 United States Court of Appeals
         FOR THE DISTRICT OF COLUMBIA CIRCUIT



Argued September 14, 2012         Decided October 19, 2012

                       No. 07-3054

               UNITED STATES OF AMERICA,
                       APPELLEE

                             v.

                    GREGORY TERRELL,
                       APPELLANT


        Appeal from the United States District Court
                for the District of Columbia
                     (No. 03cr00207-01)


     Sandra G. Roland, Assistant Federal Public Defender,
argued the cause for appellant. With her on the briefs was
A.J. Kramer, Federal Public Defender. Neil H. Jaffee and
Lisa B. Wright, Assistant Federal Public Defenders, entered
appearances.

    Katherine M. Kelley, Assistant U.S. Attorney, argued the
cause for appellee. With her on the brief were Ronald C.
Machen Jr., U.S. Attorney, and Roy W. McLeese III and Mary
B. McCord, Assistant U.S. Attorneys. Elizabeth Trosman,
Assistant U.S. Attorney, entered an appearance.
                               2

    Before: SENTELLE, Chief Judge, GRIFFITH, Circuit Judge,
and WILLIAMS, Senior Circuit Judge.

   Opinion for the Court filed by Senior Circuit Judge
WILLIAMS.

     WILLIAMS, Senior Circuit Judge: Appellant Gregory
Terrell pleaded guilty to unlawful possession with intent to
distribute five grams or more of cocaine base in violation of
21 U.S.C. §§ 841(a)(1) and (b)(1)(B)(iii). On April 24, 2007,
the district court sentenced him to 210 months of
imprisonment, five years of supervised release, and a $100
special assessment. Terrell challenges that sentence on two
primary grounds. First, he argues that it violates the ex post
facto clause of the Constitution because the United States
Sentencing Guidelines Manual applied by the district court
was promulgated after he committed the offense of conviction
and may have resulted in a harsher sentence than the one
yielded by the Manual in effect at the time of offense.
Second, he contends that the district court had an erroneously
limited view of its discretion to impose a below-Guidelines
sentence following the Supreme Court’s decision in United
States v. Booker, 543 U.S. 220 (2005).

     Although we reject Terrell’s ex post facto argument, we
are persuaded by his claim as to the district court’s concept of
its discretion, and therefore vacate the sentence and remand
for resentencing.


                            * * *

    Because Terrell failed to raise either of his arguments
before the district court, we review his claims for plain error.
Of the canonical statement’s four requirements for plain error,
the first two are that there be error and that it be “plain.”
United States v. Olano, 507 U.S. 725, 732 (1993). In its role
                                3

as the second requirement, “plain” simply means “clear.”
United States v. Williams-Davis, 90 F.3d 490, 507 (D.C. Cir.
1996). A ruling’s error is clear if, at the time it was made, a
clear precedent in the Supreme Court or this circuit
established its erroneous character. See, e.g., United States v.
Mouling, 557 F.3d 658, 664 (D.C. Cir. 2009).

     Ex post facto claim.         This contention is fatally
undermined by the absence of any clear precedent at the time
of sentencing. At all times relevant to this appeal, the
Sentencing Guidelines directed courts generally to “use the
Guidelines Manual in effect on the date that the defendant is
sentenced.” USSG § 1B1.11(a). But if application of that
mandate would violate the ex post facto clause, a court must
apply the Guidelines Manual that was “in effect on the date
that the offense of conviction was committed.”              Id.
§ 1B1.11(b)(1). Application of a post-offense Guidelines
Manual violates the ex post facto clause if there is a
substantial risk that it will result in a more severe sentence
than the defendant would have received under the Manual that
was in effect when he committed the offense. See United
States v. Turner, 548 F.3d 1094, 1100 (D.C. Cir. 2008).

    Terrell committed his offense in April 2003, when the
2002 Guidelines Manual was in effect. At the sentencing in
2007, the district court started its analytical process with the
pre-sentence report, which had been drafted under the 2005
Guidelines Manual. (By the time of sentencing, the 2006
Guidelines had become applicable, but on the issue in
question there was no difference between the 2005 and 2006
versions.) Terrell argues that there is a substantial risk that he
received a harsher sentence under the 2005 Manual than he
would have received under the 2002 version.

