United States of America v. Skylar D. Henshaw

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 17‐1628
U NITED STATES OF A MERICA ,
Plaintiff‐Appellant,
v.
SKYLAR D. HENSHAW,
Defendant‐Appellee.
____________________
Appeal from the United States District Court for the
Southern District of Illinois Division.
No.16 CR 30049 — Staci M. Yandle, Judge.
____________________
A RGUED D ECEMBER 8, 2017 — D ECIDED J ANUARY 18, 2018
____________________
Before KANNE and R OVNER , Circuit Judges, and D URKIN ,
District Judge.
P ER C URIAM. The district court sentenced Skylar D. Hen‐
shaw, a career offender, to five years’ probation–a sentence
151 months lower than the bottom end of his guidelines
range and 57 months lower than the sentence recommended
 Of the Northern District of Illinois, sitting by designation.

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2 No. 17‐1628
by Henshaw’s counsel. Because we find this departure sub‐
stantively unreasonable, we vacate Henshaw’s sentence and
remand for resentencing.
I. BACKGROUND
In July 2015, at the direction of the Drug Enforcement
Agency (“DEA”), a confidential source arranged for the pur‐
chase of a kilogram of cocaine by Henshaw and his friend
Corey Pryor. When the DEA arrested Henshaw during the
purchase on July 14, 2015, he had $3,174 in cash on his per‐
son. Agents subsequently entered Henshaw’s residence pur‐
suant to a search warrant and found $55,090 in cash, 750
grams of marijuana, and five ecstasy pills.
In statements at the time of his arrest and the following
day, Henshaw acknowledged that he was a marijuana deal‐
er, that Pryor was Henshaw’s recent source for marijuana,
and that Henshaw owed Pryor $30,000 for 30 pounds of ma‐
rijuana. But Henshaw represented that he attended the co‐
caine purchase merely to test the cocaine for Pryor. Because
Pryor died before the return of Henshaw’s indictment, the
government could not obtain testimony from him corrobo‐
rating his prior statement to the confidential source regard‐
ing the extent of Henshaw’s involvement in the cocaine
transaction.
At the time of his arrest, Henshaw was subject to a four‐
year felony conditional discharge sentence imposed in Jack‐
son County, Illinois in August 2012 for selling two pounds of
marijuana. He also was subject to a second four‐year felony
conditional discharge sentence imposed in Williamson
County, Illinois in August 2012 for possessing with intent to
deliver over 500 grams of marijuana.

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No. 17‐1628 3
Henshaw pleaded guilty to aiding and abetting Pryor in
attempted possession with intent to distribute cocaine in vio‐
lation of 21 U.S.C. §§ 841(a)(1), 841(b)(1)(C), & 846 (Count 1),
and possession with intent to distribute marijuana in viola‐
tion of 21 U.S.C. §§ 841(a)(1) & 841(b)(1)(C) (Count 2). Hen‐
shaw did not contest the determination in the presentence
investigation report (“PSR”) that he qualified as a “career
offender” under U.S.S.G. § 4B1.1 et seq. based on his two pri‐
or felony controlled substance offenses.
Henshaw had other prior convictions as well, including a
2006 felony conviction for possession of cannabis and a 2004
misdemeanor conviction for assault. For the misdemeanor
assault conviction, Henshaw was sentenced to two years’
probation and eight days in jail. His probation was revoked
twice in that case–once in March 2005 for testing positive for
marijuana and cocaine, and once in July 2006 for unlawfully
possessing 231 grams of marijuana.
Based on Henshaw’s criminal history, the PSR calculated
an advisory sentencing range of 151 to 188 months. Hen‐
shaw’s sentencing memorandum cited policy disagreements
with the severity of career‐offender enhancements as applied
to offenders with prior drug trafficking (as opposed to vio‐
lent) offenses. The memorandum explained that without the
career‐offender designation, Henshaw’s guidelines range
would be 57 to 71 months. The memorandum also repre‐
sented that Henshaw had minimal involvement in the un‐
derlying cocaine transaction. Lastly, the memorandum de‐
scribed Henshaw’s personal history and characteristics, in‐
cluding his family history of drug abuse, physical abuse, and
verbal abuse. It stated that Henshaw was a loving father to
three children and had remained substance free since his ar‐

