United States of America v. Gregory A. Glosser

In the
United States Court of Appeals
For the Seventh Circuit
No. 08-4015
UNITED STATES OF AMERICA,
Plaintiff-Appellant,
v.
GREGORY A. GLOSSER,
Defendant-Appellee.
Appeal from the United States District Court
for the Central District of Illinois.
No. 07 CR 20042—Michael P. McCuskey, Chief Judge.
ARGUED NOVEMBER 5, 2009—DECIDED SEPTEMBER 29, 2010
Before BAUER, MANION, and WILLIAMS, Circuit Judges.
WILLIAMS, Circuit Judge. The government appeals
from a 121-month sentence a defendant received for
attempting to possess more than 500 grams of metham-
phetamine, arguing that the district court committed
procedural error by announcing and promising that it
would impose the mandatory minimum sentence during
the change of plea hearing, before it knew the advisory
guidelines range or had heard either party’s argument

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2 No. 08-4015
regarding the sentence. Although we recognize that the
court’s references to the ten-year mandatory minimum
stemmed from a desire to ensure the defendant under-
stood the minimum time he faced (he had previously
been incorrectly informed that he faced a statutory mini-
mum of five years), we agree with the government that
the premature announcement of sentence constitutes
procedural error that requires we vacate the sentence
and remand for further proceedings.
I. BACKGROUND
After being arrested while possessing methamphet-
amine, John Sims agreed to cooperate with law enforce-
ment authorities and identified Gregory Glosser as a
person selling methamphetamine in the Charleston,
Illinois area. Sims wore a wire during a meeting with
Glosser, and Glosser expressed his desire for metham-
phetamine to resell. Glosser also said that if Sims could
not obtain the drugs, Glosser would go to Oklahoma
to get the methamphetamine on his own. About a
week later, law enforcement agents arranged for Sims to
meet with Glosser. Sims told Glosser he had a pound-and-
a-half of methamphetamine in the packages he had with
him, and Glosser responded that they would make
about $57,000 when they resold it. After Sims gave the
packages to Glosser, law enforcement agents placed
Glosser under arrest. He was read his Miranda warnings
and admitted that he intended to resell the methamphet-
amine in gram quantities.
Glosser was charged with a single count of attempting
to possess 500 or more grams of a substance con-

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No. 08-4015 3
taining methamphetamine, in violation of 21 U.S.C.
§ 841(a)(1) and (b)(1)(B)(viii). He entered a plea of not
guilty. The morning that trial was to begin, however,
Glosser’s attorney told the court that he had decided to
plead guilty. The court then engaged in a lengthy dis-
cussion with Glosser to ensure he was pleading guilty
knowingly and voluntarily. At one point, the court
asked the prosecutor whether Glosser had any felony
convictions, and the prosecutor responded that he was
not aware of any. Defense counsel also agreed, but when
the court asked Glosser, Glosser volunteered that he pled
guilty to a felony count of obstruction of justice in 1987.
When the court asked whether that meant he had a
state court felony for which he had received probation,
Glosser answered that was not correct and said his sen-
tence had been sixty days in jail.
Reading from the government’s original filing with the
court, the judge told Glosser that by pleading guilty, he
would receive a mandatory minimum sentence of five
years in prison with a maximum term of forty years.
The prosecutor interjected and stated that he had ex-
plained to defense counsel that morning that under
the applicable statute, the mandatory minimum was
actually ten years’ imprisonment, with a maximum of
life imprisonment. Glosser responded that he was not
aware of the ten-year mandatory minimum and stated
he had been told when he was arraigned before a dif-
ferent judge that he faced five to forty years’ imprison-
ment. The prosecutor stated that Glosser would not
receive a forty-year sentence, and the court clarified
that the mandatory minimum sentence was ten years.

