Chad Douglas Dressen v. United States of America

United States Court of Appeals
For the Eighth Circuit
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No. 20-2846
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Chad Douglas Dressen
Plaintiff - Appellant
v.
United States of America
Defendant - Appellee
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Appeal from United States District Court
for the District of South Dakota - Southern
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Submitted: October 22, 2021
Filed: March 18, 2022
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Before COLLOTON, SHEPHERD, and KELLY, Circuit Judges.
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KELLY, Circuit Judge.
Chad Dressen filed a motion to vacate, set aside, or correct his sentence
pursuant to 28 U.S.C. § 2255, asserting among other things that he received

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ineffective assistance of counsel. The district court1 dismissed most of his claims
but granted a certificate of appealability on whether Dressen’s attorney failed to file
a direct appeal despite instructions to do so. Having jurisdiction pursuant to 28
U.S.C. §§ 1291 and 2253(a), we affirm.
I.
In 2017, Dressen was charged with one count of conspiracy to distribute 50
grams or more of methamphetamine in violation of 21 U.S.C. §§ 841(a) and 846,
and he retained D. Sonny Walter to represent him. Dressen pleaded guilty pursuant
to a plea agreement, which contained a limited waiver of appeal. The conviction
carried a 10-year mandatory minimum sentence and a maximum of life
imprisonment. Dressen also agreed to cooperate fully with the government. In
exchange, the government agreed that it would evaluate his cooperation and consider
filing a motion pursuant to Federal Rule of Criminal Procedure 35(b) to reduce his
sentence. In May 2018, the district court sentenced Dressen to 210 months of
imprisonment, at the bottom of his advisory United States Sentencing Guidelines
range of 210–262 months. In November 2019, the government filed a Rule 35(b)
motion, and Dressen’s sentence was reduced to 105 months.
On November 16, 2018, Dressen filed a motion to vacate under § 2255. He
asserted several claims, including ineffective assistance of counsel and errors in the
calculation of his Guidelines range. The district court granted the government’s
motion to dismiss all claims except one: whether counsel was ineffective for failing
to file a notice of appeal after Dressen asked him to. The court directed the
magistrate judge to conduct an evidentiary hearing on this claim and to appoint
counsel to represent Dressen.
1 The Honorable Karen E. Schreier, United States District Judge for the
District of South Dakota, adopting the report and recommendation of the Honorable
Veronica L. Duffy, United States Magistrate Judge for the District of South Dakota.

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The magistrate judge held an evidentiary hearing on February 26, 2020.
Dressen, Walter, and Teresa Hanson,2 Dressen’s girlfriend, all testified.
Dressen testified that he “signed for a 10-year plea” but just two days before
sentencing, Walter told him that, unless he agreed to a 17-year sentence, he would
receive a sentence of 25 years in prison. After sentencing, Dressen, Hanson, and
Walter went into the hallway, where Dressen told Walter, “[W]e have to appeal this.”
Dressen said that “there was no other choice but to appeal” because his sentence was
twice as long as he anticipated.
According to Dressen, Walter responded that he had to “wait on some
paperwork” before filing the appeal. Dressen was taken into custody after
sentencing, so he asked Hanson to contact Walter about the appeal. It was not until
he was transferred to an out-of-state facility a few months later that Dressen learned
that a notice of appeal had not been filed. Dressen also testified that prior to the
hallway conversation and before pleading guilty, he and Walter never “discussed an
appeal” or talked about whether he had waived his right to appeal. On cross-
examination, Dressen admitted that, before the evidentiary hearing, he and Hanson
had discussed their anticipated testimony.
Hanson testified next. She said she contacted Walter a few days before
sentencing to ask about the “sudden” change in “the amount of time Chad was going
to get.” According to Hanson, Walter told her it was “what we had to do” and that
“the appeal process would start as soon as [Dressen] was sentenced.” Like Dressen,
she said they met in the hallway after sentencing and that Walter “reassured [them]
that he would start appealing.” Although she did not recall exactly what was said,
she testified that Walter told them he “would start that process immediately.”
2 Teresa also went by the last name “Haugan” at times.

