United States v. Santiago

United States Court of Appeals
For the First Circuit

No. 13-1146
UNITED STATES,

Appellee,

v.

JUAN JOSÉ SANTIAGO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO

[Hon. Daniel R. Domínguez, U.S. District Judge]

Before

Torruella, Baldock,* and Thompson,
Circuit Judges.

Liza L. Rosado-Rodríguez, Research and Writing Specialist,
with whom Héctor E. Guzmán-Silva, Federal Public Defender, and
Héctor L. Ramos Vega, Assistant Federal Public Defender, were on
brief, for appellant.
Juan Carlos Reyes-Ramos, Assistant United States Attorney,
with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, and
Nelson Pérez-Sosa, Assistant United States Attorney, Chief,
Appellate Division were on brief, for appellee.

September 12, 2014

*
Of the Tenth Circuit, sitting by designation.
 THOMPSON, Circuit Judge. Defendant Juan José Santiago

was sentenced to twelve months in prison and ten years supervised

release after pleading guilty to one count of failing to register

as a sex offender. The terms of Santiago's supervised release

included a series of special sex offender conditions, which he now

seeks to vacate. There is merit to some, but not all, of

Santiago's claims of error. In short, while a waiver of appeal

serves to defeat the bulk of Santiago's challenges, we vacate one

of the conditions of supervised release, which was imposed in

Santiago's absence.

I. The Start of Things

Santiago's story, inasmuch as it is relevant to this

appeal, begins over a decade ago in Florida. On March 19, 2002, a

Mulberry, Florida police detective responded to a hospital

emergency room for the reported rape of a seven-year-old girl. The

girl's mother, who was Santiago's girlfriend at the time, told the

detective that the girl had said that "her daddy," referring to

Santiago, "had touched her privates."1 Two days later, the girl

was interviewed by the Florida Department of Health's Child

Protection Team. She told them that "her daddy would take her and

his pants off, would get on top of her and move around like in the

movies she had seen with him" and that "he touched and licked her

1
In her statements, the girl refers to Santiago as daddy,
though the record contains no indication that he is her biological
father, nor that Santiago and her mother were ever married.

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privates." Santiago's girlfriend confirmed that there were two

pornographic videos in the couple's night stand and consented to a

search, which turned up both videos. Santiago was arrested.

Santiago was charged, under Florida law, with one count

of sexual battery on a person less than twelve years of age, and

one count of lewd molestation. The sexual battery charge was later

reduced to child abuse. Santiago pleaded nolo contendre to both

the lewd molestation and the child abuse charge. On July 19, 2002,

Santiago was sentenced to five years of probation for the child

abuse charge, and ten years of probation for the lewd molestation

charge, to be served concurrently. Pursuant to the Sex Offender

Registration and Notification Act (SORNA), 18 U.S.C. § 16913,

Santiago was required to register as a sex offender, and keep his

registration current, in all jurisdictions where he resided.

Over the next couple of years, Santiago repeatedly had

trouble abiding by the terms of his probation. First, in July

2003, Santiago missed his court ordered curfew; an arrest warrant

was issued, but later withdrawn. A year or so later, in September

2004, Santiago moved from his approved residence to another

residence without prior permission from his probation officer, and

failed to pay his monthly cost of supervision. Santiago admitted

to the violations, and served forty-five days in county jail. Upon

release, his probation was restored.

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 The stint in county jail did little to improve Santiago's

compliance. Shortly after his release, in November 2004, an arrest

warrant issued because Santiago had failed to register as a sex

offender, neglected to report to the probation office, and had not

paid court costs. A few weeks later, Santiago's probation officer

reported additional violations: Santiago had once again moved from

his approved residence without prior approval, had failed to

successfully complete his sex offender treatment program, and had

failed to pay court costs and restitution.