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4 No. 08-4015
Glosser responded that he understood, but then said
that he had been under the impression during the ten
months since his arraignment that he faced five to forty
years in custody. The court explained that the ap-
plicable minimum sentence was ten years unless he
cooperated and the government made a motion for a
downward departure, and the court also made clear
that the government had not promised to make such a
motion. The court further stated, “The only promise or
prediction that I can make to you at this moment is there
is nothing that would cause me, from what I’ve seen in
this case and have heard of your background, nothing
that would cause me to sentence you any more than
what Congress mandates I must do, a minimum of ten.”
After again clarifying that the government had made
no promise that it would move for a downward depar-
ture, the court stated, “Well, I’ve given you the biggest
promise I can give you. It’s not a life case. It’s not a 40-
year case. It’s a 10-year case. So that’s as good as I can
give you, but I can’t give you one day less than ten
years.” Glosser reiterated his position that the way the
indictment was written was contradictory to what he
was being told, and the court again explained that the
charge carried a ten-year mandatory minimum. As the
court went through the elements of the charge and asked
Glosser if he had any questions, Glosser responded that
he did have a question—the way he read the statute, he
said, possessing 100 to 999 grams of a mixture con-
taining methamphetamine for a person with no prior drug
convictions carried a five to forty-year sentence. The
court once again explained that the charge against Glosser

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No. 08-4015 5
carried a ten-year minimum. Glosser replied that he
understood and stated that he still wished to plead guilty.
The court then discussed the consequences of giving
up the right to a jury trial, and the government estab-
lished a factual basis for the plea. The following exchange
then occurred:
Court: With no force, threats, or promises other
than the Court saying to you that if you
plead guilty and I accept it, the mini-
mum sentence would be ten years, and
that would be the sentence that I would
impose, are you pleading guilty under
all of those factors because you did, in
fact, do what the government’s charged
you with, and you are guilty of the mat-
ter in the indictment?
Glosser: Yes, your Honor.
AUSA: Your Honor, if I may, I just want to be
clear because I had heard you when you
stated initially that your best guess
would be that you would impose that
minimum sentence based on the facts
you have before you now.
I just want to make it clear we haven’t
taken a position as to what sentence—
Court: I fully intend that the government will
stand up here and ask for more than ten
years, but I haven’t heard anything in
this case—and I’ve heard more about

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6 No. 08-4015
this case probably than any case I’ve
ever had with all of the hours we spent
in court, all of the facts presented, all of
the filings. So I can’t imagine that there’s
anything in this case that would sur-
prise me, and that he even admitted a
felony . . . that you didn’t tell me about.
This is a case, as far as I’m concerned
from what I’ve seen, that Congress has
got it at the maximum—at ten years to
me is a stiff sentence, and the mandatory
minimum ten years—I can’t imagine
that I’ve promised him anything that
I wouldn’t do. I fully expect you’ll ask
for more, and I fully expect that I’ll find
a reason not to give it to you.
AUSA: Okay. I just want to make it clear that
the Court isn’t foreclosing the govern-
ment from presenting any evidence as
we go forward to sentencing.
Court: Oh, no.
AUSA: Thank you.
Court: But, I mean, I haven’t seen a prior rec-
ord that would justify more than ten. I
haven’t seen anything about this that
would require more than ten. And so
I’m making that promise to [defense
counsel] and Mr. Glosser because I in-
tend to carry it out and articulate many

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No. 08-4015 7
reasons why ten is, if anything, more
than sufficient, more than reasonable,
maybe even excessive; but that’s what
Congress says. Ten is it, and that is my
promise.
But you can present and make your
record . . . . You will have that ample
opportunity to present all of those
facts to this Court so that if Mr. Glosser
ultimately appeals his sentence, the
Seventh Circuit Court of Appeals can
say, “You’re right. Judge McCuskey
made a mistake. Mr. Glosser’s wrong.
The government’s right. He gets a
greater sentence than ten years.” That
opportunity will be made. You’ll have
a chance to make your record, and
Mr. Glosser will have an opportunity
to throw open the door to that cross-
appeal on whatever record you make
at sentencing. But I’ve made it clear
where I’m at. Mr. Glosser, do you have
any questions where I’m at?
Glosser: No, your Honor. You’ve made it very
clear.
Court: Are you asking me to accept this plea, to
enter a judgment of conviction on the
matter contained in the indictment
with the only promise made that if
I accept it I’ll sentence you to ten years?

