Date: 01-28-2018

Case Style:

Case Number: 17-1628

Judge: Per Curiam

Court: United Stats Court of Appeals for the Seventh Circuit on appeal from the Southern District of Illinois (St. Clair County)

Plaintiff's Attorney: Christopher R. Hoell

Defendant's Attorney: Todd M. Schultz - FPD

Description: The district court sentenced Skylar D. Henshaw,
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.
2 No. 17‐1628
by Henshaw’s counsel. Because we find this departure substantively
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 purchase
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 person.
Agents subsequently entered Henshaw’s residence pursuant
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 dealer,
that Pryor was Henshaw’s recent source for marijuana,
and that Henshaw owed Pryor $30,000 for 30 pounds of marijuana.
But Henshaw represented that he attended the cocaine
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 corroborating
his prior statement to the confidential source regarding
the extent of Henshaw’s involvement in the cocaine
transaction.
At the time of his arrest, Henshaw was subject to a fouryear
felony conditional discharge sentence imposed in Jackson
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.
No. 17‐1628 3
Henshaw pleaded guilty to aiding and abetting Pryor in
attempted possession with intent to distribute cocaine in violation
of 21 U.S.C. §§ 841(a)(1), 841(b)(1)(C), & 846 (Count 1),
and possession with intent to distribute marijuana in violation
of 21 U.S.C. §§ 841(a)(1) & 841(b)(1)(C) (Count 2). Henshaw
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 prior
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. Henshaw’s
sentencing memorandum cited policy disagreements
with the severity of career‐offender enhancements as applied
to offenders with prior drug trafficking (as opposed to violent)
offenses. The memorandum explained that without the
career‐offender designation, Henshaw’s guidelines range
would be 57 to 71 months. The memorandum also represented
that Henshaw had minimal involvement in the underlying
cocaine transaction. Lastly, the memorandum described
Henshaw’s personal history and characteristics, including
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 ar4
No. 17‐1628
rest. Henshaw’s sentencing memorandum requested a sentence
of 57 months. The government did not file a sentencing
memorandum.
At the February 2017 sentencing, the district court adopted
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 guidelines
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 guideline
range of 151 months, three years supervised
release, an appropriate fine to be determined
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
No. 17‐1628 5
low end of the guidelines range that the district court accepted.
The district court described the need for a sentence to reflect
the objectives of just punishment, deterrence, and protecting
the public. The court’s “major concern” with sentencing
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 promote
deterrence as it relates to you.”
The district court nevertheless found a probationary sentence
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 bonehead”
“deci[sion] to help a friend”; (2) the “extremely harsh”
consequences of being a career offender where the “predicate
offenses are drug trafficking offenses” as opposed to violent
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 mistake.”
The government made “a formal objection to the sentence
as being unreasonable” at the end of the hearing.
The government now appeals Henshaw’s sentence.
6 No. 17‐1628
II. ANALYSIS
“In assessing the reasonableness of a sentence,” we first
consider “whether the district court made a procedural mistake
in formulating its sentence,” and then “consider whether
[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 extent
of any variance from the Guidelines range.” Id. at 51. We
do “not apply a presumption of unreasonableness” to a sentence
“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. McIlrath,
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 explain
h[er] conclusion that an unusually lenient or an unusually
harsh sentence is appropriate in a particular case with
sufficient justifications.” Gall, 552 U.S. at 46. “[A] major departure
should be supported by a more significant justification
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
No. 17‐1628 7
reasons for rejecting the thinking of the Sentencing Commission.”).
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 defendant
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 sentenced
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 factors.”
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 offense
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 records
who have been found guilty of similar
conduct.
8 No. 17‐1628
When imposing a sentence of no imprisonment, a district
court must be particularly careful not to “neglect[ ] considerations
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 specific
deterrence. It is difficult to see how a sentence of probation
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 revoked
twice following his earlier misdemeanor assault conviction.
Probation has repeatedly failed to serve as a deterrent
to Henshaw.
The district court recognized the need for specific deterrence.
It expressed “major concern” that Henshaw “had periods
in the past where [he] ha[d] been on probation or supervision
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 appropriately
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 deterring
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
No. 17‐1628 9
United States v. Statham, 581 F.3d 548, 556 (7th Cir. 2009) (vacating
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 imposed”).
The discrepancy in this case between the district
court’s recognition of the failure of probation to deter Henshaw
and the probationary sentence imposed helps illustrate
the sentence’s unreasonableness.
Nor is the sentencing objective of just punishment reflected
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 marijuana
and cash found in Henshaw’s home and the fact that
he admittedly owed Pryor $30,000 for 30 pounds of marijuana
confirm the scale of Henshaw’s marijuana dealing. Henshaw’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, explaining
that “[i]t may be the first opportunity that you have
ever had in your life.” In fact, the record shows that Henshaw
had multiple other opportunities to rebound through lenient
sentences, and he continued to commit crimes. To constitute
just punishment, Henshaw’s sentence needed to reflect
the fact that Henshaw remained a drug dealer despite
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 indictment).
Henshaw’s sentence also needed to reflect “general deterrence”
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 increased
criminal activity is not punished through an increased
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 defendants
with similar records.” 18 U.S.C. § 3553(a)(6). The
district court certainly had discretion to express a policy disagreement
with the career‐offender guidelines as applied to
non‐violent offenders1 and to vary its sentence from the recommended
range on that basis. See, e.g., United States v. Corner,
598 F.3d 411, 416 (7th Cir. 2010) (“a judge … may disagree
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 careeroffender‐
qualifying convictions involved drug trafficking. We note,
however, that as set forth in the PSR adopted by the district court, Henshaw’s
criminal record also included his older conviction for misdemeanor
assault.
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 recommendations,
which reflect (among other things) the goal of avoiding
unwarranted disparities in how different judges treat
equivalent offenses and offenders.” Corner, 598 F.3d at 416.
Even disregarding the career‐offender designation, Henshaw’s
guidelines range would have been 57 to 71 months,
and his probationary sentence would represent a serious difference
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 guidelines
range, they are not so extraordinary as to justify the
degree of departure here. 2 That departure resulted in a substantively
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.”
12 No. 17‐1628
points below that it makes now. The Court agrees with Henshaw
that the government’s failure to file a sentencing memorandum
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 government
did request a 151‐month sentence below, and it objected
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] sentence”
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 discretion
to the sentencing judge.” Id. But we do find “that discretion
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.
No. 17‐1628 13
ROVNER, 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 considered
the nature and circumstances of the offense and Henshaw’s
history and characteristics in selecting a sentence of
probation. As the majority notes, however, that careful consideration
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 supported
by a more significant justification than a minor
one.”). I do not read the majority’s opinion as foreclosing entirely
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 understanding,
I join the majority’s opinion.

Outcome: We VACATE Henshaw’s sentence and REMAND for
proceedings consistent with this opinion.

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