United States of America v. Elia V. Orlando

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 15-2092
U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.
ELIA V. O RLANDO,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Eastern District of Wisconsin
No. 13-CR-208 — Rudolph T. Randa, Judge.
____________________
A RGUED J ANUARY 21, 2016 — DECIDED M AY 25, 2016
____________________
Before POSNER , EASTERBROOK, and K ANNE, Circuit Judges.
K ANNE, Circuit Judge. Defendant Elia Orlando was indict-
ed on charges of producing and possessing child pornogra-
phy in October 2013. Orlando agreed to plead guilty to mul-
tiple counts of producing child pornography in April 2014 in
exchange for the government’s sentencing recommendation
amongst other considerations. That decision set in motion
the complex process of sentencing Orlando, a process that
has already involved two sentencings and one appeal.

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2 No. 15-2092
Orlando and the government now seek a third sentenc-
ing for him. According to Orlando and the government, the
district court erred in interpreting our remand order after
the first appeal and failed to conduct a full resentencing of
Orlando. On remand, the district court only addressed Or-
lando’s term and conditions of supervised release. Orlando
also argues that the district court committed procedural er-
ror in its resentencing and that the government breached its
plea agreement by failing to recommend a term of impris-
onment of 35 years.
Finding that the district court did in fact err in interpret-
ing our remand order, we vacate Orlando’s sentence and re-
mand for a full resentencing. We do not, however, find that
the government breached its plea agreement and therefore
decline to reassign Orlando’s case to a different judge.
I. BACKGROUND
The facts and procedural posture of this case, like many
of the appeals involving the imposition of terms and condi-
tions of supervised release, are complicated. We start with
the offense that brought Orlando into federal custody before
recounting his sentencing, first appeal, and resentencing.
A. Indictment, Guilty Plea, and First Sentencing
On August 4, 2013, Milwaukee Police officers retrieved a
cell phone belonging to Orlando. The phone had been dis-
covered three days earlier by a woman in a suburban Mil-
waukee gas station. She picked up the phone after a man left
it on the checkout counter. She attempted to return the
phone to the man but was unsuccessful. The woman later
went through the phone on August 4 in an effort to locate a
number for its owner. In the process, she discovered images

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No. 15-2092 3
she believed to be child pornography and reported her dis-
covery to Milwaukee police.
The officers observed the images and then determined
the phone was owned by Orlando. That same day, police
went to Orlando’s home and arrested him. When first ques-
tioned, Orlando invoked his right to counsel. Later, however,
he changed his mind and decided to talk with police.
Orlando admitted to owning the cell phone and pos-
sessing “child porn” images—both on his phone and his lap-
top computer. Orlando allowed police to retrieve a computer
from his home and consented to a search of that computer
and his phone. Police later recovered child pornography im-
ages produced by Orlando during a forensic examination of
his cell phone.
On October 22, 2013, a federal grand jury returned an in-
dictment against Orlando in which it charged him with two
counts of production of child pornography in violation of 18
U.S.C. § 2251(a) and one count of possession of child por-
nography in violation of 18 U.S.C. § 2252(a)(4)(B). Just over a
month later, a superseding indictment was returned, which
included the same counts as the earlier indictment and add-
ed four more counts for production of child pornography.
The government and Orlando then entered into a plea
agreement. The agreement called for Orlando to plead guilty
to four counts of production of child pornography. In ex-
change, the government would drop the remaining three
counts of the superseding indictment and, according to par-
agraph 22 of the agreement, the government would “rec-
ommend a term of imprisonment of thirty-five years, fol-
lowed by a term of lifetime supervision.”

