus
his detailed travel discussions sufficiently distinguishes him “from those who
are all hot air” and supports the verdict that he took a substantial step. See
id. at 650.
That said, we find the government’s conduct in the criminal investigation
curious. Detective Escobar seemingly asked the defendant to “put up, or shut
up”: she asked Howard to commit to book a flight before she would let him talk
to her minor daughters, “take it or leave it,” and Howard responded, “okay, I’ll
leave it.” Three months later—without Detective Escobar receiving any
further contact from Howard—the police arrested the bedridden Howard at his
girlfriend’s home in California.
In light of the government’s conduct, finding criminal attempt in this
case is a close call, and we hope that this is the outer bounds of a case the
government chooses to prosecute under § 2422(b). There is no single action by
the defendant in this case that clearly signifies that the defendant would follow
through on his sexual talk, “such as making a hotel reservation, purchasing a
gift, or buying a bus or train ticket, especially one that is nonrefundable,”

13 The Seventh Circuit in Gladish placed the defendant’s conduct in Goetzke in context
and noted that “[b]ecause Goetzke and his intended victim had a prior relationship, his effort
to lure the victim back to Montana for sex could not be thought idle chatter.” Gladish, 536
F.3d at 650. Here, Howard’s request that Cabrielez procure a fifteen-year old for sex, viewed
in the light most favorable to the verdict, supports the inference that Howard’s later
discussions with Detective Escobar were, similarly, not merely idle chatter.
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Gladish, 536 F.3d at 649 (noting that the court would not “try to give an
exhaustive list of the possibilities”), or even “accepting what he believed to be
pornographic photographs of the minor girls,” Lee, 603 F.3d at 917. A
discussion about price or a specific agreement would also be strong probative
evidence. Cf. Berk, 652 F.3d at 140 (holding that “actually meeting with the
girl’s father and discussing with him graphic sexual details and prices goes far
beyond ‘mere preparation.’”). Were we the triers of fact, we might reach a
conclusion different from the district court in this case.
But the district court had the benefit in this case of listening to live
testimony, including Howard’s testimony explaining himself. The court also
listened to and evaluated numerous recordings revealing the tone and
demeanor of the conversations between Detective Escobar and Howard. On
review of a bench trial verdict, our role is limited to determine whether the
district court’s finding of guilt is “supported by any substantial evidence.”
Allen, 587 F.3d at 256. Having examined the evidence as a whole in the light
most favorable to the verdict, we find that it is. 14
B. Howard’s Constitutional Challenges
Howard challenges the constitutionality of § 2422(b) on two grounds. He
asserts (1) that the term “attempt” is unconstitutionally vague and (2) that
§ 2422(b) is unconstitutionally overbroad because it criminalizes protected
speech in violation of the First Amendment. The government argues § 2422(b)
is not unconstitutionally vague or overbroad, noting that the Second, Third,

14 The role of the district judge is critical in these cases. The court must take care to
instruct juries to set aside their prejudices and to focus on the objective conduct of the
defendant as part of a course of conduct planned to culminate in his commission of the crime.
See Oviedo, 525 F.2d at 884–85 (the substantial step requirement “prevents the conviction of
persons engaged in innocent acts on the basis of a mens rea proved through speculative
inferences, unreliable forms of testimony, and past criminal conduct”). If the district judge
is the fact finder, he or she must similarly find the facts based on the objective evidence. We
are confident the district court did that here.
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Sixth, Ninth, Tenth, and Eleventh Circuits “have analyzed the statute and
rejected similar constitutional challenges.” We agree with the government.
First, we note that we review Howard’s vagueness challenge for plain
error because he did not present this issue to the district court. See Knowles,
29 F.3d at 950. In contrast, Howard presented his overbreadth challenge to
the district court, so our review of that issue is de novo. Clark, 582 F.3d at 612.
Under basic principles of due process, a criminal statute is void for
vagueness if the conduct it prohibits is not clearly defined. Grayned v. City of
Rockford, 408 U.S. 104, 108 (1972). To satisfy constitutional due process, “a
penal statute [must] define the criminal offense [1] with sufficient definiteness
that ordinary people can understand what conduct is prohibited and [2] in a
manner that does not encourage arbitrary and discriminatory enforcement.”
Skilling v. United States, 561 U.S. 358, 403 (2010) (alterations in original)
(internal quotation marks omitted) (quoting Kolender v. Lawson, 461 U.S. 352,
357 (1983)). “The overbreadth doctrine prohibits the Government from
banning unprotected speech if a substantial amount of protected speech is
prohibited or chilled in the process.” Ashcroft v. Free Speech Coal., 535 U.S.
234, 255 (2002).
Although the Fifth Circuit has not yet had occasion to address
constitutional challenges to § 2422(b), the government is correct that the other
circuits have unanimously upheld § 2422(b) over vagueness and overbreadth
challenges. 15 For example, in United States v. Hart, the Sixth Circuit rejected