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Later, Hanson learned from Dressen that the notice of appeal had not been
filed. She tried to contact Walter, wanting to ask him why and to get copies of some
paperwork. Contrary to Dressen’s testimony, Hanson said that she and Dressen did
not speak about their testimony before the hearing.
Walter was the last witness to testify. Walter has practiced law since 1989,
specializing in criminal defense and prisoner litigation. Walter explained that when
clients are not immediately taken into custody after sentencing, he speaks with them
for a bit in the courthouse hallway. He “presume[d]” he did this with Dressen. He
said that “if Mr. Dressen would have asked [him] to put in an appeal, [he] would
have noted that on [his] file” and would have calendared the deadline in his phone
and in his “analog calendar” as back-up, as is his habit since he works alone.
Although he did not “have an independent recollection” of the conversation that
occurred after Dressen’s sentencing, he stated that any such appeal request “would
have been a significant event.” And he reiterated that “[i]f [Dressen] had asked for
an appeal, [he’d] recall it” and “would have had a serious discussion” with Dressen
about it because he did not believe there were any appealable issues. Walter testified
that he did, however, calendar the deadline to remind the government to file a Rule
35(b) motion. Finally, Walter stated that he reviewed his phone records—including
texts and calls—and found that there was nothing from Hanson prior to the appeal
deadline indicating that Dressen wanted to file an appeal.
At the conclusion of the hearing, the magistrate judge found Walter’s
testimony credible and Dressen’s and Hanson’s testimony less so, and recommended
that Dressen’s remaining claim be dismissed. Over Dressen’s objections, the district
court adopted that recommendation.
The district court provided several reasons for crediting Walter’s testimony
that neither Dressen nor Hanson asked him to file a notice of appeal. The court
pointed to Walter’s lengthy legal career, including experience assisting inmates with
filing appeals and habeas petitions, and noted that an attorney with such a
background would know the importance of filing a notice of appeal when a client

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requests one. The court also cited Walter’s testimony about his normal practice of
calendaring deadlines and the fact that Walter recorded other deadlines for Dressen’s
case but not an appeal deadline. And the district court reasoned that, because Walter
knew Dressen had signed an appeal waiver, it would have been a “memorable event”
if Dressen had asked him to file a notice of appeal, as this would have necessitated
a conversation with his client about why an appeal was unlikely to succeed.3
In contrast, the court concluded that Dressen and Hanson were less credible
witnesses. The court found that Dressen’s credibility was undermined by his failure
to include facts in support of his failure-to-appeal claim until his testimony at the
evidentiary hearing. This was true even though his motion and previous filings were
replete with facts to support the other claims he raised. The court also highlighted
the discrepancies between Dressen’s and Hanson’s testimony, including the fact that
Hanson denied any discussions with Dressen about their testimony before the
hearing. The court found this cast doubt on Hanson’s credibility and called into
question her motives for testifying.
II.
“We review for clear error the district court’s findings of fact following an
evidentiary hearing held on a § 2255 motion.” Fiorito v. United States, 821 F.3d
999, 1003 (8th Cir. 2016). We review de novo the district court’s ultimate
3 Dressen argues that the court should not place any weight on Walter’s
testimony that he would have had a “serious discussion” with Dressen about a
possible appeal because it goes to the merits of the appeal. But that misses the point.
The district court found this testimony undermined Dressen’s assertion that he
requested an appeal because—if he had requested one—it would have been a
“memorable event for Walter” for a number of reasons, one of which was the
necessary and serious discussion he would have had with Dressen. In other words,
the district court relied on the existence of the appeal waiver and Walter’s testimony
to assess the credibility of Dressen’s assertion that he had requested an appeal, not
to assess the merits of an appeal had Dressen actually requested one.