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4 No. 15-2092
Orlando fulfilled his end of the bargain on April 23, 2014,
and entered a plea of guilty to four counts of production of
child pornography. The government did the same at Orlan-
do’s August 18, 2014, sentencing. There, the government
moved to drop the three remaining counts from the super-
seding indictment and stated the following: “the Govern-
ment is making a recommendation of a term of imprison-
ment of 35 years, followed by lifetime supervision.”
The district court, however, decided to impose a sentence
of 40 years in prison followed by a life term of supervised
release, which included mandatory and discretionary condi-
tions of supervision. In imposing the conditions of super-
vised release, the district court did not evaluate or discuss
the sentencing factors from 18 U.S.C. § 3583(d), including
determining whether each discretionary condition was “rea-
sonably related” to the factors in 18 U.S.C. § 3553(a)(1),
(a)(2)(B), (a)(2)(C), and (a)(2)(D). With respect to the length
of the supervised release, the district court stated: “I'm going
to place you on supervised release for life, which I must do.”
The district court also did not inform Orlando of the “Stand-
ard Conditions of Supervision” that were imposed in the
judgment. 1
1 The phrase “standard conditions” can have two meanings in a sentenc-
ing context. The sentencing guidelines provide for fifteen “standard”
conditions that are “recommended for supervised release.” U.S.S.G.
§ 5D1.3(c). The administrative office for the U.S. Courts provides thirteen
“Standard Conditions of Supervision” in form number AO 245B, “Judg-
ment in a Criminal Case.” The thirteen conditions are substantially the
same as the first thirteen conditions provided in U.S.S.G. § 5D1.3(c). In
this case, the district court imposed the thirteen “Standard Conditions of
Supervision” from Form AO 245B. It should be noted that although these
(continued…)

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No. 15-2092 5
B. First Appeal
Orlando appealed and challenged his term of supervised
release and the conditions of that supervised release. Instead
of filing a response, the government filed a joint motion with
Orlando on February 24, 2015, in which both sought an or-
der from this court “summarily revers[ing] the judgment of
the district court and to remand the case for resentencing,
consistent with” United States v. Thompson, 777 F.3d 368 (7th
Cir. 2015). According to the motion, the district court did not
make the required findings before imposing supervised re-
lease conditions, failed to state the “standard conditions of
supervised release” at sentencing, and mistakenly believed
the imposition of lifetime supervision was required.
We granted the joint motion, vacated Orlando’s sentence,
and remanded to the district court “for resentencing in light
of” Thompson on March 5, 2015.
C. Resentencing
On May 13, 2015, Orlando appeared via video conference
before the district court for a resentencing hearing. At the
hearing, the district court stated the following:
The case is remanded to this Court pursuant to a
Seventh Circuit Court order which asks the Court
(…continued)
conditions are called “standard,” the imposition of these conditions by a
district court is not mandatory like those required by 18 U.S.C. § 3583(d).
Therefore, the imposition of these “standard” conditions is discretionary
because the court must still make adequate findings before imposing
them. See United States v. Kappes, 782 F.3d 828, 848 (7th Cir. 2015); United
States v. Thompson, 777 F.3d 368, 376–78 (7th Cir. 2015).

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6 No. 15-2092
to reimpose—or revisit certain conditions of super-
vised release, and the Court’s failure to formally
calculate the guidelines range. The Court’s treat-
ment of the guidelines recommended a life term of
supervised release as mandatory. So that’s what
we’re here to discuss.
(Orlando Sent. Tr. 2, May 13, 2015.) Neither Orlando nor the
government disputed the district court’s characterization of
the purpose for sentencing. Instead, the government and Or-
lando presented their agreement to ask the court for a delay
in imposing discretionary conditions of supervised release,
until Orlando was “closer to the release date from his term
of imprisonment.” Id. at 3. The district court obliged, though
it went further than the government and Orlando requested.
The district court delayed the imposition of any conditions
of supervised release—mandatory or discretionary—as well
as the term of supervised release until “the Defendant’s re-
leased from custody.” Id. at 4.
After resolving the issues related to supervised release,
the district court said “[t]hat satisfies, I believe, the remand
order from the Seventh Circuit” and then asked if there were
any other matters to discuss. Orlando, through his attorney,
responded by asking if the district court would consider im-
posing a different term of imprisonment. Id. His attorney,
however, immediately followed that request with the follow-
ing statement:
I told him that it looked like the remand order may
have precluded that, but it is a re-sentencing. So I
did discuss with him, you know, the idea that I re-
ally had no new factors or anything that bear upon
the sentence that the Court passed. That sentence
was not specifically vacated, but I wanted the Court