    His contention is based on an amendment to § 3E1.1, the
Guidelines provision that governs adjustments in offense level
                               4

for acceptance of responsibility. At all relevant times,
§ 3E1.1(a) directed a sentencing court to reduce a defendant’s
offense level by two levels if he “clearly demonstrates
acceptance of responsibility for his offense.” But the second
part of the provision—§ 3E1.1(b)—was amended after Terrell
committed the offense. At the time of offense, § 3E1.1(b)
directed the district court to reduce a defendant’s offense level
by one additional level—that is, to award a “third point” for
acceptance of responsibility—if the initial offense level was
16 or higher and the defendant “assisted authorities in the
investigation or prosecution of his own misconduct” either by
timely providing complete information regarding his
involvement or by timely notifying authorities of his intention
to plead guilty. With the amendment, which went into effect
on April 30, 2003, § 3E1.1(b)’s “third point” became
available only “upon motion of the government.”

     During Terrell’s sentencing proceedings, the judge
expressed a desire to award the third point. He asked the
attorneys and the probation officer who attended the hearing
whether he had discretion to do so sua sponte. Tr. 3/27/07, at
20:2-4. Based on their responses, he concluded that he did
not, id. at 22:13-16, which was correct under the amended
version of § 3E1.1(b) but not under the version in the 2002
Manual. The district court then asked the government to
move for the third point, explaining that “188 months is just
as serious as 210 months. I mean, there’s a numerical
difference, but in the scheme of things in the real world
there’s not a heck of a lot of difference.” Id. at 23:11-15.
Counsel for the government refused to move for the third
point, arguing that Terrell had not provided authorities with
the requisite assistance. Id. at 25:7-10. Because the district
court believed it could not award the third point
independently, Terrell received only a two-point reduction in
his offense level for acceptance of responsibility. The district
                               5

court sentenced him at the low end of the resulting Guidelines
range.

     Terrell argues that the ex post facto clause required the
district court to apply the 2002 Guidelines Manual. Under it,
the judge had full discretion to award (and, Terrell contends,
likely would have awarded) the third point. That would have
reduced Terrell’s offense level by an additional step,
decreasing his Guidelines range. But assuming the soundness
of that claim, we believe that any error in non-application of
the 2002 Manual was not a clear error. (For that reason, we
need not reach the government’s arguments that Terrell’s plea
agreement bars his claim and that application of the 2005
Manual didn’t violate the ex post facto clause.)

     After Booker rendered the Guidelines advisory in 2005,
courts disagreed about whether applying a post-offense
Guidelines Manual that yielded a higher sentencing range
would continue to violate the ex post facto clause. Compare,
e.g., United States v. Demaree, 459 F.3d 791, 795 (7th Cir.
2006) (holding that the ex post facto clause “should apply
only to laws and regulations that bind rather than advise”),
with, e.g., United States v. Carter, 490 F.3d 641, 643 (8th Cir.
2007) (holding that after Booker the ex post facto clause
continued to apply to adverse Guidelines changes). Neither
this court nor the Supreme Court had decided the issue when
Terrell was sentenced. See United States v. Andrews, 532
F.3d 900, 909 (D.C. Cir. 2008) (noting—more than a year
after Terrell’s sentencing—that “[t]his circuit has not yet
determined whether, after Booker, application of a later (than
the date-of-offense) Guidelines Manual that yields a higher
sentence continues to raise an ex post facto problem”). The
issue remained unresolved until our decision in Turner, 548
F.3d at 1099-1100, holding that the ex post facto clause would
apply notwithstanding Booker.
                               6

     Because the law was unsettled when Terrell was
sentenced, the district court’s failure to apply the 2002
Manual did not constitute plain error, assuming it was error at
all. See Mouling, 557 F.3d at 664. Booker had unsettled the
law, and neither the Supreme Court nor this court had yet
resettled it.