Having exhausted the system's goodwill, Santiago had his

probation revoked on August 11, 2005. He was sentenced to just

over seven years in Florida state prison for the child abuse

charge, and five years for the lewd molestation charge, to be

served concurrently. Santiago was released from prison on November

21, 2010. At some point following his release, Santiago moved from

Florida to Puerto Rico.

II. The Instant Offense

Once in Puerto Rico, Santiago again failed to register as

a sex offender. Law enforcement caught up with him and, on April

3, 2012, a federal grand jury indicted Santiago on one count of

violating 18 U.S.C. § 2250 for traveling through interstate

commerce and knowingly failing to register with Puerto Rico

authorities as required by SORNA.

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 Santiago decided to work with the government and he

entered into a plea agreement. The agreement indicated that the

Sentencing Guidelines yielded a recommended sentence of twelve to

eighteen months, and that the government, in exchange for a guilty

plea, would be satisfied with the bottom end of that range. The

agreement also noted that the penalty for the offense charged

included a term of supervised release that could range from five

years to life. Pertinent to our purposes, the plea agreement

contained a waiver of appeal provision, which provided that should

the court accept the agreement and sentence Santiago according to

its terms, Santiago would be "waiv[ing] and permanently

surrender[ing] his right to appeal the judgment and sentence in

this case."

At the change of plea hearing, the magistrate judge

explained to Santiago the implications of the plea agreement,

including the fact that Santiago would be giving up his right to

appeal the judgment and sentence. She also explained the penalties

he faced, noting the applicable term of supervised release and the

fact that Santiago's release would be subject to some conditions.

Santiago confirmed that he understood, and his attorney vouched for

Santiago's competence to enter into the plea agreement. The court

accepted Santiago's guilty plea; only sentencing considerations

remained.

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 On December 6, 2012, the probation office issued its

presentence investigation report (PSR). The PSR recommended (in

addition to less relevant things) that a variety of special sex

offender conditions be imposed, which generally speaking placed

limitations on Santiago's contact with minors and required sex

offender treatment with compliance monitoring.

Santiago's sentencing hearing took place on January 4,

2013. After some skirmishing not relevant to this appeal, the

district court judge sentenced Santiago to twelve months in prison

followed by a ten-year term of supervised release. In accord with

the PSR's recommendation, the judge, at the hearing, imposed a

number of special sex offender conditions as terms of Santiago's

supervised release. The court inflicted the conditions over the

objection of Santiago's attorney, who argued that the record was

bereft of any justification for such conditions.2 The judge

disagreed, finding the fact that Santiago had pleaded nolo

contendre to lewd molestation of his then-girlfriend's daughter in

2002 sufficient to warrant the special conditions.

The court issued its written judgment the same day as the

sentencing hearing. In addition to the special sex offender

2
The government, for its part, was ambivalent at first,
stating a preference for leaving the issue of the special
conditions up to the court's discretion. When pressed by the
sentencing judge, the government attorney stated that the
government did not think special sex offender conditions needed to
be imposed at that time.

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conditions announced at the hearing, the judgment contained one

additional condition, numbered thirteen in the judgment, which

provided that Santiago could not use or possess sexually explicit

material or frequent any establishments providing pornography or

sexual services.

III. This Appeal

Santiago comes to us with a circumscribed advancement.

He does not challenge his sentence, his term of supervised release,

or the general conditions of that release. Rather he solely takes

issue with some of the special sex offender conditions imposed by

the district court.

First, he claims that a handful of the conditions were

unwarranted because they were not reasonably related to his failure

to register (which is not a sex offense) or any of the overarching

goals of supervised release. The disputed conditions can be

summarized as follows. Santiago must: (1) have no unapproved

contact via mail, phone, or electronically with minors; (2) undergo

sex offender evaluation and treatment; (3) avoid entering,

loitering, or working near any areas frequented by minors without

probation's approval; (4) not live near any area frequented by

minors; and finally (5) refrain from living with minors unless

probation gives the okay.3 Next, Santiago argues that condition

3
At his sentencing hearing, Santiago was particularly
concerned with the conditions that prohibited him from living with,
or coming in contact with, minors because at the time he had

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thirteen of the judgment (recall this was the condition relating to

sexually explicit materials and establishments), in addition to not

being justified, was in violation of his right to be present

because it was not announced at his sentencing hearing.

