Derek Fields v. USA

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 24-2913
D
EREK FIELDS,
Petitioner-Appellant,
v.
U
NITED STATES OF AMERICA,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Northern District of Indiana, South Bend Division.
No. 3:21-cv-466 — Cristal C. Brisco, Judge.
____________________
ARGUED APRIL 16, 2026 — DECIDED AUGUST 17, 2026
____________________
Before HAMILTON, LEE, and TAIBLESON, Circuit Judges.
TAIBLESON, Circuit Judge. After rejecting multiple plea of-
fers, Derek Fields was convicted by a federal jury of crimes
arising from a violent kidnapping. He was ultimately sen-
tenced to 43 years’ imprisonment. Now, Fields has moved for
relief under 28 U.S.C. § 2255, arguing that his counsel was in-
effective for failing to provide enough advice about a plea of-
fer that, he claims, the Government extended to Fields during
jury selection. According to Fields, he rejected that plea offer

2 No. 24-2913
because his trial counsel only informed him that it carried 37
years’ imprisonment, with no other details.
The district court denied Fields’s motion without an evi-
dentiary hearing, and we affirm. Even assuming that the late-
breaking plea offer existed and that Fields’s counsel provided
deficient advice about it, Fields has not shown that he would
have accepted it and received a lower sentence as a result. He
therefore has not demonstrated the requisite prejudice to suc-
ceed on an ineffective-assistance-of-counsel claim. The district
judge thus did not abuse her discretion in denying Fields’s
motion without an evidentiary hearing.
I. Background
A.
In the early hours of September 8, 2015, Fields and his
codefendants kidnapped Adrian Harris, an acquaintance of
Fields’s, at gunpoint. During the kidnapping, one defendant
accidentally shot Harris in the arm. Over the course of about
five hours, Fields and his codefendants restrained, gagged,
and blindfolded Harris—all while beating him and demand-
ing a ransom that was paid by his sister. Fearing that Harris
would die, Fields and his codefendants ultimately dropped a
blindfolded Harris in an alley; he was rescued soon after.
1

The crime was not a whodunnit: Just two days after the
kidnapping, Fields was arrested pursuant to a federal crimi-
nal complaint charging him with kidnapping, making a ran-
som demand, and possessing a firearm as a felon. His two

1
Additional facts underlying Fields’s charges and conviction are de-
tailed in our prior opinion, United States v. Brazier, 933 F.3d 796 (7th Cir.
2019).

No. 24-2913 3
codefendants were arrested around the same time. In October
of 2015, a grand jury indicted Fields and his codefendants on
the three charges in Fields’s criminal complaint, plus a charge
of discharging a firearm during a crime of violence in viola-
tion of 18 U.S.C. § 924(c)(1)(A)(iii).
The Government extended multiple plea offers to Fields,
both before and after his indictment. Those offers each carried
a mandatory minimum term of imprisonment under 18 U.S.C.
§ 924(c)—either a seven-year minimum for brandishing a fire-
arm during a crime of violence, see § 924(c)(1)(A)(ii), or a ten-
year minimum for discharging a firearm during a crime of vi-
olence, see § 924(c)(1)(A)(iii). Each plea offer also contem-
plated a substantial Guidelines imprisonment range.
Fields rejected these offers after consulting with his then-
attorney, Fred Hains. We discuss those consultations in more
detail below. Here, it suffices to note that according to Hains,
Fields was “adamant” about rejecting plea offers that carried
prison time over about 20 years, which Fields viewed as “a
lifetime sentence.” That remained true across multiple meet-
ings with Hains considering multiple plea offers, even though
Fields and Hains also discussed “the fact that [Fields] was ba-
sically screwed” given the evidence against him.
Hains eventually withdrew as Fields’s counsel, and Fields
cycled through new attorneys. He landed on attorney Philip
Skodinski, who (unlike prior counsel) indulged Fields’s re-
quest to file a motion to suppress certain evidence. That mo-
tion was denied, and Fields proceeded to trial. After a three-
day trial in November of 2016, a jury found Fields guilty on
all charges. The district judge sentenced Fields to 636 months’
(53 years’) imprisonment.