      Scope of sentencing discretion. On February 13, 2007,
less than three months before Terrell was sentenced, we
rejected the idea that the Guideline range should be
considered presumptively reasonable.         United States v.
Pickett, 475 F.3d 1347, 1353 (D.C. Cir. 2007). We held in
Pickett that “[a] sentencing judge cannot simply presume that
a Guidelines sentence is the correct sentence.” Id. Instead,
we said that with respect to each individual defendant, the
court must “evaluate how well the applicable Guideline
effectuates the purposes of sentencing enumerated in [18
U.S.C.] § 3553(a).” Id. The Supreme Court endorsed the
same rule shortly after Terrell was sentenced. See Rita v.
United States, 551 U.S. 338, 351 (2007) (holding that a
“sentencing court does not enjoy the benefit of a legal
presumption that the Guidelines sentence should apply,”
although a within-Guidelines sentence may be presumed
reasonable on appeal); Gall v. United States, 552 U.S. 38, 49-
50 (2007) (reiterating Rita’s holding that a sentencing judge
“may not presume that the Guidelines range is reasonable”).
(In United States v. Anderson, 632 F.3d 1264, 1269 (D.C. Cir.
2011), we noted that the Supreme Court made this rule clear
in Rita, but we said nothing about Pickett. Whether the rule
for our circuit was first clearly established in Rita or Pickett
was of no consequence in Anderson, but it is here. Pickett
first established this rule in our circuit.)

    Statements that the district court made in this case
suggest that, notwithstanding Pickett, the court took too
narrow a view of its authority to deviate from the Guidelines.
                                7

Throughout the proceedings, the court stated that it would
sentence Terrell below the applicable Guidelines range only if
it found “compelling reasons” to do so. See, e.g., Tr. 6/27/06,
at 4:6-14 (“There would have to be compelling reasons for the
Court not [to] impose an advisory guideline sentence.”); id. at
7:8, 7:18-20 (“Now, I’m not so sure compelling reasons exist
here. . . . [I]f you think there’s a basis for the Court to impose
something other than an advisory guideline sentence it’s going
to have to be for compelling reasons.”); see also Tr. 8/4/05, at
4:16-18 (“In all likelihood, I’m going to follow the guidelines
even though they’re advisory. In all likelihood I’m going to
do that.”). The court explained that it had found “compelling
reasons” to deviate from the Guidelines in only two prior
sentencings. Tr. 6/27/06, at 4:6-14. Even after we issued our
decision in Pickett, the court indicated that it was continuing
to apply its “compelling reasons” approach. See Tr. 3/27/07,
at 10:2-3 (“The question becomes why shouldn’t the Court
impose a [within-Guidelines] sentence of 210 months? . . . I
just can’t think of any compelling reasons why I should not
impose a sentence of 210 months.”).

    The district court’s “compelling reasons” rule is
functionally equivalent to a presumption that the Guidelines
range is reasonable, blocking a non-Guidelines sentence in the
absence of special, “compelling” circumstances. See, e.g.,
United States v. Alexander, 556 F.3d 890, 893 (8th Cir. 2009);
United States v. King, 541 F.3d 1143, 1145 (5th Cir. 2008).
Pickett had clearly forbidden that approach prior to Terrell’s
sentencing.

    The government argues nonetheless that the district court
committed no error. As the government notes, the district
court stated repeatedly that the Guidelines were merely
advisory and that it would refer to the § 3553 factors in
determining Terrell’s sentence. See, e.g., Tr. 6/27/06, at 3:8-
10; Tr. 4/24/07, at 15:14, 18:12-14. Moreover, it was clearly
                                8

aware of Terrell’s individual circumstances and took those
circumstances into account in crafting his sentence. But
neither of these observations defeats Terrell’s claim. A judge
might well recognize that he is not bound by the Guidelines
but nonetheless believe (erroneously) that the Guidelines are
presumptively reasonable. Likewise, a judge might have a
deep understanding of a defendant’s background but
nonetheless believe (again erroneously) that he must pick out
some especially “compelling” circumstance from that
background in order to deviate from the Guidelines range.
The district court’s approach in this case plainly contravened
Pickett, and the government’s arguments do not convince us
otherwise.