The government does not think we need to reach the merits

of either claim. It retorts that pursuant to the waiver of appeal

provision in his plea agreement, Santiago gave up his right to

appeal his sentence, including the special terms of his supervised

release.

The multiple special sex offender conditions that

Santiago claims were baseless given the circumstances, and the

unannounced condition thirteen, suggest distinctive concerns. And

ultimately they require different results. As such, we take them

independently.

IV. The Supposed Unwarranted Conditions

With respect to the conditions Santiago claims were

groundless, our inquiry, as the government suggests, starts and

ends with the waiver of appeal contained in Santiago's plea

agreement. Santiago does not dispute that because he was sentenced

in accordance with the plea agreement he is precluded by the waiver

from appealing his term of imprisonment. Rather, he attempts to

draw a distinction between the twelve-month prison term and his

several minor children in his family, including a child of his own
and his girlfriend's children.

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supervised release conditions. Because, he says, the plea

agreement was silent as to which conditions of supervision were to

be imposed, and it did not make any recommendation one way or the

other, the conditions fall outside the waiver's scope. Our

jurisprudence is at odds with Santiago's position.

The waiver at issue here explicitly stated that Santiago

was giving up "his right to appeal the judgment and sentence in

this case." (Emphasis added.) Significantly, a supervised release

term is part of a sentence. See United States v. Brown, 235 F.3d

2, 4 (1st Cir. 2000) (providing that a "supervised release term is

an integral part of a sentence" and that a defendant can rarely

claim unfair surprise when the resultant conditions of supervised

release are imposed); United States v. Mandarelli, 982 F.2d 11, 12

(1st Cir. 1992) (Breyer, J.) ("Supervised release is part of a

prison sentence, to be served after imprisonment.") (internal

quotation marks omitted) (emphasis in original); 18 U.S.C. § 3583

("The court, in imposing a sentence to a term of imprisonment for

a felony or a misdemeanor, may include as part of the sentence a

requirement that the defendant be placed on a term of supervised

release.").

Consistent with this prescript, we have routinely applied

appellate waivers to preclude defendants from appealing their

conditions of supervised release, where the waiver extended to the

defendant's power to appeal the judgment and sentence. See United

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States v. Rodríguez-Santana, 554 F.App'x. 23, 26 (1st Cir. 2014)

(defendant could not appeal special sex offender conditions in

light of appellate waiver); United States v. Rivera-López, 736 F.3d

633, 637 (1st Cir. 2013)(waiver of appeal precluded this court from

reviewing defendant's nightly curfew and electronic monitoring

conditions); United States v. Nguyen, 618 F.3d 72, 76 (1st Cir.

2010) (finding appellate review of a drug testing condition

foreclosed by a waiver of appeal). As we said in Rodríguez-

Santana, while addressing special sex offender conditions not

unlike the ones Santiago challenges here, "'[a] supervised release

term is an integral part of a sentence' generally encompassed

within any broadly-worded agreement not to appeal a 'sentence.'"

554 F.App'x at 25 (quoting Brown, 235 F.3d at 4).

Given all this, we have no trouble concluding that the

word "sentence" in Santiago's waiver encompasses every component of

the sentence, including the term of supervised release and its

attendant conditions, thus bringing the instant action within the

waiver's reach. Having established the waiver's scope does not,

however, bring things to an end. The question of enforcement of

the waiver remains. The general rule is that when knowing and

voluntary, an appellate waiver is generally enforceable, absent an

indication that the waiver would work a miscarriage of justice.

Rivera-López,736 F.3d at 635; United States v. Teeter, 257 F.3d

14, 24-26 (1st Cir. 2001).