4 No. 24-2913
Fields appealed, arguing for the first time that his convic-
tion for discharging a firearm during a crime of violence un-
der 18 U.S.C. § 924(c) was invalid because federal kidnapping
is not a “crime of violence.” A fter oral argument, the Supreme
Court decided United States v. Davis, 588 U.S. 445 (2019),
which resolved the “crime of violence” question in Fields’s fa-
vor. So we vacated his § 924(c) conviction. United States v. Bra-
zier, 933 F.3d 796, 800–02 (7th Cir. 2019). On remand, Fields
was resentenced without the ten-year § 924(c)(1)(A)(iii) man-
datory minimum, to 516 months’ (43 years’) imprisonment.
B.
After his conviction was final, Fields filed a motion under
28 U.S.C. § 2255. Under that provision, a federal prisoner may
move to “vacate, set aside or correct [a] sentence” if it was
“imposed in violation of the Constitution or laws of the
United States.” 28 U.S.C. § 2255(a). Fields argued that his sen-
tence had been tainted by ineffective assistance of counsel in
violation of the Sixth Amendment—specifically, by Skodin-
ski’s inadequate advice in connection with a plea offer.
In a declaration accompanying his § 2255 motion, Fields
alleged that during jury selection, Skodinski had passed him
a plea agreement offered by the Government and instructed
him to “just read it.” According to Fields, when he asked
Skodinski “what it was,” Skodinski “told [him] it was a ‘37-
year plea.’” Skodinski purportedly provided no other advice,
and so Fields rejected the offer. In his § 2255 motion, Fields
argued that “but for” Skodinski’s “deficient advice[,] there is
a reasonable probability [that] Fields would have pleaded
guilty and been sentenced to less jail time.” Fields did not,
however, attach the plea agreement, nor did he describe any
of its terms beyond it being a “37-year plea.”

No. 24-2913 5
In its opposition to Fields’s § 2255 motion, the Govern-
ment recounted the extensive plea negotiations that took
place while Hains represented Fields, relying in part on an af-
fidavit from Hains that described these negotiations from the
defense’s perspective. According to the Government, it did
not extend any “further offers” to Fields’s subsequent coun-
sel, including Skodinski. The Government also submitted an
affidavit from Skodinski, who averred that he did not pass
Fields a plea agreement during jury selection because the
Government had not offered him one.
In reply, Fields attached another plea agreement—not the
37-year offer described in his original motion—that, he
claimed, Skodinski had also received at some point during his
representation. The plea agreement attached to Fields’s reply
brief would have required Fields to plead guilty to all four
counts in the indictment with no sentence cap. Fields ex-
plained that he had attached this proposed plea agreement to
“discredit[] the Government[’ s]” argument that it had not ex-
tended any offers during Skodinski’s representation. But
Fields reiterated that his Ҥ 2255 motion raises a single, dis-
crete claim of ineffective assistance of counsel” based on
Skodinski’s failure “to adequately advise Fields regarding a
proposed plea agreement presented at jury selection,” i.e., the
37-year plea offer.
In response, the Government confirmed that it had no rec-
ord of either plea offer. Now focusing its arguments on the
plea offer attached to Fields’s reply brief, the Government
urged the district court to deny the § 2255 motion. The district
court did so, denying Fields’s § 2255 motion without conduct-
ing an evidentiary hearing. Like the Government, the district
judge’s analysis focused on the plea offer attached to Fields’s