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4 No. 17‐1628
rest. Henshaw’s sentencing memorandum requested a sen‐
tence of 57 months. The government did not file a sentencing
memorandum.
At the February 2017 sentencing, the district court adopt‐
ed a revised version of the PSR without change, including
the PSR’s finding that Henshaw was a career offender with a
guidelines range of 151 to 188 months. The district court
then said it would entertain arguments under 18 U.S.C.
§ 3553(a).
The government recommended a sentence of the low end
of the guidelines range (151 months). The entirety of the
government’s argument in aggravation was as follows:
Your Honor, I have [no] information that
would take [Henshaw] outside of the guide‐
lines according to the 3553(a) factors and,
therefore, I would recommend, because this
defendant has been relatively cooperative and
he’s been released on bond and has been fairly
compliant as far as I know, the Government
would recommend the low end of the guide‐
line range of 151 months, three years super‐
vised release, an appropriate fine to be deter‐
mined by the Court, and the 200‐dollar special
assessment.
Henshaw’s counsel reiterated the arguments made in his
sentencing memorandum and recommended a sentence of
57 months.
After hearing Henshaw’s allocution, the district court
imposed a sentence of five years’ probation with special
conditions. This represented a 151‐month departure from the

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No. 17‐1628 5
low end of the guidelines range that the district court ac‐
cepted.
The district court described the need for a sentence to re‐
flect the objectives of just punishment, deterrence, and pro‐
tecting the public. The court’s “major concern” with sentenc‐
ing Henshaw was that he “had periods in the past where
[he] ha[d] been on probation or supervision and compliance
ha[d] not been [his] strong card.” “[G]iven that, and your
history,” the court explained, “there without question has
been a lack of respect for the law.” The court further stated
that it was “concerned about the need to facilitate or to pro‐
mote deterrence as it relates to you.”
The district court nevertheless found a probationary sen‐
tence appropriate. It cited a number of factors in support,
including: (1) “the nature and circumstances of the offense,”
which the district court described as a “stupid and bone‐
head” “deci[sion] to help a friend”; (2) the “extremely harsh”
consequences of being a career offender where the “predi‐
cate offenses are drug trafficking offenses” as opposed to vi‐
olent offenses; and (3) Henshaw’s personal characteristics
and family history. The court expressed concern that if it
sentenced Henshaw to incarceration, the employment and
family support he had built since his arrest 19 months earlier
may no longer be available to him. It explained that it was
giving Henshaw “an opportunity to rebound from this mis‐
take.” The government made “a formal objection to the sen‐
tence as being unreasonable” at the end of the hearing.
The government now appeals Henshaw’s sentence.

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6 No. 17‐1628
II. ANALYSIS
“In assessing the reasonableness of a sentence,” we first
consider “whether the district court made a procedural mis‐
take in formulating its sentence,” and then “consider wheth‐
er [the sentence] is substantively reasonable.” United States v.
Brown, 610 F.3d 395, 397–98 (7th Cir. 2010). The government
does not argue–and we do not find–that the district court
made a procedural mistake in sentencing Henshaw. Rather,
the government challenges the substantive reasonableness of
the district court’s sentence.
We review the substantive reasonableness of a sentence
for abuse of discretion. Gall v. United States, 552 U.S. 38, 56
(2007). “When conducting this review, [we] will … take into
account the totality of the circumstances, including the ex‐
tent of any variance from the Guidelines range.” Id. at 51. We
do “not apply a presumption of unreasonableness” to a sen‐
tence “outside the Guidelines range,” id., and there is no
“rigid formula for determining whether the justification for
an out‐of‐range sentence is proportional to the extent of the
sentence’s deviation from the range.” United States v. McIl‐
rath, 512 F.3d 421, 426 (7th Cir. 2008). But “[i]t is also clear
that a district judge must give serious consideration to the
extent of any departure from the Guidelines and must ex‐
plain h[er] conclusion that an unusually lenient or an unu‐
sually harsh sentence is appropriate in a particular case with
sufficient justifications.” Gall, 552 U.S. at 46. “[A] major de‐
parture should be supported by a more significant justifica‐
tion than a minor one.” Id. at 50; see also United States v.
Smith, 811 F.3d 907, 910 (7th Cir. 2016) (“[T]he farther down
the judge goes the more important it is that [she] give cogent

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No. 17‐1628 7
reasons for rejecting the thinking of the Sentencing Commis‐
sion.”).
Henshaw’s sentence unquestionably constitutes a major
departure. It represents a 151‐month variance from the low
end of the guidelines range. This departure resulted in an
unusually lenient sentence of no imprisonment for a defend‐
ant whose own counsel recommended a sentence of well
over four years.
As this Court explained in United States v. Goldberg, 491
F.3d 668 (7th Cir. 2007), “[w]hen the guidelines, drafted by a
respected public body with access to the best knowledge and
practices of penology, recommend that a defendant be sen‐
tenced to a number of years in prison, a sentence involving
no (or … nominal) imprisonment can be justified only by a
careful, impartial weighing of the statutory sentencing fac‐
tors.” Id. at 673. The statutory sentencing factors under 18
U.S.C. § 3553(a) include, as relevant here:
(1) the nature and circumstances of the of‐
fense and the history and characteristics of the
defendant;
(2) the need for the sentence imposed—(A)
to reflect the seriousness of the offense, to
promote respect for the law, and to provide
just punishment for the offense; (B) to afford
adequate deterrence to criminal conduct …
[and]
(6) the need to avoid unwarranted sentence
disparities among defendants with similar rec‐
ords who have been found guilty of similar
conduct.

