United States v. Carlo Castro

PRECEDENTIAL
UNITED STATES COURT OF APPEALS
FOR THE THIRD CIRCUIT
_____________

No. 11-3893
_____________

UNITED STATES OF AMERICA

v.

CARLO DANIEL CASTRO,
Appellant.
_______________

On Appeal from the United States District Court
for the Eastern District of Pennsylvania
(D.C. No. 10-cr-732)
District Judge: Hon. Harvey Bartle, III
_______________

Argued
September 25, 2012

Before: McKEE, Chief Judge, JORDAN, and VANASKIE,
Circuit Judges.

(Filed: January 8, 2013)
_______________
Peter Goldberger [ARGUED]
50 Rittenhouse Place
Ardmore, PA 19003
Counsel for Appellant

Louis D. Lappen [ARGUED]
Office of United States Attorney
615 Chestnut Street - #1250
Philadelphia, PA 19106
Counsel for Appellee
_______________

OPINION OF THE COURT
_______________

JORDAN, Circuit Judge.

Daniel Castro, a high-ranking official in the
Philadelphia Police Department, was indicted in connection
with three separate schemes to extort money from separate
individuals by use of violence. He was convicted by a jury on
one count of making a material false statement to federal
agents in violation of 18 U.S.C. § 1001, and acquitted on one
count of conspiracy to commit extortion in violation of 18
U.S.C. § 894. The jury hung on the remaining eight counts.

To avoid a retrial, Castro pled guilty to a count of
conspiracy to commit extortion in violation of 18 U.S.C.
§ 1951. In exchange the government agreed to dismiss the
remaining charges against him. Castro‟s plea agreement
contained an appellate waiver provision under which, subject
to some exceptions, he “voluntarily and expressly waive[d]
all rights to appeal or collaterally attack” his “conviction,

2
sentence, or any other matter relating to this prosecution.”
(App. at 127.) The District Court sentenced him to
concurrent sentences of 18 months in prison for his
conviction for false statements and 60 months in prison for
his conviction by guilty plea for conspiracy to commit
extortion.

In this appeal, Castro challenges three facets of his
conviction and sentence. First, he contends that there was
insufficient evidence to convict him of making a false
statement to the FBI about money allegedly received from an
extortion victim. He argues that, because the money in
question came from the FBI in the course of a sting operation,
he told the literal truth when he denied having received any
money from the alleged victim. Second, Castro challenges
the District Court‟s authority to deny the government‟s
motion, made pursuant to § 3E1.1(b) of the United States
Sentencing Guidelines, for a one level decrease in his offense
level calculated under the guidelines. Third, Castro maintains
that, in arriving at a sentence that was 19 months higher than
the top of the range recommended by the guidelines, the
District Court failed to adequately account for his record of
good works. The government responds that Castro‟s first two
arguments are barred by his appellate waiver and that, as to
the third argument, Castro cannot show that the sentence is
unreasonable.

We conclude that the appellate waiver encompasses
both Castro‟s challenge to the sufficiency of the evidence and
his claim that the District Court lacked authority to deny the
government‟s motion for a one level decrease in his offense
level. However, while the waiver properly applies to prevent
our considering the District Court‟s refusal to award the

3
requested downward departure, we conclude that application
of the waiver against the sufficiency-of-the-evidence
argument would, in the unusual circumstances of this case,
work a miscarriage of justice. We will therefore vacate
Castro‟s conviction and 18-month sentence for making a false
statement to federal agents. We will also vacate Castro‟s 60-
month sentence because the invalid conviction for false
statements was included in calculating Castro‟s overall
offense level, causing that level to be higher than it otherwise
would have been and resulting in a sentencing range that is no
longer applicable. We are accordingly not in a position to
evaluate Castro‟s reasonableness challenge, and we will
remand the case to the District Court for resentencing solely
on the conviction for conspiracy to commit extortion.

I. Background

A. Facts

Castro rose from challenging circumstances to become
one of the highest ranking officers in the Philadelphia Police
Department. During his 25 years of service as a policeman,
he received numerous accolades and advancements, only a
handful of which we mention here. In 1997, he was promoted
to Captain. In 2001, he was nominated by the then-Mayor of
Philadelphia, Edward Rendell, and Police Commissioner John
Timoney to represent the Philadelphia Police Department as
an Eisenhower Fellow, an important position that placed
Castro in contact with community leaders from business,
academia, and political and non-profit organizations, and
allowed him to be part of international leadership mentoring
programs. And in 2010, he was promoted to the position of
Inspector, a high-ranking position within the police force. By

4
all accounts, Castro was well regarded within the Philadelphia
Police Department, and, as noted below, he saw himself as a
viable candidate to one day become police commissioner.
His successes and substantial authority make his subsequent
criminal behavior all the more disturbing and damning.

In 2006, Castro invested $90,000 in a residential real
estate development project organized by an acquaintance
named Wilson Encarnacion. When the project failed, Castro
repeatedly and unsuccessfully sought repayment from
Encarnacion. The lost investment represented Castro‟s life
savings.

In 2010, Castro discussed with another acquaintance,
Rony Moshe, his frustration over the personally disastrous
investment. Moshe mentioned that he knew a couple of tough
debt collectors, and Castro asked if Moshe could engage the
collectors to pressure Encarnacion to repay Castro‟s losses –
losses that Castro evidently thought of as a debt Encarnacion
owed him. Unbeknownst to Castro, Moshe was an FBI
informant. He reported his conversation with Castro to the
FBI, and an investigation was launched. At the FBI‟s behest,
Moshe began secretly recording telephone conversations and
in-person meetings with Castro. The undercover operation
ran from April through November of 2010.

On April 7, 2010, Moshe told Castro in a series of
recorded telephone calls that he had found a “collector” for
Castro who was willing to collect the $90,000 debt from
Encarnacion. Although Castro‟s loss on the failed investment
was $90,000, he instructed Moshe to have the collector
demand $150,000. When Moshe told Castro that the collector
would use threatening and intimidating collection methods,

5
Castro responded that he did not want to know the specific
methods, that he did not want to meet the collector, and that
he did not want the collector to know Castro‟s identity.
Castro emphasized that he did not want to get “implicated
into this.” (App. at 1291.) But he went ahead and provided
Moshe with Encarnacion‟s home address, and he told Moshe
to send the collector there because Encarnacion‟s wife and
child would be there and “they‟ll get scared.” (App. at 346.)