     Having determined that the district court committed an
error that was clear at the time of sentencing, we must
consider whether Terrell has shown the other two elements
that are required for him to prevail—the requirements that the
error affects “substantial rights” and “seriously affects the
fairness, integrity or public reputation of judicial
proceedings.” Olano, 507 U.S. at 732 (citations, internal
quotation marks, and brackets omitted). To show that an error
affected substantial rights, a defendant must demonstrate “a
reasonable likelihood” that the error affected the outcome,
United States v. Gomez, 431 F.3d 818, 822 (D.C. Cir. 2005),
and in the sentencing context that probabilistic showing is
“slightly less exacting” than that required for trial errors,
United States v. Saro, 24 F.3d 283, 287-88 (D.C. Cir. 1994).
Finally, as to the fourth element, we have held that because
“keeping [a] defendant in prison longer for improper reasons”
affects the fairness, integrity, and public reputation of judicial
proceedings, we should ordinarily exercise our discretion to
correct a clear error that causes such a result. In re Sealed
Case, 573 F.3d 844, 852-53 (D.C. Cir. 2009).
                                9

     We think the defendant has shown a reasonable
likelihood that he would have received a shorter sentence but
for the district court’s error. Throughout the proceedings, the
district court took actions with the apparent hope of lowering
Terrell’s Guidelines range. For example, the judge delayed
the proceedings so as to allow Terrell a chance to obtain a
reduced sentence by cooperating with the government, see Tr.
6/27/06, at 11:2-24, and to see whether Pickett’s holding as to
the crack/powder cocaine sentencing disparity would provide
a basis for reducing the sentence, see Tr. 11/28/06. And most
strikingly, as noted above, the judge asked the government to
award Terrell a third point for acceptance of responsibility,
arguing that 188 months of imprisonment—the low end of the
Guidelines range that would apply if Terrell received the third
point—was “just as serious as” 210 months of imprisonment
(presumably in terms of satisfying the sentencing purposes
laid out in § 3553(a)). Tr. 3/27/07, at 20-23.

     The government contends that the record as a whole
precludes a finding of prejudice. Indeed, some of the district
court’s statements at sentencing suggest that the judge
believed a 210-month sentence was appropriate without
reference to any “compelling reasons” requirement. See, e.g.,
Tr. 4/24/07, at 15:12-17 (explaining that Terrell “seems . . . to
fit the profile of the career offender regulations . . . and,
accordingly, should be sentenced to that voluntarily [sic]
guideline range unless there are some 3553 factors or other
factors to take it out of that category, but I’m at a lost [sic] to
find . . . just what those other factor[s] are”).

    Those contradictions in the record do not defeat Terrell’s
claim, however. Because the error is one of sentencing,
Terrell need only meet the “somewhat lighter” burden of
showing prejudice. Saro, 24 F.3d at 288. The district court
made serious efforts to find a route to a reduced Guidelines
range, all of which failed. It could have achieved exactly the
                               10

same result by sentencing Terrell below the Guidelines—and
under a correct understanding of the law, nothing barred it
from doing so. (The district court’s statement that a 188-
month sentence was “just as serious” as a 210-month sentence
also calls into question whether the court believed the 210-
month sentence it ultimately imposed was truly “sufficient,
but not greater than necessary,” to achieve the goals of
sentencing, as required by 18 U.S.C. § 3553(a).)

     Because Terrell has shown a reasonable likelihood that
the district court’s plain error lengthened his sentence, we also
conclude that the error seriously affected the fairness,
integrity, or public reputation of judicial proceedings. See In
re Sealed Case, 573 F.3d at 852-53. Terrell has established
all of the elements required for reversal on plain error review,
and we therefore conclude that he is entitled to resentencing.


                             * * *

    The judgment is vacated and the case remanded for
resentencing.

                                                   So ordered.
