United States of America v. Valerie Flores

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 18‐3249
U NITED STATES OF A MERICA ,
Plaintiff‐Appellee,
v.
VALERIE FLORES ,
Defendant‐Appellant.
____________________
Appeal from the United States District Court for the
Western District of Wisconsin.
No. 3:18‐cr‐00039‐wmc‐2 — William M. Conley, Judge.
____________________
A RGUED MAY 22, 2019— D ECIDED J ULY 3, 2019
____________________
Before HAMILTON, SCUDDER , and ST . EVE , Circuit Judges.
ST . EVE , Circuit Judge. In this appeal, Valerie Flores chal‐
lenges one condition of her supervised release as unconstitu‐
tionally vague. She admits that she did not raise the chal‐
lenge in the district court, but she asks that we review it for
plain error. The first step in plain‐error review, as the Su‐
preme Court has repeatedly said, is to ask whether the de‐
fendant intentionally relinquished the challenge she now
presents. See Rosales‐Mireles v. United States, 138 S. Ct. 1897,

-- 1 of 14 --

2 No. 18‐3249
1904–05 (2018); Molina‐Martinez v. United States, 136 S. Ct.
1338, 1343 (2016); United States v. Olano, 507 U.S. 725, 733
(1993). This is where Flores’s challenge fails. She had notice
and opportunity to make the challenge in the district court,
she submitted other sentencing challenges, and she affirma‐
tively waived reading of the conditions and their justifica‐
tions at sentencing. Her failure amounts to waiver, preclud‐
ing appellate review.
We recognize, and will address, that in some cases we
have overlooked waiver concerns when reviewing super‐
vised release conditions for plain error. Those cases either
presented compelling reasons for forgiving waiver, which
this case does not present, or simply did not address waiver,
usually because the government did not press it. We empha‐
size, as the Supreme Court has, that waiver is a threshold,
context‐specific inquiry in plain‐error review. Due to Flores’s
waiver, we affirm.
I
In January 2018, Wisconsin law enforcement learned via
confidential informants that Flores and her co‐defendant had
traveled to California to obtain methamphetamine and
transport it back to Wisconsin to sell. Through her cell
phone, the officers tracked Flores and her co‐defendant, who
were driving separate vehicles in tandem. Police conducted
traffic stops after the co‐defendants returned to Wisconsin.
Searches of their vehicles revealed more than 300 pounds of
marijuana with a street value of approximately $1.8 million.
A grand jury returned an indictment charging Flores
with possession with the intent to distribute 100 kilograms
or more of marijuana under 21 U.S.C. § 841(a)(1). Because

-- 2 of 14 --

No. 18‐3249 3
Flores had a prior state court conviction for a felony drug
offense, and was on supervision for that offense at the time
of her arrest, the government filed an information under 21
U.S.C. § 851 for enhanced penalties. Flores faced a mandato‐
ry minimum sentence of ten years and a supervised release
term of eight years. See 21 U.S.C. § 841(b)(1)(B)(vii).
In July 2018, Flores pleaded guilty. Using the 2016 United
States Sentencing Guidelines Manual, the United States Pro‐
bation Office prepared Flores’s Presentence Investigation
Report, Revised Presentence Investigation Report, and ad‐
dendum to the report (collectively “PSR”).
Attached to the PSR was the supervision plan listing the
standard and special conditions of supervised release. At is‐
sue on appeal is standard condition #3 (employment condi‐
tion), which stated: “Defendant shall maintain lawful em‐
ployment, seek lawful employment, or enroll and participate
in a course of study or vocational training that will equip de‐
fendant for suitable employment, unless excused by the pro‐
bation officer or the Court.” In Flores’s supervision plan, the
probation office noted that “defendant’s employment has
been sporadic and inconsistent,” and also “[s]he has out‐
standing financial obligations.” The probation office’s justifi‐
cation for the employment condition stated, in part,
“[e]vidence based practice research indicates that lawful,
stable employment and education are pro‐social activities
that reinforce the rehabilitation of defendant.”
Flores had the opportunity to object to the PSR and dis‐
cuss sentencing issues in writing before sentencing. In Sep‐
tember 2018, she filed objections, corrections, and clarifica‐
tions to the PSR. She did not, however, object to any of the
proposed conditions of supervised release. A couple weeks