Later, on June 4, Castro spoke by telephone with an
undercover FBI agent posing as the collector. In that
conversation, which was recorded, the agent told Castro that
he and an associate had obtained $5,000 from Encarnacion
and had $4,500 to give to Castro, with $500 being withheld as
a collection fee. The agent represented that Encarnacion had
initially denied owing Castro any money but relented after the
agent and his associate went inside Encarnacion‟s house and
the agent threatened Encarnacion by telling him that he would
“f--- his wife” if he refused to pay. (App. at 1321-23.)

On June 11, Castro met with Moshe, who gave Castro
the $4,500 supposedly collected from Encarnacion. Moshe
said that, following Encarnacion‟s encounter with the
collector, Encarnacion was “scared to death.” (App. at 3691.)
Castro replied, “Good, Good, Good.” (App. at 361.) Castro
acknowledged that the collector “mean[t] serious business,”
and he mentioned that he was concerned that Encarnacion
might go to the police. (App. at 1332-33, 360-62.)

Castro met with Moshe again on July 20, 2010, and
Moshe gave him another $2,100 that the collector had
supposedly obtained from Encarnacion. That money, like the
first payment, came from the FBI. There is no evidence that

6
Encarnacion was aware of the FBI‟s payments to Castro or
that the FBI‟s payments somehow reduced a debt actually
owed by Encarnacion. Moshe stated that if Castro wanted to
recover his money more quickly, the collector would have to
become “more aggressive.” (App. at 377.) Castro was
hesitant to authorize more aggressive tactics, telling Moshe,
“I can‟t get myself in trouble. … I want to be Police
Commissioner.” (App. at 564.) Nevertheless, Castro urged
Moshe to have the collector go back to Encarnacion‟s home
and collect more money – “$10,000 at a shot.” (App at 384.)

Around that time, the undercover operation paused for
nearly two months because Moshe suffered a stroke. In early
September 2010, Moshe and Castro resumed speaking and,
on September 10, Moshe told Castro that Encarnacion was
refusing to pay. Moshe asked Castro if he wanted the
collector to “rough him up.” (App. at 1369-70.) Castro
responded, “Well, get, get my money. I want, I want my
money. They, they, they, they know how to get it.” (App. at
1371.) When Moshe said that the collector might “break[] a
leg, a hand, you know,” Castro responded, “I don‟t, I don‟t
want the guy dead. I don‟t, I don‟t want to kill him.” (App.
at 1373-76.)

During that conversation Castro broached the topic of
a second debt collection effort. Castro told Moshe of two
acquaintances, business partners Billy Wong and Alan Kats,
who were looking to hire a debt collector. Moshe noted that,
to extract money, the collectors would have to get rough with
Wong‟s and Kats‟s debtor. Castro asked Moshe to meet with
Wong on September 15, 2010. Castro admitted in his
testimony at trial that he understood, as of that date but not
before, that the supposed collectors would batter Wong‟s and

7
Kats‟s debtor. He also acknowledged that he became aware
at that time that the collectors Moshe had engaged for him
would use threats of violence and, if necessary, actual
violence to get money from Encarnacion. (District Court
Docket Item (“D.I.”) 90:228-29 (Tr. 4/14/11) (Castro: “On
[September 10], I crossed the line … . Q: [Wong and Kats‟
debtor is] gonna get beaten, right? Just like [Encarnacion] –
gonna get beaten, isn‟t that right? A: You can safely
inference that, yes, sir.”)).

On September 15, 2010, Moshe met with Wong and
Kats, who explained that they needed help collecting $26,000
that had been lost in a failed nightclub investment. Moshe
told them about the collector whom he had used for Castro,
and Kats told Moshe to go ahead and engage the collector‟s
services. Wong and Kats understood that compelling their
“debtor” to pay would involve threats of violence and,
perhaps, actual violence. On September 22, Wong and Kats
met with an undercover FBI agent posing as the collector, and
Kats authorized the agent to use violence to collect the
money. Later, on October 1, 2010, the undercover agent gave
Kats $3,000 supposedly collected from the debtor, and
approximately a month after that, the agent similarly gave
Kats an additional $5,000.

On September 21, 2010, Moshe again spoke to Castro
about the effort to collect money from Encarnacion. He said
that the collectors had recovered a “pretty big chunk” of
money by getting “pretty rough” with Encarnacion. (App. at
400-01.) Castro replied, “They got the end result.” (App. at
401.) About one week later, Moshe gave Castro $14,000 out
of $15,000 that had supposedly been collected from
Encarnacion, plus a $500 “referral fee” for referring Wong

8
and Kats to the “collectors.” (D.I. 91:87-88 (Tr. 4/15); D.I.
137:22 (Plea).) During that meeting, Castro also told Moshe
of a third collection job to refer to the collectors, this time for
$1.5 million in Florida.

Soon thereafter, on October 4, 2010, FBI agent Brian
Nichilo and Detective Steve Snyder of the Philadelphia Police
conducted an unrecorded interview with Castro in which they
pretended to be investigating a complaint from Encarnacion
that he was being threatened in relation to a debt he owed.
According to Nichilo‟s testimony at trial, Castro claimed that
he had not discussed with anyone the collection of a debt
from Encarnacion,1 that he did not hire anyone to extort
money from Encarnacion,2 and that he had not received any
money from Encarnacion. Specifically, Nichilo testified that
he asked Castro “whether he had ever collected any money
from Mr. Encarnacion since he originally gave him the
$90,000 in 2006.” (App. at 105-06.) Castro responded,
according to Nichilo, that he had not collected any money
from Encarnacion. (App. at 106.) In his own trial testimony

1
Count Four, on which the jury hung, charged Castro
with making a false statement to the FBI in violation of 18
U.S.C. § 1001 when he “told FBI agents that, outside of [a
civil] lawsuit [against Encarnacion] and general complaining
to friends,” he had “not had any discussions with anyone
about how he could collect from [Encarnacion].” (App. at
40.)
2
Count Five, another count on which the jury hung,
charged Castro with making a false statement to the FBI by
stating that “he did not hire anyone to threaten or hurt
[Encarnacion] to collect the debt.” (App. at 41.)