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8 No. 08-4015
Glosser: Yes, Your Honor. That’s what I under-
stand.
. . . .
Court: Any hesitation?
Glosser: Ten years is a long time.
Court: Ten years is a long time. That’s what my
promise is. It’s a long time. . . .
The court concluded that Glosser was pleading
guilty because he was, in fact, guilty to the matter
charged in the indictment. The court also determined
that Glosser entered the plea knowingly and stated
Glosser “understands that the Court has promised him
a mandatory sentence of ten years at sentencing” and
that Glosser was pleading guilty under those facts
and circumstances.
The probation office prepared a Presentence Investiga-
tion Report (“PSR”) before the sentencing hearing. It
placed Glosser in criminal history category I, the lowest
category, and it recommended an advisory guidelines
range of 188 to 235 months’ imprisonment. Also prior
to the sentencing hearing, the government filed a
motion asking the court to clarify that Glosser acknowl-
edged that his guilty plea was not induced by any
promise of a specific sentence and understood that
the court could sentence him within the statutory range
of ten years to life in prison.
The court referenced the government’s motion at the
sentencing and reviewed the change of plea hearing in

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No. 08-4015 9
detail. The court stated that the reason it had discussed
the mandatory minimum sentence at the plea hearing
was so that Glosser would not be confused as to the term
that he faced. After hearing the parties’ arguments, over
the government’s objection, and against the PSR’s recom-
mendation, the court gave Glosser a two-level reduction
for acceptance of responsibility. In doing so, it pointed
to Glosser’s plea of guilty, its belief that his acceptance
of responsibility was genuine, and his correction of the
record regarding his prior felony conviction. That reduc-
tion lowered the guidelines range to 151 to 188 months.
Next, the court acknowledged that under U.S.S.G.
§ 5H1.11, military, civic, and employment-related con-
tributions generally were not relevant in determining
whether a departure was warranted. Pointing out that
it did not think it had ever sentenced a defendant in a
drug case with as good a work history as Glosser’s, as
well as Glosser’s four years of active duty service as a
Marine with an honorable discharge and the fact that
two of his ex-wives and a former attorney had writ-
ten letters on his behalf, the court stated it found these
considerations warranted a two-level reduction in this
case. The resulting advisory guidelines range was 121 to
151 months’ imprisonment. The government, on the
other hand, requested a 210-month sentence, a sentence
it argued was appropriate in part because of firearms
found at Glosser’s residence.
The court imposed a sentence of 121 months’ imprison-
ment and ruled that the sentence was sufficient but not
greater than necessary to punish Glosser. It stated that
although it had previously told Glosser the sentence

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10 No. 08-4015
would be for 120 months, it was adding an extra thirty
days’ imprisonment in light of the hassle he had given the
court, which was partly a reference to frivolous filings
Glosser had made. The government appeals from the
sentence Glosser received.
II. ANALYSIS
The government maintains that the district court
erred by announcing that it would sentence Glosser to
the mandatory minimum of ten years in prison before
it knew the advisory sentencing guidelines range or had
heard the parties’ positions regarding Glosser’s sen-
tence. In doing so, the government contends that the
district court committed a procedural error that requires
resentencing. We review the procedures followed by
the district court in sentencing de novo. United States v.
Gibbs, 578 F.3d 694, 695 (7th Cir. 2009).
Even though the United States Sentencing Guide-
lines are advisory, the Supreme Court has said that
“a district court should begin all sentencing proceedings
by correctly calculating the applicable Guidelines range.
As a matter of administration and to ensure nationwide
consistency, the Guidelines should be the starting point
and the initial benchmark,” and the court is to “remain
cognizant of them throughout the sentencing process.” Gall
v. United States, 552 U.S. 38, 49, 50 n.6 (2007). Consistent
with the Supreme Court’s direction, we have repeatedly
said that in determining a defendant’s sentence, the
procedure a judge is to follow begins with first correctly
calculating the advisory guidelines range. United States