-- 3 of 14 --

4 No. 18‐3249
later, she filed a sentencing memorandum seeking the man‐
datory minimum sentence to run concurrently with her state
sentence. Again, Flores did not object to any of the proposed
conditions of supervised release.
The district court conducted Flores’s sentencing hearing
in October 2018. At the beginning of the hearing, the court
asked Flores if she had the opportunity to read and discuss
her original PSR, the revised PSR, and the addendum to the
report with her attorney. Flores responded yes. Next, the
sentencing court noted that the government had no objec‐
tions to the PSR, but that Flores objected to the two‐level in‐
crease under U.S.S.G. § 2D1.1(b)(1) based on maintaining a
premise for manufacturing or distributing a controlled sub‐
stance. The court also discussed Flores’s objection to relevant
conduct explaining that the amounts were not included in
the drug quantity analysis, and therefore, had no impact un‐
der the sentencing guidelines.
Before imposing her sentence, the district judge asked
Flores if there was anything she would like to add. Flores
had prepared a written allocution, which she read into the
record. She emphasized:
I want to use this time serving my sentence for
some major self‐improvement and to acquire skills
and a college degree that will serve me well when I
get home. Whatever the outcome of today ends up
being, I will take every advantage and opportunity
possible to help with my sobriety and restart my
life with a positive perception on how things
should be done rightfully.
After her allocution, the district court sentenced Flores to the
mandatory minimum of 120 months in prison. The court

-- 4 of 14 --

No. 18‐3249 5
recommended mental health treatment, drug abuse pro‐
grams, and, consistent with Flores’s allocution, educational
and vocational training. Also, the court directed that Flores’s
120 month federal sentence run concurrently with the bal‐
ance of her state revocation sentence.
The district court further sentenced Flores to the manda‐
tory eight years of supervised release adopting certain con‐
ditions set forth in the supervision plan, including the em‐
ployment condition. The court first noted that neither the
government nor Flores had objected to these conditions. The
court then stated:
[T]he primary goals of supervised release are to
assist the defendant’s transition back into the
community after a term of imprisonment and to
provide rehabilitation. That will be crucial to this
defendant. Supervision in this case will provide the
typical needed programming, including rehabilita‐
tive programs, assist with community reintegra‐
tion, and afford supervision necessary to deter and
protect against further criminal acts perpetrated by
the defendant.
…
I’m confident that along with her sporadic em‐
ployment and outstanding financial obligations
that I have more than amply justified the conditions
that are being imposed. But as counsel is aware,
there’s some question as to whether I should put
each on the record verbatim and justify them indi‐
vidually. And I’m happy to do that unless the de‐
fense wishes to waive my doing so.
Defense counsel responded: “We do waive, Your Honor.
Thank you.”

-- 5 of 14 --

6 No. 18‐3249
The court continued “when the defendant is released
from confinement, understanding that will be ten years from
now or thereabouts, [if] either the defendant or the supervis‐
ing probation officer should believe that any of the condi‐
tions imposed today are no longer appropriate, they should
petition the Court for review.”
The district court entered judgment on October 9, 2018,
and Flores filed a timely notice of appeal.
II
On appeal, Flores argues that the supervised release con‐
dition requiring her to “maintain lawful employment, seek
lawful employment, or enroll and participate in a course of
study or vocational training that will equip defendant for
suitable employment” is unconstitutionally vague. Flores
specifically takes issue with the word “suitable.”
A
We begin with the difference between forfeiture and
waiver. Waiver occurs when a party intentionally relinquish‐
es a known right and forfeiture arises when a party inad‐
vertently fails to raise an argument in the district court.
Olano, 507 U.S. at 733; United States v. Waldrip, 859 F.3d 446,
450 (7th Cir. 2017). We review forfeited arguments for plain
error, whereas waiver extinguishes error and precludes ap‐
pellate review. Olano, 507 U.S. at 733. Waiver and forfeiture
are related, but distinct, concepts, although at times we have
confused the terms. Waldrip, 859 F.3d at 450; United States v.
Richardson, 238 F.3d 837, 841 (7th Cir. 2001).
Because Flores did not object to the challenged super‐
vised release condition in the district court, the parties assert
that we should review her argument for plain error. We dis‐