9
regarding that interview with law enforcement officials,
Castro admitted that he had “lied” when he “told them I
didn‟t know anything about what they asked me,” (App. at
121), and that he did not “tell them the truth.” (App. at 906.)
But Castro denied making the particular statements recounted
by Nichilo.

On October 12, 2010, Castro described his meeting
with the FBI to Moshe. Castro instructed Moshe to cease
collecting money from Encarnacion “for right now” (App. at
407), but he asked Moshe to have the collectors go to Florida
to commence a collection effort there.

Castro was arrested on November 5, 2010. FBI agents
searched his home and recovered the money that he had
received from Moshe and that he had been told came from
Encarnacion.

B. Course of Proceedings

A federal grand jury in the Eastern District of
Pennsylvania returned a ten-count superseding indictment on
February 3, 2011, against Castro. Only two counts are of
importance to this appeal. Count Three charged that on
October 4, 2010, in violation of 18 U.S.C. § 1001, Castro
made a false statement to federal law enforcement officers in
connection with his efforts to collect money from
Encarnacion – specifically, “that he had not received any
payments from [Encarnacion] towards the debt [Encarnacion]
supposedly owed” him. (App. at 39.) Count Nine charged

10
Castro with conspiring with Wong and Kats to commit
extortion in violation of 18 U.S.C. § 1951.3

A jury convicted Castro on Count Three, acquitted him
on Count Ten, which charged the use of extortionate means to
collect a debt, in violation of 18 U.S.C. § 894, and returned a
hung verdict on the remaining eight counts. To avoid a
scheduled retrial, Castro entered into a plea agreement with
the government, pursuant to which he pled guilty to Count
Nine. The agreement included a broad waiver of his appellate
rights.

At sentencing, the parties agreed that the combination
of convictions on Counts Three and Nine led, under the
applicable sentencing guidelines, to a sentencing range of 30
to 37 months, based on an offense level of 19 and criminal
history category of I. The government also agreed to file a
motion seeking a three-level downward departure under
§ 3E1.1(b) of the guidelines. Pursuant to that provision of the
guidelines, the typical two-level reduction of a defendant‟s
offense level gained by accepting responsibility can become a
three-level reduction if the government files a motion stating
that “the defendant has assisted authorities in the
investigation or prosecution of his own misconduct by timely
notifying authorities of his intention to enter a plea of guilty,
thereby permitting the government to avoid preparing for trial

3
Wong, who was also charged in Counts Nine and Ten
of the superseding indictment, pled guilty to those counts and
agreed to testify against Castro. Kats was charged in a
separate indictment for his involvement in the extortion
scheme, and he pled guilty to attempted collection of credit
by extortionate means.

11
and permitting the government and the court to allocate their
resources efficiently[.]”4 When the government made that
motion in this case, however, the Court sua sponte rejected it,
making Castro‟s offense level 20 (instead of 19), and
accordingly making the guidelines range 33 to 41 months
(instead of 30 to 37 months). The Court then imposed an
upward variance to bring the sentence to 60 months in prison
on Count Nine, concurrent with 18 months on Count Three,
to be followed by three years of supervised release. The
Court also imposed a $10,000 fine and $200 in special
assessments.

Castro then filed this timely appeal.
4
Section 3E1.1 provides in full:
(a) If the defendant clearly demonstrates
acceptance of responsibility for his offense,
decrease the offense level by 2 levels.
(b) If the defendant qualifies for a decrease
under subsection (a), the offense level
determined prior to the operation of subsection
(a) is level 16 or greater, and upon motion of
the government stating that the defendant has
assisted authorities in the investigation or
prosecution of his own misconduct by timely
notifying authorities of his intention to enter a
plea of guilty, thereby permitting the
government to avoid preparing for trial and
permitting the government and the court to
allocate their resources efficiently, decrease the
offense level by 1 additional level.
U.S. Sentencing Guidelines Manual § 3E1.1.

12
II. Discussion5

Castro raises three arguments on appeal. First, he
contends that his conviction should be vacated because “there
was a complete failure of proof on Count Three,” which
charged him with “knowingly making a false statement to the
FBI” by lying when he denied that he had received any
money from Encarnacion in repayment of the $90,000 lost
investment. (Appellant‟s Br. at 16.) Castro argues that, in
fact, he “had not received any such repayments” from
Encarnacion but had instead received money from the FBI in
a sting operation. (Id.) Thus, he says, his denial “was not
„false,‟ much less „knowingly‟ so.” (Id.) He reasons that
since his denial was literally true, even if he did not
appreciate it as such, “the evidence was insufficient to convict
on Count Three,” and his conviction on that count must “be
vacated and the case remanded for resentencing on Count
Nine alone.” (Id.)

Second, Castro maintains that his sentence was
procedurally unreasonable because the District Court
erroneously denied the government‟s motion that his offense
level be reduced not just two points but three points for
“acceptance of responsibility” under the sentencing
guidelines. He argues that § 3E1.1(b) of the guidelines
confers upon the government, not the court, “the discretion …
to allow a third level of reduction,” (id.), and that this

5
The District Court had subject matter jurisdiction
under 18 U.S.C. § 3231, because the indictment alleged
offenses against the United States. We have jurisdiction
under 28 U.S.C. § 1291 and 18 U.S.C. § 3742(a).

13
discretion is entitled to “full deference.” United States v.
Drennon, 516 F.3d 160, 162 (3d Cir. 2008).

Third, Castro asserts that his 60-month sentence is
procedurally and substantively unreasonable because the
guidelines range determined by the District Court suggested a
period of imprisonment of 33 to 41 months. He argues that
the Court did not adequately take into account evidence of his
good character and failed to explain why such a harsh
sentence was necessary to fulfill the proper purposes of
sentencing.

The government responds that Castro‟s first two
challenges are barred by the appellate waiver contained in his
plea agreement. In the alternative, the government argues
that even if the appellate waiver does not foreclose Castro‟s
claims, neither issue was raised in the District Court, and
Castro cannot show that either of those claimed problems
rises to the level of plain error. The government concedes
that Castro‟s third argument is not barred by the appellate
waiver, but it argues that “Castro cannot show that no
reasonable court would have imposed such a sentence under
[the] circumstances” of this case. (Appellee‟s Br. at 24-25.)