6 No. 24-2913
reply brief. The district judge reasoned that Fields could not
show that declining this plea offer prejudiced him, because
his Sentencing Guidelines range would have been unchanged
and he did not show that it was probable that he would have
received a lower sentence if he had pleaded guilty.
Fields appealed, and we granted a certificate of appeala-
bility.
II. Discussion
Fields challenges the denial of his § 2255 motion without
an evidentiary hearing. “When reviewing the denial of a fed-
eral prisoner’s § 2255 petition, we review the district court’s
legal conclusions de novo, its factual findings for clear error,
and its decision to forgo holding an evidentiary hearing for
abuse of discretion.” Martin v. United States, 789 F.3d 703, 705
(7th Cir. 2015). An evidentiary hearing is “unnecessary” if
“‘the files and records of the case conclusively show that the
prisoner is entitled to no relief,’ or if the allegations are too
vague and conclusory.” Torres-Chavez v. United States, 828
F.3d 582, 586 (7th Cir. 2016) (quoting 28 U.S.C. § 2255(b)).
Fields claims that his attorney’s inadequate advice about a
plea offer violated his Sixth Amendment right to counsel. “It
has long been recognized that the right to counsel is the right
to the effective assistance of counsel.” McMann v. Richardson,
397 U.S. 759, 771 n.14 (1970). The Sixth Amendment right to
counsel extends to the plea-bargaining context, such that “[i]f
a plea bargain has been offered, a defendant has the right to
effective assistance of counsel in considering whether to ac-
cept it.” Lafler v. Cooper, 566 U.S. 156, 168 (2012); see Missouri
v. Frye, 566 U.S. 134, 140 (2012). To show ineffective assistance
of counsel, Fields must demonstrate that his counsel’s

No. 24-2913 7
performance was both deficient and prejudicial. Strickland v.
Washington, 466 U.S. 668, 687 (1984).
As a threshold matter, we must clarify which alleged plea
offer is at issue here. We agree with Fields that his claim is,
and always has been, predicated on the 37-year plea that he
claims to have received during jury selection. This is not a
hard call; Fields’s filings below and before us are clear. We
thus consider whether Fields may be entitled to relief on his
claim that Skodinski insufficiently advised him about that 37-
year plea offer.
In analyzing that claim, we will assume that Fields did, in
fact, receive a plea offer during jury selection and that Skodin-
ski advised him only that it was a “37-year plea.” And we will
further assume—although it is far from clear, legally—that
Skodinski’s failure to thoroughly review that offer was such
deficient performance that it fell below the Sixth Amendment
standard. See Frye, 566 U.S. at 149–50 (finding deficient per-
formance prong met where counsel failed to communicate
plea offer at all before it lapsed); Overstreet v. Wilson, 686 F.3d
404, 406–07 (7th Cir. 2012) (“Frye does not consider whether
counsel furnish ineffective assistance by failing to convey a
plea offer ‘effectively’; we assume without deciding that
counsel must do so.”); Mitchell v. United States, 846 F.3d 937,
939–40 (7th Cir. 2017) (same).
Even with the benefit of those assumptions, Fields must
establish prejudice under Strickland. To do so, Fields must
show that “(1) it is reasonably probable that but for the incom-
petent advice of his attorneys, he would have accepted the
government’s [] plea offer and pleaded guilty; and (2) it is rea-
sonably probable that the judge would have imposed a lower
sentence.” Day v. United States, 962 F.3d 987, 992 (7th Cir.

8 No. 24-2913
2020); see also Frye, 566 U.S. at 148.
Fields cannot make either of those showings. First, the rec-
ord is replete with contemporaneous evidence that, as his
lawyer put it, Fields “had no inclination for a plea agree-
ment.” Start with the preindictment plea offer that the Gov-
ernment first extended to Fields. In counseling Fields about
that offer, Hains explained that Fields risked an additional
three mandatory years of imprisonment if he declined the of-
fer and the Government obtained an indictment to a more se-
rious charge (discharging rather than brandishing a gun).
Fields declined, explaining (as memorialized in Hains’s
notes), “what makes a difference whether it is 30 years or 33
years, or 37 years,” since any of those were “a life sentence.”
Fields rejected later plea offers based on similar reasoning.
According to Hains, in considering a postindictment offer that
Fields “underst[ood]” would provide “the best deal possible”
at the time, Fields again declined, reasoning, “what’s the dif-
ference between twenty years and thirty years,” because “[i]n
essence, it’s a lifetime sentence because his mother will be
gone, his grandmother will be gone and his kids will be
grown.” Fields remained steadfast about rejecting any plea
offers despite Hains’s repeated warnings about “the likely
outcome of a trial.” “This consistent refusal to take a plea
agreement is evidence that [Fields] did not suffer prejudice
due to [his attorney’s] failure” to explain the 37-year offer. Fos-
ter v. United States, 735 F.3d 561, 567 (7th Cir. 2013).
Fields’s only evidence to the contrary is in a short declara-
tion accompanying his § 2255 motion, which contains vague
and internally contradictory statements. Fields asserts that
Skodinski “never explained to me that I could enter an ‘open’
guilty plea to the indictment which would avoid trial and