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No. 15-2092 7
to be aware, and Mr. Orlando to be aware, that that
was an issue he spoke to me about.
Id. Orlando’s attorney went on to state that if the district
court were to address Orlando’s term of imprisonment, he
would ask the district court to lower his sentence because
Orlando had “been doing well” and the government had
asked for a sentence of 35 years’ imprisonment.
The district court refused and stated that the remand
from the Seventh Circuit was limited to the imposition of
term and conditions of supervised release. There was no di-
rection, according to the district court, “to revisit the time
that I imposed on your sentence.” Id. at 5. Neither the gov-
ernment nor Orlando objected to the district court’s charac-
terization of the remand order.
II. A NALYSIS
On appeal, Orlando advances three arguments: (1) the
district court erred when it failed to conduct a full resentenc-
ing after we remanded in light of Thompson; (2) the district
court committed procedural error when it failed to consider
Orlando’s post-incarceration rehabilitation or the sentencing
factors in imposing its sentence; and (3) the government
breached its plea agreement by not recommending a sen-
tence of 35 years at Orlando’s second resentencing. We ad-
dress each argument in turn.
A. Full Resentencing
The government agrees with Orlando that we should va-
cate his current sentence and order a full resentencing. Of
course, we are not free to remand for resentencing based
solely on the government’s concession that an error occurred
in the district court. Orloff v. Willoughby, 345 U.S. 83, 87

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8 No. 15-2092
(1953) (“This Court, of course, is not bound to accept the
Government’s concession that the courts below erred on a
question of law.”); United States v. Anderson, 547 F.3d 831,
833 (7th Cir. 2008) (“The government has made a limited
confession of error, which of course is not binding on us.”).
We must still determine whether a remand for a full resen-
tencing is warranted.
Our review tells us a full resentencing is appropriate in
this instance. When we first vacated Orlando’s sentence in
March 2015, we remanded to the district court for resentenc-
ing in light of Thompson. In Thompson, we consolidated four
appeals relating to supervised release that were heard on the
same day. 777 F.3d at 372. Finding error with the procedures
used by the district courts in all four cases in imposing con-
ditions and or terms of supervised release, we vacated and
remanded all four cases for a full resentencing. Id. at 382. In
so doing, we stated the following:
Although we find no reversible error in the prison
sentences treated in isolation from the conditions of
supervised release, we vacate the entire sentences be-
cause reconsideration of those conditions may con-
ceivably induce one or more of the judges to alter
the prison sentence that he imposed.
Id. (emphasis added).
When we vacated and remanded in light of Thompson, we
vacated Orlando’s entire sentence, including his term of im-
prisonment, so that the district court would consider Orlan-
do’s supervised release term and conditions along with his

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No. 15-2092 9
term of imprisonment.2 We do the same now. Such recon-
sideration may lead the district court to impose a shorter or
longer term of imprisonment. That is the risk Orlando takes
with this appeal.
B. Consideration of Orlando’s Post-Sentencing Rehabilitation
and Other Sentencing Factors
We need not dwell on Orlando’s second argument con-
cerning the procedural errors committed during his May
2015 resentencing, as we have already determined that Or-
lando is entitled to a full resentencing. The district court mis-
interpreted our remand order. We presume this misinterpre-
tation is why it did not consider the § 3553 factors and why
it may have not discussed the defendant’s post-sentencing
rehabilitation, which the Supreme Court held district courts
may do in Pepper v. United States, 562 U.S. 476, 490 (2011).
We pause here though to make two observations about
the manner in which the term and conditions of supervised
release were addressed during Orlando’s May 2015 resen-
tencing.
First, as we noted at oral argument, the district court did
not impose any term of supervised release, which makes Or-
lando’s sentence defective. 18 U.S.C. § 3583(k) requires that
the district court impose a term of supervised release rang-
ing from 5 years to life on Orlando. Therefore, some term (at
2 It should be noted that neither party directed the district court to this
passage from Thompson during Orlando’s resentencing, after the district
court erred in interpreting our remand order. Had the government and
or Orlando done so, we may not have had to address Orlando’s concerns
here again.