In the sections that follow, we address each of Castro‟s
three arguments, with the first two arguments being affected
by his appellate waiver.

A. Sufficiency of the Evidence for Castro’s
Conviction for False Statements

Before addressing either of Castro‟s first two
contentions, we must first determine whether his appellate

14
waiver bars us from even considering them. As part of his
plea agreement, Castro generally agreed that he would neither
appeal nor present any collateral challenge to his conviction
or sentence. In pertinent part, the appellate waiver provides
that, “[i]n exchange for the undertakings made by the
government in entering this plea agreement, the defendant
voluntarily and expressly waives all rights to appeal or
collaterally attack the defendant‟s conviction, sentence, or
any other matter relating to this prosecution[.]” (App. at
127.) The waiver does, however, contain two exceptions that
are relevant to this appeal: first, the waiver does not “bar the
assertion of constitutional claims that the relevant case law
holds cannot be waived” (App. at 127); and, second, the
waiver allows appeal for “claims that … the sentencing judge,
exercising the Court‟s discretion pursuant to United States v.
Booker, 543 U.S. 220 (2005), imposed an unreasonable
sentence above the final Sentencing Guideline range
determined by the Court.” (App. at 128.)

“We exercise plenary review in deciding whether an
issue raised by a defendant falls within the scope of an
appellate waiver in his plea agreement.” United States v.
Goodson, 544 F.3d 529, 537 n.6 (3d Cir. 2008). When “the
government invokes an appellate-waiver provision … , we
must determine as a threshold matter whether … [that] waiver
prevents us from exercising our jurisdiction to review the
merits of the defendant‟s appeal.” United States v. Corso,
549 F.3d 921, 926 (3d Cir. 2008) (citations omitted). “We
decline to exercise jurisdiction over the appeal where [1] the
issues on appeal fall within the scope of the waiver and [2]
the defendant knowingly and voluntarily agreed to the waiver,
unless [3] „enforcing the waiver would work a miscarriage of
justice.‟” United States v. Saferstein, 673 F.3d 237, 242 (3d

15
Cir. 2012) (quoting Corso, 549 F.3d at 927); accord United
States v. Hahn, 359 F.3d 1315, 1325 (10th Cir. 2004) (en
banc).

Under the first prong, we evaluate the language of the
appellate waiver to determine if the disputed appeal falls
within its scope. We follow the “well-established principle
that plea agreements, although arising in the criminal context,
are analyzed under contract law standards.” Goodson, 544
F.3d at 535 n.3 (alteration and internal quotation marks
omitted). “[I]n light of those standards, the language of an
appellate waiver, like the language of a contract, matters
greatly to our analysis[.] [S]uch waivers must be strictly
construed.” Corso, 549 F.3d at 927 (citation, alteration, and
internal quotation marks omitted); cf. United States v.
Williams, 510 F.3d 416, 422 (3d Cir. 2007) (“In view of the
government‟s tremendous bargaining power courts will
strictly construe the text [of a plea agreement] against the
government when it has drafted the agreement.” (alterations
omitted)). “But we are also mindful that under contract
principles, a plea agreement necessarily works both ways.
Not only must the government comply with its terms and
conditions, but so must the defendant.” Corso, 549 U.S. at
927 (citations, alteration, and internal quotation marks
omitted). Accordingly, a defendant cannot “get the benefits
of his plea bargain, while evading the costs because contract
law would not support such a result.” Id. (alteration and
internal quotation marks omitted).

The second step in reviewing an appellate waiver is to
determine whether the waiver is knowing and voluntary.
“[T]he role of the sentencing judge is critical” in that regard,
United States v. Khattak, 273 F.3d 557, 563 (3d Cir. 2001),

16
because rule 11(b)(1)(N) of the Federal Rules of Criminal
Procedure provides that

Before accepting a plea of guilty or nolo
contendere, … the court must address the
defendant personally in open court. During this
address, the court must inform the defendant of,
and determine that the defendant understands
the following: … the terms of any plea-
agreement provision waiving the right to appeal
or to collaterally attack the sentence.

Fed. R. Crim. P. 11(b)(1)(N). We have held that “a statement
made by the sentencing court during the [plea] colloquy can
create ambiguity where none exists in the plain text of the
plea agreement,” Saferstein, 673 F.3d at 243, and such
ambiguity may result in a narrow construction of an appellate
waiver, “to protect the defendant as the weaker bargaining
party,” id.

The third and last step is to determine whether
enforcing the waiver would result in a miscarriage of justice.
When a waiver encompasses the issue on appeal and was
entered knowingly and voluntarily, it must be enforced except
in the “unusual circumstance” of “an error amounting to a
miscarriage of justice.” Khattak, 273 F.3d 562. Certain
factors weigh in the determination of whether a given error
meets that standard:

[T]he clarity of the error, its gravity, its
character (e.g., whether it concerns a fact issue,
a sentencing guideline, or a statutory

17
 maximum), the impact of the error on the
defendant, the impact of correcting the error on
the government, and the extent to which the
defendant acquiesced in the result.

Id. at 563 (internal quotation marks omitted). Courts apply
the “miscarriage of justice” exception “sparingly and without
undue generosity,” United States v. Wilson, 429 F.3d 455,
458 (3d Cir. 2005) (internal quotation marks omitted), but
with the aim of avoiding “manifest injustice,” United States v.
Gwinnett, 483 F.3d 200, 206 (3d Cir. 2007).6

6
It is not enough that an issue be meritorious:
[B]y waiving the right to appeal, a defendant
necessarily waives the opportunity to challenge
the sentence imposed, regardless of the merits.
… A waiver of the right to appeal includes a
waiver of the right to appeal difficult or
debatable legal issues – indeed, it includes a
waiver of the right to appeal blatant error.
Waiver would be nearly meaningless if it
included only those appeals that border on the
frivolous. … While it may appear unjust to
allow criminal defendants to bargain away
meritorious appeals, such is the necessary
consequence of a system in which the right to
appeal may be freely traded.
Khattak, 273 F.3d at 561-62 (internal quotation marks
omitted).

18
 1. Scope of the Appellate Waiver

This case presents a procedural anomaly. Ordinarily,
plea agreements are entered before any trial in a case, but
Castro entered his plea agreement in anticipation of a second
trial, after he had been tried once and convicted on one of ten
counts. Our first task in determining whether Castro‟s
appellate waiver should be enforced to prevent him from
challenging his conviction for the crime charged in Count
Three is to determine whether the waiver even encompasses
that conviction.