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No. 08-4015 11
v. Omole, 523 F.3d 691, 697 (7th Cir. 2008). Next, after
hearing the parties’ arguments, the judge is to consider
the factors spelled out in 18 U.S.C. § 3553(a) to decide
whether the defendant’s sentence should fall within
that guidelines range or elsewhere. Id. When reviewing
a sentence, the Supreme Court has directed that we
“must first ensure that the district court committed no
significant procedural error.” Gall, 552 U.S. at 51.
The district court’s references to a ten-year mandatory
minimum sentence during the change of plea hearing
were undoubtedly motivated in large part by a desire to
ensure that Glosser understood he was facing more
than the five- to forty-year sentence he initially thought
he faced. It was no doubt frustrating to have a de-
fendant repeatedly raise the incorrect statutory range,
even after it had been clarified numerous times, and the
district court’s desire and efforts to ensure that Glosser
clearly understood the applicable statutory minimum
sentence are commendable. And we commend the court
on the very thorough discussion it had with Glosser to
ensure that he understood the ramifications of a guilty
plea before he entered it. Nonetheless, we agree with
the government that a procedural error took place here.
Cf. United States v. Vrdolyak, 593 F.3d 676, 683-84 (7th
Cir. 2010) (remanding for resentencing where circum-
stances suggested that district court had committed to
a noncustodial sentence for the defendant). When the
district court made its repeated assurances at the change
of plea hearing that it would impose a ten-year sentence,
it did so without knowing the advisory guidelines
range, as evidenced by its explicit statement during

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12 No. 08-4015
the hearing that it did not know the range. The
court also had not yet heard the parties’ positions on
sentencing. Nor had it received the probation office’s
PSR. And it is clear that the court went beyond simply
explaining the consequences of a guilty plea, as it re-
peatedly “promised” Glosser a sentence of ten years.
The next question is whether we must order a new
sentencing hearing in this case in light of the procedural
error. Glosser emphasizes that the government does not
maintain that his sentence is unreasonable. Therefore,
he argues, his sentence should be upheld. It is true that
the guidelines are only advisory, and that the district
court gave a thorough explanation for why it chose
the sentence it did. But even if the sentence were indep-
endently reasonable, an issue on which we take no posi-
tion, we cannot let it stand if the procedural error
was egregious. See United States v. Abbas, 560 F.3d 660, 667
(7th Cir. 2009) (“It is important to emphasize that . . . our
harmless error determination and review of the sen-
tence’s reasonableness are separate steps.”).
Indeed, both parties have argued that if there was an
error, harmless error review applies. The Supreme
Court has stated that an error is harmless when the
error “did not affect the district court’s selection of the
sentence imposed.” Williams v. United States, 503 U.S. 193,
203 (1992); Abbas, 560 F.3d at 667. When we are con-
vinced the sentence would have been the same absent
the error, we deem the error harmless. Abbas, 560 F.3d
at 667. We have found some procedural errors in sen-
tencing harmless where the district court made it clear

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No. 08-4015 13
that it would have imposed the same sentence even if the
error had not been made. See id. (finding error in im-
posing U.S.S.G. § 2C1.1 enhancement harmless where
sentencing judge explicitly stated it would have im-
posed same sentence even if § 2C1.1 did not apply);
United States v. Anderson, 517 F.3d 953, 965-66 (7th Cir.
2008) (deeming error in calculating net benefit harmless
where court stated at sentencing it would impose same
sentence even if its benefit calculation was incorrect);
United States v. Jackson, 549 F.3d 1115, 1118 (7th Cir.
2008) (finding error in offense classification harmless
where sentencing judge explained that it would have
imposed the same sentence regardless of whether
offense was a “crime of violence”); United States v.
White, 519 F.3d 342, 349 (7th Cir. 2008) (upholding sen-
tence imposed before Supreme Court clarified that
judges could consider the Guidelines’ crack/powder
cocaine disparity where sentencing judge made clear
it would have imposed the same sentence regardless of
any guidelines). On the other hand, when we are not
certain that the sentencing judge would have imposed
the same sentence had it not committed a procedural
error, we have declined to find the error harmless. See, e.g.,
United States v. Zahursky, 580 F.3d 515, 528 (7th Cir.
2009) (remanding for resentencing where district court’s
statements did “not approach the firm assurances that
we had in the cases where we have found a sentencing
error harmless”); United States v. Edwards, 581 F.3d 604,
613 (7th Cir. 2009) (remanding for a further sentencing
hearing where it was unclear whether a procedural
error had occurred that affected the choice of sentence);