15 United States v. McMillan, 744 F.3d 1033, 1036 (7th Cir. 2014) (“In the end, what
is important under this statute is the defendant’s attempt (using the mails or other
instrumentalities of commerce) to persuade the minor. So read, there is nothing
unconstitutionally vague about this law, contrary to McMillan’s protestations. Ordinary
people using common sense . . . will understand that § 2422(b) is violated by attempts to
persuade, entice, coerce, or induce a minor to engage in sexual activity.” (citations and
internal quotation marks omitted)); United States v. Gagliardi, 506 F.3d 140, 147 (2d Cir.
2007) (rejecting the defendant’s argument that § 2422(b) is unconstitutionally vague because
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an overbreadth challenge to § 2422(b) because “(1) the statute applies only to
persons who knowingly attempt to persuade minors to engage in sexual
activity, and (2) a defendant ‘does not have a First Amendment right to attempt
to persuade minors to engage in illegal sex acts.’” 635 F.3d 850, 857 (6th Cir.
2011) (quoting Bailey, 228 F.3d at 639). Moreover, the Supreme Court has said
in the First Amendment context that “[t]he prevention of sexual exploitation
and abuse of children constitutes a government objective of surpassing
importance.” New York v. Ferber, 458 U.S. 747, 757 (1982) (upholding a New
York statute that prohibits the distribution of hard core child pornography over
a First Amendment overbreadth challenge). And in United States v. Gagliardi,
506 F.3d 140 (2d Cir. 2007), the Second Circuit rejected the defendant’s
argument that § 2422(b) was unconstitutionally vague because the word
attempt is a “word[] of common usage that ha[s] [a] plain and ordinary
meaning[].” Id. at 147. The court explained “the statute’s terms are
sufficiently definite that ordinary people using common sense could grasp the
nature of the prohibited conduct.” Id. The court also observed § 2422(b)
“establishes the requisite minimal guidelines to prevent arbitrary or
discriminatory enforcement in that it applies only to those who ‘knowingly’

it does not define the term “attempt” because the term is “sufficiently definite that ordinary
people using common sense could grasp the nature of the prohibited conduct”); see also United
States v. Hart, 635 F.3d 850, 858 (6th Cir. 2011) (rejecting vagueness challenge because “the
term ‘persuade’ in 18 U.S.C. § 2422(b) has an ordinary meaning that is not subject to
ambiguity”); United States v. Tykarsky, 446 F.3d 458, 473 (3d Cir. 2006) (“[W]e also conclude
that § 2422(b) is not unconstitutionally vague. Although § 2422(b) does not define the terms
‘persuade,’ ‘induce,’ ‘entice’ and ‘coerce,’ they ‘have a plain and ordinary meaning that does
not need further technical explanation.’”); United States v. Thomas, 410 F.3d 1235, 1244
(10th Cir. 2005) (“Section 2422(b) requires only that the defendant intend to entice a minor,
not that the defendant intend to commit the underlying sexual act. Contrary to Thomas’s
assertions, this interpretation does not render the statute unconstitutionally overbroad or
void for vagueness.”); United States v. Panfil, 338 F.3d 1299, 1301 (11th Cir. 2003) (per
curiam) (rejecting vagueness challenge because “[s]ection 2242(b) suffers from no such
constitutional infirmity. The words ‘entice’ and ‘induce’ are not ambiguous or subject to
varying standard . . . . Indeed, the language of § 2422(b) is clear.” (citation omitted)).
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engage in the prohibited conduct.” Id. (citation omitted) (citing Kolender, 461
U.S. at 358). “This scienter requirement,” the court explained, “narrows the
scope of § 2422(b) as well as the ability of prosecutors and law enforcement
officers to act based on their own preferences.” Id.
We find this authority persuasive. As discussed briefly above, 16 the term
“attempt” has acquired an ordinary, definite, and plain meaning in the
criminal context. See Black’s Law Dictionary 146 (9th ed. 2009). Further,
§ 2422(b)’s scienter requirement sufficiently constrains government discretion.
See Kolender, 461 U.S. at 358; Gagliardi, 506 F.3d at 147. In the absence of
Fifth Circuit authority to the contrary, and in light of the unanimous
persuasive authority upholding the constitutionality of § 2422(b), Howard has
not shown that any error on the vagueness issue was plain. See United States
v. Clark, 582 F.3d 607, 614 (5th Cir. 2009) (rejecting a vagueness challenge
because the defendant did not “show that an ordinary person cannot
understand what conduct [the statute] prohibits or that the statute encourages
arbitrariness and discrimination by law enforcement”).
We reach the same conclusion with respect to Howard’s overbreadth
challenge. Here, Howard has not shown that, viewing the evidence in the light
most favorable to the prosecution, he was engaged in protected speech. The
judge, sitting as trier of fact, found that he knowingly attempted to persuade
minors to engage in illegal sex acts. As the Sixth and Eleventh Circuits have
observed, “[s]peech attempting to arrange the sexual abuse of children is no
more constitutionally protected than speech attempting to arrange any other
type of crime.” United States v. Hornaday, 392 F.3d 1306, 1311 (11th Cir.
2004); see also Ferber, 458 U.S. at 764 (“When a definable class of material . . .
bears so heavily and pervasively on the welfare of children engaged in its

16 See supra note 11.
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production, we think the balance of competing interests is clearly struck and
that it is permissible to consider these materials as without the protection of
the First Amendment.”). Thus, we agree with our sister circuits and hold that
§ 2422(b) is not unconstitutionally overbroad because it does not criminalize
protected speech in this case.
IV. CONCLUSION
For the foregoing reasons, we AFFIRM.

27