Castro asserts that the language of the appellate waiver
does not clearly apply to his conviction at trial. Because plea
agreements are to be “strictly construed” against the
government, Khattak, 273 F.3d at 562, he says that his
appellate waiver should not apply to his conviction on Count
Three. He cannot, however, wish away the words of the
waiver. The plea agreement provides that Castro “voluntarily
and expressly waives all rights to appeal or collaterally attack
[his] conviction, sentence, or any other matter relating to this
prosecution.” (App. at 127.) The breadth of the phrase “any
other matter relating to this prosecution” surely encompasses
Castro‟s earlier conviction on Count Three, and Castro‟s
attempt to argue otherwise is unavailing.

2. Knowing and Voluntary Waiver

But understanding the linguistic scope of the waiver is
only the first step in determining whether the waiver applies.
Castro claims that, during the Rule 11 colloquy, the District
Court did not mention his earlier conviction, and that he was
therefore under the impression that the waiver did not apply

19
to that conviction. Instead, says Castro, the Court
consistently emphasized that he was giving up his right to a
second trial and the right to appeal his sentence. Thus, Castro
argues, “it is at least reasonable to conclude that the plea
agreement did not concern the count on which there had
already been a full trial.” (Appellant‟s Reply Br. at 5.)

Although he does not say so explicitly, Castro appears
to be seeking shelter in our precedent that a judge‟s
affirmative statements during a plea colloquy can sometimes
overcome the otherwise plain terms of a plea agreement.7
Such judge-created “ambiguity” must be construed “against
the government,” Saferstein, 673 F.3d at 243, because, “[i]f it
is reasonable to rely upon the court‟s words for clarification,
then we cannot expect a defendant to distinguish and
disregard those statements of the court that deviate from the
language of a particular provision in a lengthy plea
agreement,” United States v. Wilken, 498 F.3d 1160, 1168
(10th Cir. 2007).

Castro‟s argument is an elaboration on that precedent.
He argues in essence that, by talking at length about the rights
he would give up by foregoing a second trial, the District
Court left him thinking that the waiver applied only
prospectively and not as to the already fixed history of the
case. He suggests, in other words, that it is not only a district
court‟s affirmative statements that can change the scope of a

7
As noted, we have held that, even when the written
terms of an appellate waiver are clear, “a statement made by
the sentencing court during the colloquy can create ambiguity
where none exists in the plain text of the plea agreement.”
Saferstein, 673 F.3d at 243.

20
plea agreement; a district court‟s emphases and omissions
during a plea colloquy may also alter the defendant‟s
understanding of the plain terms of the plea agreement. We
have never so held and we will not do so now.

Indeed, even if we were to accept Castro‟s assertion
that the District Court injected some confusion into the scope
of the appellate waiver through emphasis and omission during
the plea colloquy, we cannot accept that the colloquy
overcame the import that the plea agreement‟s terms must
have had for Castro, a man with years of law enforcement
experience and two post-graduate degrees. A deficient plea
colloquy will not overcome the plain terms of an appellate
waiver when the defendant is highly educated and should
accordingly be held to his informed understanding of the text
of the waiver. See Goodson, 544 F.3d at 540-41 (defendant
who was “college educated” and who had “successfully
perpetrated wire fraud and the uttering of counterfeit checks”
was held to his informed understanding of the plain terms of
the plea agreement). Castro affirmed under oath that he
understood the plea agreement, and nothing in the record
undermines that affirmation. Given the plain terms of the
plea agreement in this case, and given Castro‟s education and
professional background, we conclude that he knowingly and
voluntarily waived his right to appeal his “conviction … or
any other matter relating to this prosecution.” (App. at 127.)

3. Miscarriage of Justice

Castro‟s knowing and voluntary waiver forecloses his
appeal of the conviction on Count Three, unless the waiver
would result in a miscarriage of justice. Castro says it would,
because the record is devoid of evidence that he made a false

21
statement when he stated that he received no money from
Encarnacion in repayment of his $90,000 investment. We are
compelled to agree.

We have not previously evaluated a challenge to an
appellate waiver that is grounded on a claim of insufficiency
of evidence amounting to a miscarriage of justice. We have,
however, evaluated claims of insufficiency of evidence in the
plain error context and have explained that plain error
warranting reversal exists when the insufficiency “resulted in
a fundamental miscarriage of justice.” United States v. Barel,
939 F.2d 26, 37 (3d Cir. 1991). To determine if that exacting
standard is met, “we review the evidence in the light most
favorable to the Government and will sustain the verdict
unless a rational juror could not have found that the
Government proved” one or more elements of the offense
beyond a reasonable doubt. United States v. Williams, 299
F.3d 250, 253-54 (3d Cir. 2002). The prosecution‟s failure to
prove an essential element of the charged offense does
constitute plain error, United States v. Wolfe, 245 F.3d 257,
260-61 (3d Cir. 2001), and so can be understood as a
miscarriage of justice, see United States v. Jones, 471 F.3d
478, 480 (3d Cir. 2006) (“[A]ffirming a conviction where the
government has failed to prove each essential element of the
crime beyond a reasonable doubt affect[s] substantial rights,
and seriously impugns the fairness, integrity and public
reputation of judicial proceedings.” (internal quotation marks
omitted)).

It bears emphasis, however, that a “manifest
miscarriage of justice” warranting reversal on plain error
review occurs only where the record is “devoid of evidence
pointing to guilt” – a “stricter than usual standard.” United

22
States v. Green, 293 F.3d 886, 895 (5th Cir. 2002) (internal
quotation marks omitted); see also United States v. Vasquez,
560 F.3d 461, 469 (6th Cir. 2009) (“Because [defendant]
failed to move for a judgment of acquittal at either the close
of the government‟s case or the close of his case, we will
reverse his conviction only if the record is devoid of evidence
pointing to guilt, such that a manifest miscarriage of justice
occurred.” (internal quotation marks omitted)); United States
v. Irby, 558 F.3d 651, 653 (7th Cir. 2009) (“[R]eversal is
warranted only if the record is devoid of evidence pointing to
guilt, or if the evidence on a key element was so tenuous that
a conviction would be shocking.” (internal quotation marks
omitted)); United States v. Spinner, 152 F.3d 950, 956 (D.C.
Cir. 1998) (“[A] miscarriage [of justice] would exist only if
the record is devoid of evidence pointing to guilt, or because
the evidence on a key element of the offense was so tenuous
that a conviction would be shocking.” (alteration and internal
quotation marks omitted)).