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8 No. 17‐1628
When imposing a sentence of no imprisonment, a district
court must be particularly careful not to “neglect[ ] consider‐
ations of deterrence and desert.” Goldberg, 491 F.3d at 674.
The primary problem with the sentence in this case is
that it fails to adequately account for considerations of spe‐
cific deterrence. It is difficult to see how a sentence of proba‐
tion could be expected to deter a defendant who has not in
the past been deterred by probation. There is no dispute that
at the time Henshaw committed the crimes at issue, he was
already serving two conditional discharge sentences for
drug‐related crimes. Those conditional discharge sentences
did not deter him from committing the crimes in this case.
And there is no dispute that Henshaw’s probation was re‐
voked twice following his earlier misdemeanor assault con‐
viction. Probation has repeatedly failed to serve as a deter‐
rent to Henshaw.
The district court recognized the need for specific deter‐
rence. It expressed “major concern” that Henshaw “had pe‐
riods in the past where [he] ha[d] been on probation or su‐
pervision and compliance ha[d] not been [his] strong card.”
It explained that “given that, and your history, there without
question has been a lack of respect for the law.” It appropri‐
ately noted, “I am concerned about the need to facilitate or
to promote deterrence as it relates to you. In other words, to
deter you from future crimes.” But it then went on to impose
the very type of sentence that has proven ineffective in de‐
terring Henshaw in the past.
This Court has vacated sentences in cases where there is
a significant discrepancy between the judge’s statements and
the sentence imposed. See, e.g., United States v. Omole, 523
F.3d 691, 696–700 (7th Cir. 2008), abrogated on other grounds by

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No. 17‐1628 9
United States v. Statham, 581 F.3d 548, 556 (7th Cir. 2009) (va‐
cating 51‐month below guidelines variance where judge’s
statements and sentence imposed painted “irreconcilable
pictures”); Brown, 610 F.3d at 399 (vacating 142‐month below
guidelines variance and noting “[t]he contrast between the
tone of the court’s words and the ultimate sentence im‐
posed”). The discrepancy in this case between the district
court’s recognition of the failure of probation to deter Hen‐
shaw and the probationary sentence imposed helps illustrate
the sentence’s unreasonableness.
Nor is the sentencing objective of just punishment re‐
flected in Henshaw’s sentence of probation. It is clear from
the record that accompanying Pryor to the drug purchase
was not simply a one‐off, “stupid and bonehead” “deci[sion]
to help a friend” as the district court characterized it. To the
contrary, Henshaw admitted at the time of his arrest to being
an active marijuana dealer. The substantial amounts of mari‐
juana and cash found in Henshaw’s home and the fact that
he admittedly owed Pryor $30,000 for 30 pounds of marijua‐
na confirm the scale of Henshaw’s marijuana dealing. Hen‐
shaw’s conduct to which he pleaded guilty was part of a
larger, ongoing pattern of drug dealing. But that pattern was
simply not addressed at sentencing.
The district court expressed desire to give Henshaw the
“opportunity to rebound” through a lenient sentence, ex‐
plaining that “[i]t may be the first opportunity that you have
ever had in your life.” In fact, the record shows that Hensh‐
aw had multiple other opportunities to rebound through le‐
nient sentences, and he continued to commit crimes. To con‐
stitute just punishment, Henshaw’s sentence needed to re‐
flect the fact that Henshaw remained a drug dealer despite

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10 No. 17‐1628
the generous opportunities he had been given. Compare Gall,
552 U.S. at 41–60 (finding 30‐month downward variance of
probation substantively reasonable for defendant with “no
significant criminal history” who “self‐rehabilitated” and
had not sold drugs for years prior to the return of the in‐
dictment).
Henshaw’s sentence also needed to reflect “general de‐
terrence” objectives “of preventing like or related crimes.”
United States v. Molton, 743 F.3d 479, 486 (7th Cir. 2014). A
sentence of probation after multiple prior, serious offenses
does not serve the purpose of general deterrence. If in‐
creased criminal activity is not punished through an in‐
creased sentence, without at least some compelling reason
for not doing so, then others will not be sufficiently deterred
from repeated criminal activity.
Finally, Henshaw’s sentence needed to account for “the
need to avoid unwarranted sentence disparities among de‐
fendants with similar records.” 18 U.S.C. § 3553(a)(6). The
district court certainly had discretion to express a policy dis‐
agreement with the career‐offender guidelines as applied to
non‐violent offenders 1 and to vary its sentence from the rec‐
ommended range on that basis. See, e.g., United States v. Cor‐
ner, 598 F.3d 411, 416 (7th Cir. 2010) (“a judge … may disa‐
gree with the Commission’s recommendation categorically,
as well as in a particular case,” and may sentence a career
offender below the guidelines range on that basis); United
1 The district court correctly explained that Henshaw’s career‐
offender‐qualifying convictions involved drug trafficking. We note,
however, that as set forth in the PSR adopted by the district court, Hen‐
shaw’s criminal record also included his older conviction for misde‐
meanor assault.