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conclusion on whether the defendant received ineffective assistance of counsel.
Walker v. United States, 810 F.3d 568, 575 (8th Cir. 2016).
Typically, to prevail on an ineffective assistance of counsel claim, a defendant
must show that his counsel’s performance was deficient—meaning that it “fell below
an objective standard of reasonableness”—and that the deficiency prejudiced his
defense. Dat v. United States, 920 F.3d 1192, 1193 (8th Cir. 2019) (quoting Jae Lee
v. United States, 137 S. Ct. 1958, 1964 (2017)). However, when “an attorney
disregards specific instructions from a defendant to file a notice of appeal, he ‘acts
in a manner that is professionally unreasonable.’” Watson v. United States, 493 F.3d
960, 963 (8th Cir. 2007) (quoting Roe v. Flores-Ortega, 528 U.S. 470, 477 (2000)).
In such a case, “prejudice is presumed because the defendant has forfeited his right
to an appellate proceeding as a result of his counsel’s error.” Id. at 963–64; see also
id. at 964 (“The court need not inquire into whether the intended appeal would be
meritorious or likely to succeed.”).
“A bare assertion by the petitioner that [he] made a request is not by itself
sufficient to support a grant of relief, if evidence that the fact-finder finds to be more
credible indicates the contrary proposition.” Barger v. United States, 204 F.3d 1180,
1182 (8th Cir. 2000). Where a defendant and his attorney submit conflicting
affidavits about the existence of such instructions, the court must conduct an
evidentiary hearing to assess which witness is more credible. See Witthar v. United
States, 793 F.3d 920, 924 (8th Cir. 2015). After such a hearing, this court accords
great deference to the district court’s credibility determinations. United States v.
Harper, 787 F.3d 910, 914 (8th Cir. 2015) (“Credibility assessments are ‘the
province of the trial court.’” (quoting United States v. Heath, 58 F.3d 1271, 1275
(8th Cir. 1995))). “[T]he ‘decision to credit a witness’s testimony over that of
another can almost never be a clear error unless there is extrinsic evidence that
contradicts the witness’s story or the story is so internally inconsistent or implausible
on its face that a reasonable fact-finder would not credit it.’” Id. (quoting Heath, 58
F.3d at 1275).

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Dressen argues that the district court’s credibility findings were in error.
Dressen emphasizes that both he and Hanson testified in detail regarding the events
that occurred immediately after sentencing and were able to recite where the
conversation with Walter took place and what was said. And both recalled leaving
the meeting with the understanding that Walter was going to file a notice of appeal.
In contrast, Walter admitted that he did not have a specific recollection of his
conversation with Dressen. Instead, Walter testified to what he presumed would
have happened based on his typical course of conduct in similar situations.
The district court’s factual finding—that Dressen did not direct Walter to file
a notice of appeal within 14 days of sentencing—was based on a reasonable
credibility determination, and we see no clear error. See Barger, 204 F.3d at 1182
(“Credibility findings are for the trier of fact, . . . and we cannot say that the district
court’s findings regarding counsel’s credibility are clearly erroneous.”). Of the three
witnesses, the court found Walter the most credible, persuaded by his habit of
calendaring deadlines, his understanding of the importance of filing a timely notice
of appeal, and his view that a request from Dressen to file an appeal would have
been “memorable” under the circumstances.
Dressen testified otherwise, asserting he told Walter he wanted to appeal. But
the district court found that Dressen’s failure to allege any factual details to support
this claim in his original § 2255 motion (or at any time prior to the hearing)
undermined his credibility. And the court expressed doubt about the value of
Hanson’s testimony at all. The district court considered Dressen’s allegation that he
instructed Walter to file a notice of appeal but found it to be a “bare assertion”
without credible evidentiary support. See id. On this record, we find no clear error
in the finding that Dressen did not instruct his attorney to file a notice of appeal
within the deadline for doing so. See Green v. United States, 323 F.3d 1100, 1102–
03 (8th Cir. 2003) (finding no clear error in district court’s determination that
defendant’s testimony that he requested an appeal was not credible).

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III.
The judgment of the district court is affirmed.
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