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10 No. 15-2092
least five years) is required. The district court believed it
could delay the imposition of the term until later, but the
statute allowing revision of the conditions of supervised re-
lease does not permit the district court to add a term of su-
pervised release to a sentence entirely lacking it. And, be-
cause Orlando had to receive a term of supervised release,
the district court also needed to, at the very least, impose the
conditions of supervised release required by § 3583(d). That
did not happen at Orlando’s resentencing. We would antici-
pate the government would have called these issues to the
court’s attention at resentencing. It did not. We expect the
result to be different on remand.
Second, during Orlando’s resentencing, the government
and Orlando requested that the district court refrain from
imposing any discretionary conditions of supervised release
until closer to Orlando’s release date. We understand there
are competing views on this wait-and-see approach taken by
district courts within this circuit. This approach has merit,
especially in situations where the defendant faces a long
term of imprisonment. Such an approach may allow a dis-
trict court to impose discretionary conditions that are more
tailored to a defendant’s particular needs should his or her
circumstances change during the term of imprisonment.
And, we have suggested that this approach may be permis-
sible under § 3583(e)(2). See United States v. Neal, 810 F.3d
512, 516–17 (7th Cir. 2016) (recognizing that a district court
may modify or clarify conditions of supervised release long
after imposing supervision)
The approach does, however, present drawbacks. Push-
ing off imposition of discretionary conditions until closer to
a defendant’s release date means that in many circumstanc-

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No. 15-2092 11
es, the district court judge who imposed the original sen-
tence will no longer be on the bench. The new district court
judge then will be deprived of observing and interacting
with the defendant throughout the defendant’s admission of
guilt or the defendant’s trial, as well as the defendant’s ini-
tial sentencing phase. And, even if the same district court
judge is there to consider the imposition of discretionary
conditions at the later date, memories fade, and the court
may lose the benefit of being fully immersed in the case.
Adopting this approach also most likely means the pros-
ecutor and defense attorney who handled the defendant’s
case and initial sentencing will not be around when the dis-
trict court imposes the discretionary conditions of super-
vised release. The defendant’s new attorney may have lim-
ited familiarity with the case and defendant’s situation prior
to the district court imposing a critical piece of the defend-
ant’s sentence.
Finally, it could create a possible scenario where the de-
fendant would not be able to get before the district court
prior to his or her release for the imposition of the discre-
tionary conditions. If this situation were to occur, then sev-
eral of the discretionary conditions—referred to earlier as
“standard”—that allow for an effective system of supervi-
sion would not be in place when the defendant leaves custo-
dy. This approach then breeds inherent inefficiencies, oppor-
tunities for systemic failure, and may even prejudice the de-
fendant. That outcome is not ideal.
Rather than allow for this outcome, the more prudent
path would be to consider and impose mandatory and dis-
cretionary conditions at the defendant’s original sentencing.
Then, as we said in United States v. Siegel, the defendant

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12 No. 15-2092
should on the eve of his or her release from prison “attend a
brief hearing before the sentencing judge (or his successor)
in order to be reminded of the conditions of supervised re-
lease. That would also be a proper occasion for the judge to
consider whether to modify one or more of the conditions in
light of any changed circumstances brought about by the de-
fendant’s experiences in prison.” 753 F.3d 705, 717 (7th Cir.
2014). As discussed earlier, the district court has the power
to modify those conditions under § 3583(e)(2).
C. Plea Agreement
Orlando’s final argument is that the government
breached the plea agreement by failing to recommend a 35
year term of imprisonment. As a consequence of this pur-
ported breach, Orlando seeks a full resentencing hearing be-
fore a different judge. See Santobello v. New York, 404 U.S. 257,
263 (1971) (discussing the remedies for breach of a plea
agreement, which include specific performance and resen-
tencing by a different judge); United States v. Diaz-Jimenez,
622 F.3d 692, 696–97 (7th Cir. 2010).3 Finding no breach here
though, we decline to order that Orlando’s resentencing
hearing be handled by a different judge.
3 Relying on Diaz-Jimenez, Orlando also seeks an order from us requiring
the U.S. Attorney’s Office to assign a different prosecutor for Orlando’s
resentencing. Orlando misreads Diaz-Jimenez. We did not “order” the
U.S. Attorney’s office involved in that case to change the prosecutor who
handled the sentencing. Instead, we stated: “[w]e expect that a different
prosecutor from the U.S. Attorney's office will appear before that judge,
apologize for the clumsy mistake of the previous prosecutor, and rec-
ommend an 18-month sentence without any ifs, ands, or buts.” 622 F.3d
at 697 (emphasis added). That statement does not amount to an order.