-- 6 of 14 --

No. 18‐3249 7
agree. For plain‐error review to apply, “there must be an er‐
ror that has not been intentionally relinquished or aban‐
doned.” Molina‐Martinez, 136 S. Ct. at 1343 (citing Olano, 507
U.S. at 732‐33); see also Rosales‐Mireles, 138 S. Ct. at 1904‐05;
United States v. Young, 908 F.3d 241, 246 (7th Cir. 2018). Ap‐
plying well‐known principles, the record makes clear that
Flores waived her appellate challenge to the employment
condition.
In general, criminal defendants must make informed and
intentional decisions when waiving their rights. New York v.
Hill, 528 U.S. 110, 114 (2000); Olano, 507 U.S. at 733. Even
“[t]he most basic rights of criminal defendants are … subject
to waiver[,]” Peretz v. United States, 501 U.S. 923, 936 (1991),
but “[w]hat suffices for waiver depends on the nature of the
right at issue.” Hill, 528 U.S. at 114. “For certain fundamental
rights, the defendant must personally make an informed
waiver,” but for other rights, “waiver may be affected by ac‐
tion of counsel.” Id.; see also United States v. Babul, 476 F.3d
498, 500 (7th Cir. 2007). Our waiver inquiry, therefore, varies
depending on the right at issue and the circumstances of the
case.
In the context of a guilty plea, for example, because the
defendant is waiving several fundamental rights, her waiver
must clear a high bar. United States v. Brady, 397 U.S. 742, 748
(1970). When accepting a guilty plea, the district judge must
“conduct a long, searching colloquy” to ensure that the de‐
fendant properly waived her constitutional rights. United
States v. Harden, 758 F.3d 886, 888 (7th Cir. 2014); see also Fed.
R. Crim. P. 11(b). Similarly, a defendant’s waiver of her Sixth
Amendment right to assistance of counsel must not only be
knowing and intelligent, but also unequivocal. Iowa v. Tovar,

-- 7 of 14 --

8 No. 18‐3249
541 U.S. 77, 88 (2004); Faretta v. California, 422 U.S. 806, 835
(1975). There, too, the district court must directly engage
with the defendant to confirm that her waiver was knowing
and intelligent.
Not every waiver must meet such stringent criteria. A de‐
fendant waives her right to challenge jury instructions if she
approved of the instructions at the district court. United
States v. Caguana, 884 F.3d 681, 689 (7th Cir. 2018); United
States v. Griffin, 84 F.3d 912, 924 (7th Cir. 1996). “We do not
require the defendant personally to waive objection, nor is
the district court required to address the waiver question di‐
rectly to the defendant.” Griffin, 84 F.3d at 924.
Waiver of most sentencing issues is similar. See United
States v. St. Clair, ‐‐‐ F.3d ‐‐‐‐, 2019 WL 2399597, at *2 (7th Cir.
June 7, 2019). We have observed that there is no rigid rule for
finding waiver in this context. United States v. Butler, 777 F.3d
382, 387 (7th Cir. 2015). Instead, we address each omission in
light of the surrounding circumstances to determine whether
the defendant’s decision not to object was knowing and in‐
tentional. Id.; United States v. Garcia, 580 F.3d 528, 542 (7th
Cir. 2009).
We often find such intent where the defendant chose—as
a matter of strategy—not to present a conditions‐related ar‐
gument to the district court. See, e.g., United States v. Bloch,
825 F.3d 862, 873 (7th Cir. 2016). A strategic decision is, of
course, an intentional one, and we recognize that defendants
often waive sentencing arguments in bargaining with the
prosecution or in focusing the district court on other, more
pressing sentencing issues. We have thus inferred that a de‐
fendant’s choice to raise certain objections at sentencing, but
not others, was strategic and intentional. United States v.