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 To assess how well-informed Santiago's waiver was we look

to the plea agreement and the change-of-plea colloquy. See Teeter,

257 F.3d at 24. The plea agreement contained a clearly worded

"waiver of appeal," which explicitly stated that Santiago was

giving up his right to appeal the judgment and sentence should the

court accept, and sentence him in accord with, the plea agreement.

The plea agreement set forth both the potential term of

incarceration, and the term of supervised release, faced by

Santiago. At the change of plea hearing, the magistrate judge

clearly explained to Santiago the implications of his entering into

this agreement. She articulated the maximum penalties for the

crime, including the applicable term of supervised release, and

then explained that this term would be subject to "some

conditions," and that, should Santiago violate those conditions, he

would "go back to jail for the full term." Santiago confirmed

that he understood. The judge also informed Santiago that, by

virtue of the waiver of appeal provision, he was "giv[ing] up [his]

right to appeal both the judgment and . . . sentence." Again,

Santiago understood. Santiago's attorney indicated that she had

gone over the plea agreement with him, including the rights he

would be relinquishing. She described their conversations as

"above-average" and "intelligent." The magistrate judge found, and

Santiago's attorney confirmed, that Santiago was competent to enter

the plea.

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 Taking into consideration the exchange at the change of

plea hearing and the language of the waiver itself, it is apparent

that Santiago's relinquishing of his appellate rights was knowing

and voluntary. The waiver of appeal itself was unambiguous and the

judge sufficiently called the waiver to Santiago's attention while

making sure he understood its ramifications. The fact that the

plea agreement does not specify Santiago's conditions of supervised

release is inconsequential; a defendant need only understand how

the right he is giving up would likely apply in the general sense,

rather than the specific consequences of invoking it. See

Rodríguez-Santana, 554 F.App'x at 25 (citing United States v. Ruiz,

536 U.S. 622, 629 (2002)).

That leaves Santiago with just one more shot at

sidestepping the waiver of appeal. And it is not a task easily

accomplished. In our "sound discretion," we may refuse to honor

the appellate waiver if denying Santiago a right of appeal would

result in a "miscarriage of justice." Teeter, 257 F.3d at 25.

This "exception is meant only for 'egregious cases' and is to be

applied 'sparingly and without undue generosity.'" Sotirion v.

United States, 617 F.3d 27, 36 (1st Cir. 2010)(quoting Teeter, 257

F.3d at 25, 26).

Aware (by his own admission) of the difficulty of

establishing a miscarriage of justice, Santiago devotes little time

to this issue on appeal. He only argues that "it would be

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unreasonable to expect him to anticipate special conditions at the

time he waived his right to appeal" because he "was not warned by

the district court of the possibility of receiving harsh sex

offender conditions of supervised release." This offering falls

short. To successfully invoke the miscarriage of justice

exception, a "garden-variety error will not suffice," rather there

must be, "at a bare minimum, an increment of error more glaring

than routine reversible error." United States v. Chambers, 710

F.3d 23, 31 (1st Cir. 2013) (internal quotation marks omitted). No

such error - garden variety or otherwise - invaded the proceedings

here.

"Under ordinary circumstances, the district court has

significant discretion in formulating conditions of supervised

release." Nguyen, 618 F.3d at 76. The conditions must just be

reasonably related to one or more of the goals of supervised

release, i.e., the nature and circumstances of the offense and the

history and characteristics of the defendant, the need to deter

criminal conduct, the need to protect the public, and the needed

training, care, or treatment of the defendant. See Rivera-López,

736 F.3d at 635 (citing U.S.S.G. § 5D1.3(b); 18 U.S.C. 3583(d)).

At the same time, the conditions must "involve[] no greater

deprivation of liberty than is reasonably necessary." 18 U.S.C. §

3583(d)(2). With respect to conditions of supervised release, the

"hallmark" that separates the permissible from the impermissible is

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whether, given the facts, a certain restriction was "clearly

unnecessary." Brown, 235 F.3d at 7.