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No. 17‐1628 11
States v. Price, 775 F.3d 828, 840 (7th Cir. 2014) (“the district
court’s sentencing discretion includes the option to vary
from the guidelines ‘based on a policy disagreement with
them’”) (quoting Spears v. United States, 555 U.S. 261, 264
(2009)) (emphasis in original). But the district court also
“need[ed] to understand the Commission’s recommenda‐
tions, which reflect (among other things) the goal of avoid‐
ing unwarranted disparities in how different judges treat
equivalent offenses and offenders.” Corner, 598 F.3d at 416.
Even disregarding the career‐offender designation, Hen‐
shaw’s guidelines range would have been 57 to 71 months,
and his probationary sentence would represent a serious dif‐
ference in treatment compared to defendants with similar
records. For that reason, Henshaw’s probationary sentence
failed to “avoid unwarranted sentence disparities.” 18 U.S.C.
§ 3553(a)(6).
Although other considerations cited by the district court,
including Henshaw’s troubled family history and concerns
that a criminal sentence would impact his employment and
family support, may warrant a departure from the guide‐
lines range, they are not so extraordinary as to justify the
degree of departure here. 2 That departure resulted in a sub‐
stantively unreasonable sentence.
In his brief and at oral argument, Henshaw emphasized
that the government failed to file a sentencing memorandum
and thus squandered an opportunity to make many of the
2 Henshaw’s counsel acknowledged at sentencing that the 57‐month
sentence he recommended would not have the same devastating impact
on Henshaw’s family members that “a sentence of something like 151
months would.”

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12 No. 17‐1628
points below that it makes now. The Court agrees with Hen‐
shaw that the government’s failure to file a sentencing mem‐
orandum and its very brief argument at sentencing poorly
served the district court. The government made its best (and
its only substantive) arguments on appeal. But the govern‐
ment did request a 151‐month sentence below, and it object‐
ed to the reasonableness of Henshaw’s sentence after it was
imposed.
In any event, the government’s approach does not
change the district court’s obligations. The district court had
an obligation to apply § 3553(a), and the question before this
Court is whether the district court “abused [its] discretion in
determining that the § 3553(a) factors supported [the] sen‐
tence” in question. Gall, 554 U.S. at 56. We conclude that an
abuse of discretion occurred.
Like the sentence of one day of imprisonment in Goldberg,
Henshaw’s sentence “neglected considerations of deterrence
and desert.” 491 F.3d at 674. As in Goldberg, “[w]e do not
rule that a sentence below … [the] guidelines range would
have been improper in this case.” Id. And we reiterate that
“the statutory sentencing factors … leave plenty of discre‐
tion to the sentencing judge.” Id. But we do find “that discre‐
tion was abused in this case.” Id. The case therefore must be
remanded for resentencing.
III. CONCLUSION
We VACATE Henshaw’s sentence and REMAND for
proceedings consistent with this opinion.

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No. 17‐1628 13
R OVNER , Circuit Judge, concurring. I join the majority’s
opinion vacating and remanding Skylar Henshaw’s sentence
for resentencing. I write separately simply to reiterate that
the district court here very carefully and thoroughly consid‐
ered the nature and circumstances of the offense and Hen‐
shaw’s history and characteristics in selecting a sentence of
probation. As the majority notes, however, that careful con‐
sideration was not offset by a thorough enough explanation
as to why the sentence of probation adequately reflects the
seriousness of the offense, provides just punishment, and
affords adequate deterrence. See, e.g., Gall v. United States,
552 U.S. 38, 50 (2007) (“[A] major departure should be sup‐
ported by a more significant justification than a minor
one.”). I do not read the majority’s opinion as foreclosing en‐
tirely the possibility that a sentence of probation could be
reasonable if the court more thoroughly explained how such
a sentence might still specifically deter Henshaw from future
crime in light of the specifics of this offense. With that un‐
derstanding, I join the majority’s opinion.

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