-- 8 of 14 --

No. 18‐3249 9
Tjader, ‐‐‐ F.3d ‐‐‐‐, 2019 WL 2441073, at *2 (7th Cir. June 12,
2019); United States v. Gumila, 879 F.3d 831, 838 (7th Cir.
2018). Indeed, a defendant’s “decision to single out and ob‐
ject to only one condition is the very ‘[t]ouchstone of waiver,’
as it indicates ‘a knowing and intentional decision.’” Bloch,
825 F.3d at 873 (citation omitted). We have also found waiver
when the defendant had a targeted sentencing strategy that
led him to waive certain other sentencing arguments. See
United States v. Barnes, 883 F.3d 955, 957–58 (7th Cir. 2018);
United States v. Walton, 255 F.3d 437, 442 (7th Cir. 2001). All
this stands for a straightforward proposition: In the context
of supervised release conditions, evidence of a strategic rea‐
son not to object in the district court is a sufficient, but not a
necessary, ground on which to find waiver, because it re‐
flects an intentional decision on the defendant’s part.
Moreover, in the specific context of supervised release
conditions, we have provided guidance to ensure defendants
make intentional and informed decisions—decisions that
could eliminate appellate review based on waiver. See United
States v. Lewis, 823 F.3d 1075, 1081–82 (7th Cir. 2016). As we
explained in Lewis, “[t]he foundation for these limits on ap‐
pellate review is that a district judge needs to ensure that
parties have a fair and genuine opportunity to raise objec‐
tions in the district court.” Id. at 1081.
An important factor in giving a defendant the opportuni‐
ty to make an informed and intentional decision about su‐
pervised release conditions is advance notice of the condi‐
tions. United States v. Gabriel, 831 F.3d 811, 814 (7th Cir.
2016); United States v. Kappes, 782 F.3d 828, 842–43 (7th Cir.
2015). “The goal of providing the parties with advance no‐
tice of the conditions at issue is to allow the parties to pre‐

-- 9 of 14 --

10 No. 18‐3249
sent an informed response.” Kappes, 782 F.3d at 843. We re‐
cently clarified why advance notice is necessary in making
an informed decision:
A defendant who receives advance notice of
proposed conditions of supervised release has both
the benefit of advice of counsel and a full oppor‐
tunity to raise objections about arguably vague or
unjustified conditions of supervised release. Sen‐
tencing in the district court is the time to raise such
issues, not on appeal, for the first time.
St. Clair, 2019 WL 2399597, at *2.
Last, and most obvious, we have concluded that a de‐
fendant intentionally waived an appellate challenge to his
supervised release condition when he “affirmatively told the
district court that he had no objection” to the challenged
condition. United States v. Smith, 906 F.3d 645, 650 (7th Cir.
2018); see also United States v. Schrode, 839 F.3d 545, 555 (7th
Cir. 2016) (affirmative withdrawal of objections to chal‐
lenged conditions constitutes waiver). In Smith, when dis‐
cussing defendant’s intentional relinquishment, we reasoned
that the “district court expressly invited objections to the
proposed visitation condition, and Smith’s attorney, with the
benefit of having seen the condition in advance, responded
that the condition was ‘reasonable.’” Id. at 650. We further
articulated that “Smith has not argued that either he or his
attorney was confused or that the response did not indicate
approval.” Id.
Applying these principles to the circumstances of our
case, the record is clear that Flores made a deliberate and in‐
formed decision when she did not challenge the employ‐
ment supervised release condition. She had the opportunity

-- 10 of 14 --

No. 18‐3249 11
to review the probation office’s recommendations with her
attorney in advance of sentencing, and at her sentencing
hearing, the district judge ensured that Flores had reviewed
these conditions with counsel. See St. Clair, 2019 WL 2399597,
at *2; Gabriel, 831 F.3d 814. Counsel also filed written objec‐
tions to the PSR prior to sentencing, objecting to the relevant
conduct calculation and a guideline enhancement, but not
the employment condition. We can reasonably infer from
Flores’s choice to raise certain sentencing objections, but not
others, that her decision was strategic and intentional. See
Gumila, 879 F.3d at 838.
Flores’s decision to waive an explanation and reading of
the supervised release conditions further confirms her in‐
tent. Tjader, 2019 WL 2441073, at *2; Bloch, 825 F.3d at 872–73.
So, too, does the record as a whole. Flores’s allocution re‐
flects her desire to engage in meaningful employment and
educational training to restart her life in a positive manner
once she has served her sentence—another indication that
her decision not to object to the employment condition was
strategic. See Barnes, 883 F.3d at 958.
Due to Flores’s intentional relinquishment of her right to
appeal the claimed error, we are precluded from reviewing
her appellate argument. See Young, 908 F.3d at 246 (“An ap‐
pellate court need not consider a claimed error if the issue
has been waived.”). We affirm on this basis.
B
In so holding, we are aware of the inconsistencies in our
case law and that we have not always applied waiver in this
context. To start, because we liberally construe waiver in fa‐
vor of defendants, see Butler, 777 F.3d at 387, we were willing