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14 No. 08-4015
see also Gibbs, 578 F.3d at 695-96 (remanding for resen-
tencing where district court committed procedural
error by failing to calculate advisory guideline range
for supervised release term).
Although both parties argue that harmless error
review applies, the harmless error construct does not fit
our case as easily as it did in Abbas, Anderson, and other
cases where the error was in a guidelines calculation.
That is, one might be inclined to say that the district
judge’s actions suggest it would have imposed the
same sentence even if it had not explicitly stated it
would do so at the earlier hearing, and that the error
was therefore harmless and the sentence should stand.
We conclude otherwise. Although the district court gave
several reasons at the sentencing hearing for imposing
a below-guidelines sentence of 121 months, we are not
confident that it would have done so if it had not
decided it would impose the mandatory minimum sen-
tence when Glosser changed his plea to guilty. The court
made repeated statements at the change of plea hearing
that it was promising a mandatory minimum sentence.
It also said then that it expected the government to argue
for a higher sentence, but, notably, that it would find
a reason to impose a sentence of ten years. And at the
sentencing hearing, although it gave independent rea-
sons for imposing the sentence it did, the judge explained
that the sentence of 121 months differed from what it
had decided at the previous hearing only because it
was imposing an additional thirty days for all that
Glosser had put the court through. These comments
do not assure us that the reasons articulated at the sen-

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No. 08-4015 15
tencing hearing were truly independent, and not
motivated by the earlier decision and promise.
Moreover, allowing this sentence to stand as harmless
based on the district court’s comments would lead to
an odd result, as a prematurely determined sentence
should not be insulated from review by a judge’s later
announcement that it would have imposed the same
sentence. So whether viewed under harmless error
review or as a fundamental procedural error, see Puckett
v. United States, 129 S. Ct. 1423, 1432 (2009) (discussing
“structural” errors, including those that “defy analysis
by ‘harmless-error’ standards” by affecting entire
adjudicatory framework); Gibbs, 578 F.3d at 695-96 (re-
manding in light of procedural error at sentencing with-
out resort to harmless error analysis), the result is the
same. While we acknowledge the quandary the district
court faced by Glosser’s repeated expressions that he
wanted to plead guilty yet incorrectly thought the ap-
plicable mandatory minimum was a five-year sentence,
we vacate Glosser’s sentence and remand for a new sen-
tencing hearing.
We also note that although neither party challenges
Glosser’s guilty plea at this juncture, we have some
concerns about its validity. Glosser decided to plead
guilty the morning he was to begin trial and did not
sign a written plea agreement. At the hearing, he ex-
pressed repeated concerns about the sentence and only
pled guilty after being promised he would receive a
sentence of ten years’ imprisonment. To avoid any ques-
tion about the plea’s validity, we suggest that the new

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16 No. 08-4015
district court judge on remand conduct a new plea
hearing to ensure that Glosser knowingly and vol-
untarily desires to plead guilty, with the knowledge that
he will receive a sentence of at least ten years’ impris-
onment and that he could receive as much as life impris-
onment.
III. CONCLUSION
Glosser’s sentence is VACATED, and this case is
REMANDED for further proceedings consistent with
this opinion. Circuit Rule 36 shall apply on remand.
9-29-10

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