United States District Court, D. Minnesota
Douglas Earl Leiter, pro se.
PATRICK J. SCHILTZ UNITED STATES DISTRICT JUDGE
Douglas Leiter was convicted of tax-related offenses after a
jury trial at which he represented himself and relied mostly
on tax-protester arguments. Leiter was sentenced to 121
months in prison and three years of supervised release. ECF
No. 207. Leiter's conviction became final in September
2009, after his time to appeal expired. See Fletcher v.
United States, 858 F.3d 501, 504 (8th Cir. 2017). Leiter
did not challenge his conviction or sentence under 28 U.S.C.
§ 2255. Leiter was recently released from prison and is
now serving his three-year term of supervised release.
matter is before the Court on Leiter's motion under 18
U.S.C. § 3583 challenging most of the conditions of his
supervised release. Much of Leiter's motion is devoted to
arguing that the Court erred in rejecting his numerous
challenges to his criminal prosecution. Because Leiter's
conviction became final many years ago, however, it is far
too late for Leiter to make such arguments. See 28
U.S.C. § 2255(f) (imposing one-year statute of
limitations on challenges under § 2255); Fed. R. App. P.
4(b)(1)(A) (2009) (allowing ten days for a defendant to file
a notice of appeal in a criminal case). Even if it were not
too late, the Court would reject Leiter's arguments, as
they are as frivolous today as they were eight years ago.
his challenges to his supervised-release conditions, Leiter
contends that they are only now ripe for review because, at
the time that he filed his motion, his release (and therefore
the enforcement of those conditions) was imminent. The Court
recognizes that some support for Leiter's argument can be
found in United States v. Thomas, 198 F.3d 1063 (8th
Cir. 1999). The Court nevertheless holds that Leiter's
challenges are untimely.
Thomas, the defendant argued on direct appeal that a
condition of his supervised release was unconstitutionally
vague and fundamentally unfair. Id. at 1065. The
Eighth Circuit declined to entertain the defendant's
challenge, finding that it was premature. Id. The
court reasoned that, during the defendant's nearly
ten-year prison sentence, “any number of events may
occur that would make the condition irrelevant.”
Id. Thus, the court concluded, “[u]ntil such
time as the condition's enforcement is imminent, the
dispute is only abstract.” Id. The court went
on to note that the defendant could move to modify the
conditions and, if the defendant's supervised release
were later revoked, he would have “the opportunity for
appellate review at that time.” Id.
therefore could be read to suggest that at least some of
Leiter's challenges to his supervised-release conditions
are timely. For several reasons, however, the Court
respectfully declines to follow Thomas:
and most importantly, Thomas is inconsistent with
numerous cases involving lengthy prison sentences in which
the Eighth Circuit considered, on direct appeal, challenges
that were materially indistinguishable from those raised in
Thomas. See, e.g., United States v.
Deatherage, 682 F.3d 755 (8th Cir. 2012) (defendant
sentenced to 70 months allowed on direct appeal to raise
First Amendment challenge to conditions); United States
v. Schaefer, 675 F.3d 1122 (8th Cir. 2012) (defendant
sentenced to 97 months allowed on direct appeal to challenge
conditions on ground that they infringed his constitutionally
protected relationship with his children); United States
v. Stults, 575 F.3d 834 (8th Cir. 2009) (defendant
sentenced to 144 months allowed on direct appeal to challenge
condition as unconstitutionally vague); United States v.
Choate, 101 F.3d 562 (8th Cir. 1996) (defendant
sentenced to 38 months allowed on direct appeal to challenge
condition as overly broad); United States v. Smith,
972 F.2d 960 (8th Cir. 1992) (defendant sentenced to 51
months allowed on direct appeal to challenge condition of
supervised release as infringing his right to father
Thomas is in considerable tension with the fact that
district courts are charged with making an individualized
inquiry into the reasonableness and necessity of each
condition of supervised release at the time of sentencing.
See Schaefer, 675 F.3d at 1124.
Thomas's concern with avoiding
“abstract” questions therefore seems misplaced;
if a district court is obligated to make certain that a
condition of supervised release is valid at the time it
is imposed, why would an appellate court not have the
same obligation on direct appeal? The issue is no more
“abstract” for the appellate court than it is for
the district court.
the fact that circumstances might change while a defendant is
in prison is a particularly odd basis on which to hold that a
purely legal challenge of the type raised in Thomas
is premature. Thomas's vagueness challenge-that is, an
argument that a condition of supervised release was invalid
on its face-is not affected by the passage of time.
That challenge was, in fact, more concrete and
amenable to decision on direct appeal than, say, an argument
that a condition of supervised release is more restrictive
than necessary under the circumstances. Yet the Eighth
Circuit routinely considers the latter type of challenge on
direct appeal, even in cases involving lengthy sentences.
See, e.g., Stults, 575 F.3d at 850
(defendant sentenced to 144 months allowed, on direct appeal,
to challenge four conditions of supervised release on the
ground that they constituted a greater deprivation of liberty
Thomas makes it difficult to know how and when a
defendant is supposed to challenge a condition of supervised
release. As noted, Thomas seemed to suggest that the
defendant's “opportunity for appellate
review” would be after a revocation proceeding.
Thomas, 198 F.3d at 1065. But in United States
v. Miller, 557 F.3d 910 (8th Cir. 2009)-a decision
issued ten years after Thomas-the Eighth Circuit
held that a defendant cannot challenge the validity
of his supervised-release conditions in a revocation
proceeding and further noted that such challenges should be
raised on direct appeal or in a “habeas corpus
proceeding.” Id. at 913. The Miller
panel was apparently unaware that the Thomas panel
had already held that such challenges cannot, in fact, be
raised on direct appeal-at least where the defendant has
received a lengthy prison sentence. Likewise, a motion under 28
U.S.C. § 2255 is unlikely to be a suitable vehicle for
challenging supervised-release conditions in cases involving
even modestly long prison sentences. The applicable statute
of limitations will normally dictate that such motions be
brought at a time when the defendant's challenge would
presumably still be considered premature under
Thomas. Oddly, then, a motion under 18 U.S.C. §
3583(e)(2)-a provision permitting courts to “modify,
reduce, or enlarge the conditions of supervised
release”-appears to be the only way for a defendant to
challenge the legality of a condition of supervised release,
at least when the defendant has been sentenced to a long
prison term. The Court has difficulty believing that the
Eighth Circuit intended such a result.
of these reasons, then, the Court concludes that
Thomas is inconsistent with Eighth Circuit
precedent-including precedent that predates it-and therefore
declines to follow the decision. See Mader v. United
States, 654 F.3d 794, 800 (8th Cir. 2011) (en banc)
(when panel opinions conflict, the earlier of the opinions
must be followed, as it should have controlled the subsequent
panels). Leiter should have challenged the validity of his
supervised-release conditions on appeal or by way of a §
2255 motion. It is too late for Leiter to challenge those
conditions now, eight years after they were imposed.
Leiter's challenges were timely, however, the Court would
reject them on the merits:
Leiter challenges several conditions on the ground that they
violate the Fourth Amendment's prohibition on
unreasonable searches. Defendants under supervision have a
diminished expectation of privacy, however, and suspicionless
searches are generally permissible so long as the defendant
had notice that he was subject to such searches. See
United States v. Jackson, 866 F.3d 982, 985 (8th Cir.
2017) (“Given Jackson's diminished expectation of
privacy as a supervised releasee, and the clear notice that
his cell ...