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No. 15-2092 13
When a party objects to the breach of a plea agreement at
sentencing and no factual disputes exist, we review whether
the government breached the agreement de novo. United
States v. Malone, 815 F.3d 367, 370 (7th Cir. 2016). We review
for plain error, however, where, as here, the defendant does
not object to the government’s breach of the plea agreement
before the district court. See United States v. Navarro, 817 F.3d
494, 499 (7th Cir. 2016). Under those circumstances, the de-
fendant will only prevail if “there was [an] error; the error
was plain or obvious; the error affected his substantial
rights; and the error seriously affects the fairness, integrity,
or public reputation of judicial proceedings.” United States v.
Artley, 489 F.3d 813, 824 (7th Cir. 2007).
In determining whether there was an error here, we must
analyze whether there was a breach of the plea agreement in
the first instance. To do so, we apply ordinary principles of
contract law in interpreting the agreement, “with an eye to
the special public-interest concerns that arise in this con-
text.” Malone, 815 F.3d at 370 (internal quotation marks omit-
ted). If ambiguities exist in the agreement’s language, we
look to “the parties’ reasonable expectations and construe
ambiguities against the government as the drafter.” Id. But
we will not ignore the plain, unambiguous language of the
agreement and create ambiguities where none exist. Id. To
qualify for a remedy though, the breach must also be materi-
al and not minor. Diaz-Jimenez, 622 F.3d at 694. That is be-
cause a breach that “causes no harm” entitles the non-
breaching party to “nominal damages, which means, as a
practical matter, no relief.” Id.
The clause at issue here states in relevant part that “[t]he
government will recommend a term of imprisonment of thir-

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14 No. 15-2092
ty five years, followed by a term of lifetime supervision.”
(Plea Agreement at ¶22.) This unambiguous term means that
for the government to perform this obligation under the
agreement, it must recommend to the sentencing judge a
term of imprisonment of 35 years for Orlando. It cannot be
stated any plainer. To perform this obligation though, the
government needed the district court sentencing Orlando to
give it the opportunity to do so. No such opportunity was
provided, as the district court refused to entertain any dis-
cussion about Orlando’s term of imprisonment at his resen-
tencing. When the government had an opportunity to rec-
ommend a term of imprisonment at Orlando’s original sen-
tencing, it performed as required by the agreement.
Orlando argues the district court’s error in interpreting
our remand order does not excuse the government’s failure
to recommend a 35-year term of imprisonment. According to
Orlando, the government could not “have misunderstood
the scope of the remand,” as it recognized in the government
and Orlando’s joint motion for resentencing that “Thompson
required a full resentencing.” (Appellant Reply Br. at 3.)
To embrace this line of reasoning would require us to
add a term to the plea agreement, which we refuse to do. No
term in the plea agreement required the government to ar-
gue to the district court that our remand required a full re-
sentencing. Rather, the government was under a contractual
obligation to recommend a 35 year term of imprisonment—if
the district court conducted a full resentencing. The condi-
tion triggering the government’s obligation to perform did
not happen during the May 2015 resentencing.
Further undermining Orlando’s position here is his own
attorney’s belief that our remand order did not allow for the

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No. 15-2092 15
district court to reconsider Orlando’s prison sentence. Or-
lando’s attorney did not object to the district court’s position,
and in fact, suggested that he believed the remand order
“precluded” revisiting his client’s term of imprisonment
during the resentencing.
There is insufficient evidence here to find even a minor
breach of the plea agreement, let alone a material one that
warrants further evaluation under the plain-error standard.
While we did not find breach here, we expect that the prose-
cutor who handles the resentencing hearing on remand will
fulfill the promises made by the government in the plea
agreement, including its promise to recommend 35 years’
imprisonment. See United States v. Cahill, 920 F.2d 421, 425
(7th Cir. 1990) (“[a]ny agreement made by the government
must be scrupulously performed and kept.” (alteration in
original and quotation marks omitted)).
III. CONCLUSION
For the foregoing reasons, Orlando’s sentence is
VACATED, and Orlando’s case is REMANDED for a full re-
sentencing.

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