While the conditions imposed on Santiago were undoubtedly

stringent, especially since the underlying offense was not a sexual

one, the conditions were not so obviously unwarranted as to

constitute a miscarriage of justice. Santiago plead nolo contendre

to lewd molestation in 2002. Since then, he violated the terms of

his probation several times, and, in violation of SORNA, failed to

register as a sex offender in two jurisdictions. At the time the

court imposed the disputed conditions, Santiago's living

arrangements mirrored those from when the 2002 offense occurred, in

that he was living in a home with his girlfriend and her minor

children. Couple this fact with Santiago's apparent inability to

abide by (or blatant disregard of) the terms of his probation, his

failure to register as a sex offender on more than one occasion,

and the well-recognized high recidivism rate for sex offenders, see

Smith v. Doe, 538 U.S. 84, 103 (2003); United States v. Sebastian,

612 F.3d 47, 51 (1st Cir. 2010), the district court's determination

that special sex offender conditions were necessary to further the

goals of supervised release (most fitting, the protection of the

public) was hardly unsubstantiated.

Nor are we persuaded by Santiago's avowal that it was

unforeseeable to him that special sex offender conditions might be

imposed. Santiago was well aware of his criminal past, his

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subsequent probation violations, and his inattention to his sex

offender registration requirements. Had Santiago wanted more of an

indication as to whether special conditions related to his status

as a sex offender might be imposed, he could have requested the

PSR, which ultimately recommended a number of such conditions,

prior to entering a guilty plea. See United States v. Donath, 616

F.3d 80, 84-85 (1st Cir. 2010) (noting, in connection with a

finding that no miscarriage of justice occurred, that the defendant

could have requested a PSR prior to waiving his right to appeal in

order to assess how his past convictions would be treated).

Whether Santiago's special sex offender conditions would

stand firm against scrutiny on direct appeal is not something we

need to get into. We need only answer "the much simpler question

of whether the conditions are so clearly erroneous and

unsubstantiated as to work a miscarriage of justice." Rivera-

López, 736 F.3d at 637. Because they are not, Santiago must be

held to his waiver of appeal as to those conditions. Condition

thirteen is a different story.

V. Condition Thirteen

To remind the reader, condition thirteen of the judgment

(generally speaking) required Santiago to refrain from using

sexually explicit material, or frequenting establishments providing

pornography or sexual services. How the condition was imposed is

important. Condition thirteen, unlike all the other special sex

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offender conditions, was not announced by the judge at Santiago's

sentencing hearing. Instead it made its first appearance in the

written judgment. Because of this, Santiago claims his right to be

present at sentencing was violated. Off the bat we need to

consider how the manner in which the condition was inflicted

impacts the applicability of Santiago's waiver of appeal.

It is well settled that a criminal defendant, by virtue

of the United States Constitution and Federal Rules of Criminal

Procedure, enjoys the right to be present at his own sentencing.

United States v. Bryant, 643 F.3d 28, 32 (1st Cir. 2011); United

States v. Sepúlveda-Contreras, 466 F.3d 166, 169 (1st Cir. 2006).

Obviously, with respect to condition thirteen, that tenet was not

complied with. As explained above, it is within our choosing to

refuse to honor an appellate waiver if doing so would result in a

"miscarriage of justice." Teeter, 257 F.3d at 25. Miscarriage of

justice is "more a concept than a constant" and the circumstances

that will justify invoking it are "infinitely variable." Id. at

25, n.9; 26. Such factors may or may not be related to the waiver

itself, Nguyen, 618 F.3d at 75, and could include "the clarity of

the error, its gravity, its character . . . 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." Teeter, 257 F.3d at 26.