These insights from the plain error context are
applicable to the “miscarriage of justice” argument before us
now. Cf. Hahn, 359 F.3d at 1327 (holding that for an error to
result in a miscarriage of justice that overcomes an appellate
waiver “„the error [must] seriously affect[] the fairness,
integrity or public reputation of judicial proceedings‟”
(quoting United States v. Olano, 507 U.S. 725, 732 (1993)
(alterations in original)). Castro is therefore required to show
that, when viewed in the light most favorable to the
government, the record is entirely devoid of evidence that he
committed each element of a § 1001 offense – specifically,
that he made a false statement to government officials when
he insisted that he had not received money from Encarnacion
in repayment of his $90,000 loan – so that allowing his

23
conviction to stand would “seriously impugn[] the fairness,
integrity and public reputation of judicial proceedings.”
Jones, 471 F.3d at 480 (internal quotation marks omitted).

Section 1001 calls for punishment of anyone who
“knowingly and willfully … makes any materially false,
fictitious, or fraudulent statement or representation” in any
matter within the jurisdiction of the federal government. 18
U.S.C. § 1001(a)(2).

To establish a violation of § 1001, the
government [is] required to prove each of the
following five elements: (1) that [the accused]
made a statement or representation; (2) that the
statement or representation was false; (3) that
the false statement was made knowingly and
willfully; (4) that the statement or
representation was material; and (5) that the
statement or representation was made in a
matter within the jurisdiction of the federal
government.

United States v. Moyer, 674 F.3d 192, 213 (3d Cir. 2012). It
is uncontroverted that all three payments that Castro received,
ostensibly in repayment of Encarnacion‟s “debt,” were in fact
not from Encarnacion but rather from the FBI through Moshe.
None of the money in question actually came from
Encarnacion, either directly or indirectly, nor had Castro
collected any other money from Encarnacion in repayment
for the supposed debt. Castro‟s statement that he had not
received money from Encarnacion, though intended to be a
lie, was therefore entirely true, and the government cannot
prove the second element of the offense.

24
 That fact is crucial because, to properly convict Castro
of violating § 1001, the government must be able to show that
he made a statement to government agents that was untrue,
and the government cannot satisfy that burden by showing
that the defendant intended to deceive, if in fact he told the
literal truth. In Bronston v. United States, 409 U.S. 352, 362
(1973), the Supreme Court held that a conviction under the
federal perjury statute, 18 U.S.C. § 1621, cannot rest on
testimony that is unresponsive to the interrogation, even if
intentionally deceptive, so long as the answer in question is
literally true and the questioner is free to ask further
clarifying questions. We applied Bronston in United States v.
Serafini, 167 F.3d 812, 822-24 (3d Cir. 1999), affirming the
dismissal of a charge under the “false material declarations”
statute, 18 U.S.C. § 1623, as applied to grand jury
questioning. In Serafini, we also stated that § 1001 is “[a]
close kin” to §§ 1621 and 1623. 167 F.3d at 813 n.2. Thus,
the same interpretive principles apply to § 1001 prosecutions
as were applied in Bronston and Serafini. See also United
States v. Milton, 8 F.3d 39, 45 (D.C. Cir. 1993) (“The defense
of literal truth applies to section 1001 prosecutions … .”).
Accordingly, when a statement is literally true, it is, by
definition, not false and cannot be treated as such under a
perjury-type statute, no matter what the defendant‟s
subjective state of mind might have been. Cf. Williams v.
United States, 458 U.S. 279, 284-85 (1982) (a bad check,
even when knowingly used to defraud, cannot be a “false
statement” within the meaning of 18 U.S.C. § 1014, because
as a matter of negotiable instruments law a check makes no
assertion about the truth of any matter stated thereon).

25
 Viewing the record as required by Bronston, it is
devoid of evidence that Castro made a false statement when
he told government agents that he had not received money
from Encarnacion. On the contrary, that statement was
completely, if unintentionally, accurate. Thus, allowing his
conviction on Count Three to stand would be to allow a
conviction when there has been a complete failure of proof on
an essential element of the charged crime, and that would
seriously impugn the fairness, integrity, and public reputation
of our courts. In short, such a conviction constitutes a
miscarriage of justice.

The government nevertheless argues that, given
Castro‟s belief that he was lying to FBI agents, there is
nothing unfair in his conviction. (See Appellee‟s Br. at 37
(“Castro does not contend that he was unjustly charged with
or convicted of this offense, but argues only that the evidence
was legally insufficient to support his conviction.”).) In the
broadest sense, it is surely so that Castro was morally wrong
even if not legally guilty, but our legal system does not
convict people of being bad. If they are to be convicted, it is
for specific crimes, and the government here undertook the
burden of proving that Castro had committed each element of
the specific crime set forth in § 1001. It failed to do that.

The government tries to work its way around this
failure-of-proof problem by arguing for a “sting operation
exception” in § 1001 prosecutions. As the government sees
it, whether Castro‟s statements were literally true is
irrelevant, as long as he subjectively believed he was lying to
the FBI when he made them. A contrary position, the
government argues, “would pervert the very purpose of the
literal truth defense, which is to protect people from

26
prosecution for literally true responses to the precise question
asked, and surely was not intended to protect those who
knowingly and willfully lie about their actions solely because
they unknowingly acted in collusion with a government agent
instead of a true criminal cohort.” (Appellee‟s Br. at 47.)