-- 11 of 14 --

12 No. 18‐3249
to exercise our discretion and overlook a signed appellate
waiver in the rare and limited instance when a condition
was unconstitutionally vague and overbroad in that it pro‐
hibited activities protected by the First Amendment and “no
reasonable person could know what conduct is permitted
and what is prohibited[,]” in United States v. Adkins, 743 F.3d
176, 193 (7th Cir. 2014). See United States v. Campbell, 813 F.3d
1016, 1018 (7th Cir. 2016). In other cases, we did not address
waiver in light of intervening changes in supervised release
conditions prompted by our decision in United States v.
Thompson, 777 F.3d 368 (7th Cir. 2015). See, e.g., United States
v. Gill, 824 F.3d 653, 661 (7th Cir. 2016); United States v. Pou‐
lin, 809 F.3d 924, 930–31 (7th Cir. 2016). Neither concern is
present here.
In other decisions, we simply did not address waiver
when applying plain‐error review. See, e.g., Kappes, 782 F.3d
at 844; United States v. Ross, 475 F.3d 871, 873 (7th Cir. 2007);
United States v. McKissic, 428 F.3d 719, 721–22 (7th Cir. 2005).
None of these cases, however, held that waiver did not apply
in this context. At most, they assumed that forfeiture gov‐
erned. It is well‐established “that the unexamined assump‐
tions of prior cases do not control the disposition of a con‐
tested issue.” Stanek v. St. Charles Cmty. Unit Sch. Dist. No.
303, 783 F.3d 634, 640 (7th Cir. 2015). And our earlier as‐
sumptions do not withstand scrutiny, as the Supreme Court,
like us, has made clear that waiver is a threshold considera‐
tion when reviewing for plain error. Olano, 507 U.S. at 733;
Young, 908 F.3d at 246.
We make the point again today. When a defendant does
not address supervised release conditions in the district
court, this court will assess whether she waived those chal‐

-- 12 of 14 --

No. 18‐3249 13
lenges. We will find waiver, as we do here, when the de‐
fendant has notice of the proposed conditions, a meaningful
opportunity to object, and she asserts (through counsel or
directly) that she does not object to the proposed conditions,
waives reading of those conditions and their justifications,
challenges certain conditions but not the one(s) challenged
on appeal, or otherwise evidences an intentional or strategic
decision not to object.1
C
On a final note, at oral argument, the government articu‐
lated that it relied on our prior cases when asserting that
plain‐error review applied. See, e.g., Poulin, 809 F.3d at 930–
31. Flores’s appellate counsel countered that the government
waived its waiver defense by agreeing to plain‐error review.
Normally, we would enforce the government’s waiver, but
we are not obligated to do so. See United States v. Combs, 657
F.3d 565, 571 (7th Cir. 2011) (per curiam); United States v.
Schmidt, 47 F.3d 188, 190 (7th Cir. 1995).
Here, we decline to enforce the government’s waiver due
to the inconsistencies in our case law regarding plain‐error
review in the supervised release context, as discussed direct‐
ly above, and our previous confusion over the terms forfei‐
ture and waiver. Further, in the face of the recent influx of
supervised release condition challenges before this court
where such conditions were not challenged before the dis‐
trict court, we are compelled to emphasize that waiver is
part of our plain‐error review.
1 Before issuing this opinion, we circulated it to all judges in active
service under Circuit Rule 40(e). No judge voted to hear this case en banc.

-- 13 of 14 --

14 No. 18‐3249
III
The district court gave Flores every opportunity to make
the challenge she makes now on appeal. Flores expressly de‐
clined. That precludes our appellate review, but it does not
permanently bind Flores. We have long assumed that proba‐
tion officers work with defendants, not against them, to help
defendants transition back into society after prison. They do
not, and must not, nitpick defendants and seek reprimands
or revocations over small, unreasonable concerns. There is
another safety valve as well, even for defendants who waive
conditions challenges on direct appeal. Should certain condi‐
tions prove too onerous or ill‐defined, or should circum‐
stances change during incarceration or after release, 18
U.S.C. § 3583(e)(2) allows defendants like Flores to petition
the court for a modification of their supervised release con‐
ditions, as the district court properly informed Flores here.
For today, however, Flores intentionally waived her right
to challenge the employment condition, and so we affirm.

-- 14 of 14 --