No. 24-2913 9
preserve my right to appeal the denial of my motion to sup-
press.” But that statement does not marry up with Fields’s le-
gal claim, which is predicated on the 37-year plea offer. The
37-year plea offer was not an “open guilty plea,” which is a
guilty plea “without the benefit of a plea agreement entered
into with the Government.” United States v. Mansfield, 21 F.4th
946, 951 n.2 (7th Cir. 2021) (citation omitted); see also, e.g.,
United States v. Turner, 55 F.4th 1135, 1140 (7th Cir. 2022). In-
stead, Fields describes the 37-year offer as a written agree-
ment, and a written agreement would have been necessary to
impose any type of 37-year sentencing cap. Adding to the in-
ternal contradictions here, an “open guilty plea” generally
would not have preserved Fields’s right to appeal the sup-
pression issue; preserving that type of appeal requires a spe-
cific concession from the Government. See F
ED. R. CRIM. P.
11(a)(2); Turner, 55 F.4th at 1139–42. Nor does Fields any-
where suggest that the 37-year plea offer preserved his right
to appeal the suppression issue, which was plainly important
to him.
Beyond his confusing assertion about an open guilty plea,
Fields generally claims that he “would have pled guilty” had
Skodinski “gone over the advantages” of doing so. But it is
undisputed that Fields knew the pros and cons of going to
trial from Hains. Fields has not explained why Skodinski’s
repetition of the same points would have made a difference,
nor does he connect this broad allegation to the specific 37-
year plea offer at issue here. As a result, Fields’s declaration
does not rebut the undisputed and detailed record evidence
that he would have refused any offer contemplating 37 years’
imprisonment.
Second, Fields also made no showing that, had he taken the

10 No. 24-2913
37-year plea offer, he would have received a lower sentence
than the 516-month (43-year ) sentence he is currently serving.
While the Government may promise to limit its own sentenc-
ing recommendation in a plea agreement, the parties may not
constrain a sentencing judge’s discretion without the judge’s
approval. See F
ED. R. CRIM. P. 11(c). Fields has not alleged that
the 37-year plea agreement would have bound his sentencing
judge, nor that the judge would have accepted it if so. And the
record points the other way: As the district judge considering
his § 2255 motion observed, “the nature of Mr. Fields’[s] of-
fense is alarming, and the Court’s view of his conduct would
remain the same whether Mr. Fields went to trial or accepted
a plea offer.”
Finally, it is also a problem for Fields that he successfully
appealed his § 924(c) conviction and benefited from a ten-year
sentencing reduction as a result. Had Fields pleaded guilty,
he would not have been able to pursue that claim on appeal.
See, e.g., Grzegorczyk v. United States, 997 F.3d 743, 747 (7th Cir.
2021) (“[Plaintiff]’s challenge to his § 924(c) conviction is the
exact type of claim we [have] deemed waived by an uncondi-
tional guilty plea.”). Given that wrinkle, it is particularly dif-
ficult for Fields to explain how he would be better off today
had he accepted the 37-year plea offer.
Thus even with a hefty thumb on the scale—assuming the
37-year plea offer existed, and that Skodinski’s advice about
it was so scanty as to fall below the constitutional floor—the
“files and records of the case” conclusively foreclose a finding
of Strickland prejudice. Torres-Chavez, 828 F.3d at 586 (citation
omitted). The district judge therefore did not abuse her dis-
cretion in denying Fields’s motion without an evidentiary
hearing.

No. 24-2913 11
* * *
The district court’s judgment is accordingly
AFFIRMED.