The ready and dispositive response to that argument is
that, even if a “sting exception” to the strictures of § 1001 is a
good idea, it is simply not in the statute. Congress knows
how to pass laws that penalize statements made to law
enforcement officers by a defendant who incorrectly believes
the statements to be false. Compare 18 U.S.C. § 1956(a)(1)
(“knowing” laundering of funds “which in fact involves the
proceeds” of a crime), with id. § 1956(a)(3) (intentional
laundering of funds “represented to be” proceeds of a crime).
But it did not do so when it enacted § 1001, and we are not
free to amend the law. Under analogous circumstances, the
United States Court of Appeals for the Second Circuit
reversed as plain error a conviction for “knowing possession”
of stolen government property because the property was not
actually “stolen” but was rather sold to the defendant by
agents in a sting operation. United States v. Golomb, 811
F.2d 787, 792-93 (2d Cir. 1987). “Knowledge and belief are
very different mental states,” the court held, and although the
defendant “may very well have believed the checks were
stolen, … [the statute] cannot be interpreted to support a
conviction when the property at issue was not stolen.” Id. at
792.

The government nevertheless insists that a jury could
conclude, based on the evidence, “that the money Castro
received came „from‟ Encarnacion.” (Appellee‟s Br. at 41.)
According to the government, “[t]he FBI paid $21,000 in real

27
cash to Castro, through its agent, Moshe, and represented
through Moshe that the payments were on behalf of
Encarnacion. A jury could thus readily determine that Castro
received money „from‟ Encarnacion, and lied about it to the
agents when asked.” (Id. at 41.) It is not clear how the
quotation marks around the word “from” in that sentence help
the argument. The money was not “from” Encarnacion in any
sense, and we are frankly at a loss to understand the
government‟s assertion that Castro “not only believed that his
answer was false … , but it was in fact false.” (Appellee‟s
Br. at 50.) There is, quite literally, no evidence whatsoever
that even a penny of the money that Moshe handed over to
Castro came from Encarnacion. To say, as the government
does, that “[t]he FBI actually gave Castro $21,000 on
Encarnacion‟s behalf” (Appellee‟s Br. at 52), is an invention,
since nothing shows that Encarnacion owed Castro anything,
much less that he authorized the government to pay Castro on
his behalf. Castro is therefore not guilty on Count Three,
because the statement set forth in that count simply was not
false.8

8
The District Court‟s jury instructions were correct in
highlighting that “[a] false … statement … is an assertion
which is untrue when made.” (D.I. 92:150-51 (Tr. 4/18/11)
(emphasis added).) The subjective belief of the person
making the statement is an entirely separate element of the
offense. The false statement must be “known by the person
making it or using it to be untrue.” (Id.) In this regard, we
note our disagreement with the government‟s assertion that
“the fact that Castro was not charged with attempting to make
a false statement is of no consequence.” (Appellee‟s Br. at
52.) What is charged is of enormous consequence, and had

28
 The complete failure of proof on the “actual falsity”
element of the offense charged in Count Three requires
reversal of Castro‟s conviction on that count, as the
conviction is infected with plain error and constitutes a
miscarriage of justice.

B. The District Court’s Denial of the
Government’s Motion for an Additional One
Point Reduction in Castro’s Offense Level for
Acceptance of Responsibility

Castro also contends that his 60-month sentence under
Count Nine is procedurally unreasonable because the District
Court erred in refusing to reduce his offense level under
§ 3E1.1(b). In his view, the additional adjustment is
mandatory if the government moves for it and the other
requirements of the provision are met. Whether that is so is a
question we have not addressed but which has divided other
circuits. Compare United States v. Williamson, 598 F.3d 227
(5th Cir. 2010) (district court has authority to determine
whether conditions for one level reduction for acceptance of
responsibility under § 3E1.1 have been satisfied), with United
States v. Mount, 675 F.3d 1052, 1055-57 (7th Cir. 2012)
(application of additional one level decrease in defendant‟s
offense level under § 3E1.1 is mandatory). We decline to
address that question, however, because it is precluded by
Castro‟s appellate waiver and no miscarriage of justice would
result from enforcing the waiver on this point.

there been an effort to charge and prove an attempt, there
would be another and very different set of legal issues in play.

29
 Castro says that his argument is not precluded by the
appellate waiver because it implicates one of the express
exceptions contained in the waiver – namely, the exception
for “constitutional claims that the relevant case law holds
cannot be waived.”9 (App. at 127.) But Castro provides no
relevant authority to demonstrate that the “constitutional
claims” exception applies in this context. It appears instead
that a district court‟s arguably erroneous calculation of a
guidelines range “is precisely the kind of „garden variety‟
claim of error contemplated by [an] appellate waiver.”
Sotirion v. United States, 617 F.3d 27, 38 (1st Cir. 2010). It
is not a “miscarriage of justice.” See Corso, 549 F.3d at 931-
32 (“[A]llow[ing] alleged errors in computing a defendant‟s
sentence to render a waiver unlawful would nullify the waiver
based on the very sort of claim it was intended to waive.”
(second alteration in original) (internal quotation marks
omitted)); United States v. Price, 558 F.3d 270, 283-84 (3d

9
Castro does not claim, as he did when arguing that
his conviction under Count Three was not covered by the
appellate waiver provision, that the District Court‟s plea
colloquy injected uncertainty into the meaning of the
otherwise plain terms of the appellate waiver. Nor could he.
A review of the plea colloquy establishes that the District
Court properly questioned Castro and took affirmative steps
to ensure that his plea was knowing and voluntary.
Specifically, Castro testified that he had read the terms of the
plea agreement, that he had discussed them with his attorney,
that he agreed to all of the terms, and that he understood that
the agreement limited his right to appeal. Castro‟s plea was
thus knowing and voluntary with respect to the District
Court‟s denial of the government‟s motion for a one-level
reduction in Castro‟s offense level pursuant to § 3E1.1(b).

30
Cir. 2009) (holding enforcement of an appellate waiver would
not constitute a miscarriage of justice despite defendant‟s
claim that the government abused its discretion by not
requesting an additional reduction in the district court‟s
sentencing calculation); United States v. Mabry, 536 F.3d
231, 243 (3d Cir. 2008) (defendant‟s challenges to district
court‟s sentencing calculation were “insubstantial and clearly
encompassed by the broad waiver,” and “[did] not implicate
fundamental rights or constitutional principles”).

Castro has failed to demonstrate that his appellate
waiver does not encompass this claim or that he did not waive
it knowingly and voluntarily, and he has not established that
enforcement of the appellate waiver would result in a
miscarriage of justice. We thus decline to exercise
jurisdiction over his appeal with respect to the District
Court‟s rejection of the government‟s motion for a downward
departure under § 3E1.1(b).