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 Relief under the miscarriage of justice exception is

often sought but seldom meted out. That being said, we think this

case is more the exception than the norm and enforcing Santiago's

waiver as to condition thirteen would work a miscarriage of

justice. First, the error here is clear. Supervised release

conditions not announced at sentencing should not make a surprise

appearance in the written judgment. See, e.g., Sepúlveda-

Contreras, 466 F.3d at 169; United States v. Vega-Ortiz, 425 F.3d

20, 22 (1st Cir. 2005). Further, the error has significance, most

notably its constitutional dimensions. See, e.g., Teeter, 257 F.3d

at 25, n.9 (citing an appellant's claim that his sentence was based

on a constitutionally impermissible factor as an example of a case

where the court might set aside a waiver). The impact on Santiago

is apparent. He had a restrictive condition imposed without the

opportunity to argue that it was not warranted, and there is no

claim that he acquiesced to this result. Finally, we see little

prejudice to the government should we take up the merits of

Santiago's (very limited) appeal given that the government fully

briefed this issue.

That stumbling block out of the way, we move on to the

merits. We review Santiago's claim for harmless error. See

Sepúlveda-Contreras, 466 F.3d at 170; United States v. Ortiz-

Torres, 449 F.3d 61, 74 (1st Cir. 2006). In the case of right-to-

be-present challenges based on a sentencing court's inclusion of

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conditions of supervised release in the judgment that were not

announced at sentencing, the oral conditions control where those

conditions "conflict in a material way" with the conditions that

ended up in the judgment. Sepúlveda-Contreras, 466 F.3d at 169.

There will be no material conflict "where the defendant is on

notice that he is subject to the terms included in the written

judgment." Ortiz-Torres, 449 F.3d at 74.

The government concedes that because condition thirteen

was a non-mandatory, non-standard condition, Santiago is not

presumed to have been on constructive notice of the condition. See

Sepúlveda-Contreras, 466 F.3d at 169-70 (explaining that

"[d]efendants are deemed to be on constructive notice for mandatory

and standard conditions"). Nonetheless, the government insists we

should find that Santiago was in fact on constructive notice that

condition thirteen would be imposed given that his victim from the

2002 offense alleged that she and Santiago watched pornography

together and two pornographic videos were recovered by police. We

are not persuaded.

Here, there is clearly a conflict between the terms of

supervised release issued orally by the judge, and those contained

in the written judgment. Moreover, there is no evidence that

Santiago was on notice that a term of supervised release akin to

condition thirteen would be imposed. Unlike the other special sex

offender conditions, condition thirteen was not recommended in the

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PSR. And we disagree with the government that the fact that

pornography viewing was reported by his minor victim in 2002 should

have put Santiago on constructive notice that he would be precluded

from using or possessing sexually explicit material or frequenting

providers of such material in 2013. We conclude that the court

erred in imposing condition thirteen for the first time in the

written judgment; the question remains whether the error was

harmless.

Since the error alleged is a constitutional one, "the

government has the burden of proving beyond a reasonable doubt that

the error did not affect the defendant's substantial rights." Id.

at 171. In the context of Santiago's case, this means the

government must establish that Santiago's ability to object was not

compromised, that is, the condition would have been imposed even if

he was present. See id. at 171-72. The government has not done

this. All it did was point us to the fact that the district court

judge was unconvinced by Santiago's attorney's argument at the

sentencing hearing that the announced special sex offender

conditions were unwarranted. This brief colloquy between the judge

and the attorney does not leave us convinced beyond a reasonable

doubt that condition thirteen would have been imposed had Santiago

been given the opportunity to object. Consequently, we must vacate

condition thirteen.

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 VI. Conclusion

Because Santiago waived his right to appeal all of the

special sex offender conditions of supervised release, save

condition thirteen, we dismiss that portion of the appeal.

Condition thirteen, however, cannot stand. It is vacated and we

remand to the district court for re-sentencing consistent with this

opinion.

DISMISSED IN PART, VACATED IN PART, AND REMANDED.

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