C. The Procedural and Substantive
Reasonableness of Castro’s 60-Month Sentence
Under Count Nine

Finally, Castro argues that, when it imposed a sentence
that varied upwards by nearly 50 percent above the highest
sentence recommended by the guidelines, the District Court
produced a sentence that was procedurally and substantively
unreasonable. According to Castro, the Court did not
adequately explain why such a harsh sentence was necessary
to achieve the legitimate aims of sentencing, considering all
the aggravating and mitigating factors of the case, and the
Court did not adequately account for Castro‟s lengthy record

31
of good works.10 In response, the government supports the
sentence as well justified in light of numerous statements by
the District Court explaining the reasons for the sentence
given. We agree that the sentence was well explained, but,
given the flawed inclusion of Count Three in the sentencing
calculus, the overall sentence must be reassessed.

Despite our well-known procedure for reviewing
criminal sentences,11 the District Court‟s upward variance is

10
Castro‟s arguments in this regard are not foreclosed
by his appellate waiver because the waiver contains an
exception for “claims that … the sentencing judge, exercising
the Court‟s discretion pursuant to United States v. Booker,
543 U.S. 220 (2005), imposed an unreasonable sentence
above the final Sentencing Guideline range.” (App. at 128.)
11
Our review of a criminal sentence “proceeds in two
stages.” United States v. Tomko, 562 F.3d 558, 567 (3d Cir.
2009) (en banc). First, we review the sentence for procedural
error, “such as failing to calculate (or improperly calculating)
the Guidelines range, treating the Guidelines as mandatory,
failing to consider the § 3553(a) factors, selecting a sentence
based on clearly erroneous facts, or failing to adequately
explain the chosen sentence – including an explanation for
any deviation from the Guidelines range.” Gall v. United
States, 552 U.S. 38, 51 (2007). If there was procedural error,
“our preferred course is to remand the case for re-sentencing,
without going any further.” United States v. Merced, 603
F.3d 203, 214 (3d Cir. 2010). Second, if there was no
procedural error, “we review for substantive reasonableness,
and „we will affirm [the sentence] unless no reasonable
sentencing court would have imposed the same sentence on
that particular defendant for the reasons the district court

32
unreviewable at this juncture, because, in calculating Castro‟s
“combined offense level” for “multiple counts” using the
method supplied by § 3D1.4 of the sentencing guidelines, the
Court arrived at an offense level that was one level higher (20
instead of 19) than would have resulted if the conviction on
Count Three had not been included. That in turn led to a
guidelines range of 33 to 41 months instead of 30 to 37
months. “[G]iven the importance of a correct Guidelines
calculation both to the sentencing process that district courts
are required to conduct and to our ability to carry out
reasonableness review, the use of an erroneous Guidelines
range will typically require reversal under 18 U.S.C.
§ 3742(f).” United States v. Langford, 516 F.3d 205, 215 (3d
Cir. 2008). Our reversal of Castro‟s conviction under Count
Three accordingly necessitates a remand for resentencing
solely for Castro‟s guilty plea on Count Nine. See id. at 211,
214 (“[A] correctly calculated Guidelines range will often be
a necessary precondition of our reasonableness review.
Where a district court begins with an erroneous range, it will
be difficult for us to determine that it fulfilled its duty to
consider the Guidelines and reason through to the ultimate
sentence,” because “the correct computation of the Guidelines
range and any departures therefrom serves to clarify the basis
for the sentence imposed and thus facilitates reasonableness
review.”).

We note with appreciation the District Court‟s
thorough and thoughtful accounting of the aggravating and

provided.‟” United States v. Negroni, 638 F.3d 434, 443 (3d
Cir. 2011) (quoting Tomko, 562 F.3d at 568). At both stages
we review for abuse of discretion. United States v. Wise, 515
F.3d 207, 217-18 (3d Cir. 2008).

33
mitigating circumstances in this case and its explanation for
why it concluded that an upward variance was necessary to
accomplish the legitimate aims of sentencing.12 Despite that
exemplary handling of the always difficult work of crafting
and explaining an appropriate sentence, we must nevertheless
remand for resentencing because we cannot conclude with
confidence that, had the District Court operated from the

12
For example, the Court specifically acknowledged
much of Castro‟s good character, including that, “[w]ith
perhaps one or two exceptions, I have never received as many
letters attesting to a defendant‟s good character and urging
leniency as I have in this case,” which showed that, “[c]learly,
he has the support and respect of many people in this
community and elsewhere.” (App. at 225.) The Court also
recognized that Castro “has shown contrition for what he has
done” and “is sincere in saying that he is sorry.” (App. at
228.) Despite Castro‟s “many good works, particularly with
children” (App. at 225), the Court expressed deep concern
over Castro‟s willingness to use “force and violence.” (App.
at 227; see also id. (“I can‟t emphasize this enough, if force
and violence had been used, someone could have been
killed.”).) But “most troubling” to the Court was that Castro
was a police officer, and police officers “are held to a much
higher standard.” (App. at 230.) The Court felt “a
compelling need to afford adequate deterrence to criminal
conduct, particularly to deter others in law enforcement who
may contemplate illegal conduct.” (App. at 229.) After
considering the mitigating and aggravating evidence, the
Court found that the nature of Castro‟s conduct and the
tremendous damage caused by that conduct outweighed the
positive aspects of Castro‟s history and character, and called
for a higher sentence.

34
correct guidelines range (30 to 37 months instead of 33 to 41
months), it would still have given a 60-month sentence. See
Langford, 516 F.3d at 215 (“[T]he improper calculation of the
Guidelines range can rarely be shown not to affect the
sentence imposed.” (internal quotation marks omitted)).

On remand, the District Court is “free to make its own
reasonable application of the § 3553(a) factors” and
ultimately may choose “to reject (after due consideration) the
advice of the Guidelines” and impose the same sentence.
Kimbrough v. United States, 552 U.S. 85, 113 (2007) (Scalia,
J., concurring). But it must consider the correct guidelines
range.

III. Conclusion

For the foregoing reasons, we will reverse Castro‟s
conviction and 18-month sentence after trial on Count Three
and remand to the District Court for entry of a judgment of
acquittal on that count. We will also vacate Castro‟s 60-
month sentence under Count Nine and remand to the District
Court for resentencing on that count, using the correct
guidelines range.

35