In the
 United States Court of Appeals
              For the Seventh Circuit
                       ____________

No. 06-4373
UNITED STATES OF AMERICA,
                                           Plaintiff-Appellee,
                             v.

RAYMOND RYALS,
                                       Defendant-Appellant.
                       ____________
         Appeal from the United States District Court
            for the Western District of Wisconsin.
          No. 06-CR-99-S—John C. Shabaz, Judge.
                       ____________
  ARGUED OCTOBER 22, 2007—DECIDED JANUARY 10, 2008
                   ____________


 Before KANNE, EVANS, and WILLIAMS, Circuit Judges.
  WILLIAMS, Circuit Judge. Raymond Ryals received a
staggering 365-month prison sentence for brokering the
sale of an ounce of crack cocaine—a job that earned him
$50. The sole issue in this direct criminal appeal is
whether the district court abused its discretion by re-
fusing to appoint Ryals new counsel for his sentencing
hearing. The motion for new counsel was timely, but the
district court did not make an adequate inquiry into the
breakdown in communication between Ryals and his
lawyer. We therefore conclude that the district court
abused its discretion and remand the case for
resentencing.
2                                                No. 06-4373

                     I. BACKGROUND
  The drug deal that led to Ryals’s arrest and prosecution
was straightforward. Police officers in Beloit, Wisconsin
directed a confidential informant to wear a wire and buy
an “onion” of crack from Ryals (an onion is an ounce).
Ryals recommended a seller to the CI, the CI agreed and
paid Ryals, and Ryals obtained and delivered the crack.
Ryals was charged with distributing cocaine base, 21
U.S.C. § 841(a)(1), and a jury found him guilty after a one-
day trial.
   No indication of Ryals’s dissatisfaction with his ap-
pointed counsel came out until about two months after
he was convicted. At that time he and his attorney reached
an impasse over how to handle his sentencing hearing,
which was three weeks away. Ryals wanted to raise a
number of sentencing issues, but counsel refused and
filed no objection to the presentence investigation report.
Ryals then instructed his lawyer to file a motion to
withdraw. The motion was brief, and summed up: “Mr.
Ryals informed me that he wishes to seek other counsel to
represent him at sentencing.” For reasons that are not
clear to us, the district court did not take up the motion
until the sentencing hearing.
  At that hearing the district court first heard from
counsel, who stated that Ryals “informed me that he
thought that I made certain choices during the course of
his trial which were inappropriate. He has indicated to
me that he does not have any confidence in me as a
counsel . . . the long and the short of it, Your Honor, is that
he didn’t want me to have anything to do with his case
from that point on.” The district judge asked whether
counsel was familiar with the file, and counsel said yes.
The judge asked whether counsel was “able to adequately
represent this defendant at sentencing this afternoon,” and
counsel said no: “I say no, Your Honor, because I know
expressly that he doesn’t want me to represent him.”
No. 06-4373                                                  3

   Rather than follow up on this statement, the court
then turned to Ryals, who said, “I don’t want him repre-
senting me,” because “he didn’t do a lot of things and he
done [sic] a lot of things and let a lot of things be done that
I would like to be looked into.” Despite these assertions
from counsel and from Ryals, the court then concluded that
“[counsel] is prepared to proceed regardless of his com-
ments to the contrary,” because counsel had rendered
adequate assistance at trial, and because there was
little that another lawyer could do given the posture of
the case. The court then heard Ryals himself make sev-
eral sentencing arguments—most of which were chal-
lenges to his criminal history points—allowed the gov-
ernment to explain their lack of merit, and imposed
sentence. When given the chance to speak on his own
behalf before the sentence was imposed, Ryals said, “there
was [sic] a lot of things that I think I need to talk to
another attorney about that went on in this and went on at
trial, Your Honor. I mean, and if I proceed with sentencing
I would like to just proceed without an attorney at all.”
The court replied that Ryals could have a new attorney on
appeal.


II. ANALYSIS—DISTRICT COURT ABUSED DISCRETION
      BY DENYING MOTION FOR NEW COUNSEL

  In analyzing whether the district court abused its
discretion in denying Ryals’s motion for new counsel, we
consider several factors, including (1) the timeliness of the
motion; (2) whether the district court conducted an
adequate inquiry into the matter; and (3) whether the
breakdown between lawyer and client was so great as to
result in a total lack of communication, precluding an
adequate defense. United States v. Best, 

, 947
(7th Cir. 2005); United States v. Harris, 

, 552
(7th Cir. 2005). Additionally, even if the district court
4                                              No. 06-4373

abused its discretion, Ryals is not entitled to a new
sentencing hearing unless he shows that the error caused
him prejudice, meaning that but for the error, there is
a reasonable probability that the sentencing would have
produced a different result. 

;
see generally Strickland v. Washington, 

,
694 (1984).
   The government contends that counsel’s motion to
withdraw, which was filed three weeks prior to the
sentencing hearing, was untimely. We found a motion for
new counsel filed ten days before a sentencing hear-
ing untimely in United States v. Hall, 

, 313-14
(7th Cir. 1994), and punted on the timeliness of a motion
filed three weeks before sentencing in a case involving
a guilty plea in United States v. Bjorkman, 

, 500-01 (7th Cir. 2001). Here, the government won’t
even grant Ryals those three weeks. It says that counsel’s
motion was terse and the reasons behind it did not
fully emerge until the hearing itself, so even if the motion
was filed three weeks before sentencing, it wasn’t really
filed until the hearing date. But it would be inappro-
priate to blame this on Ryals: he wanted a new lawyer
and told his lawyer to move to withdraw but the lawyer
didn’t file a very good motion, so Ryals should be penal-
ized? Moreover, even though the timeliness of a motion
filed three weeks before sentencing was a close question
in Bjorkman, here we conclude that counsel’s motion
was timely, for it appears that Ryals and his lawyer did
not have their falling out until they began preparing for
the sentencing hearing. The motion to withdraw could not
have preceded the breakdown. See 

(suggesting that motion is timely if made at time
of dispute with lawyer).
  On the second factor, Ryals contends that the district
court did not adequately inquire into the dispute between
lawyer and client, and we agree. See United States v.
No. 06-4373                                              5

Zillges, 

, 371 (7th Cir. 1992). The district
judge asked counsel all of two questions: whether he
was familiar with the case, and whether he could ade-
quately represent Ryals at the hearing. When counsel
unequivocally answered “no” to the second question, bells
and whistles should have gone off. The court should have
inquired further, asking why counsel could not carry on,
what had caused the dispute between lawyer and client,
and whether the breakdown in their relationship was
beyond fixing. See 

(court did
not merely seek to elicit statement of general satisfaction
with counsel or dismiss matter in conclusory fashion);
United States v. McKenna, 

, 843-44 (9th Cir.
2003) (court held lengthy in camera hearing, asking
“specific questions” and receiving “detailed answers”).
Moreover, unless there was a good reason for delay, the
court should have taken up the matter soon after the
filing of the motion, rather than waiting three weeks
until the day of the sentencing hearing—a course that
suggested that the motion’s denial was a foregone con-
clusion because there would have been insufficient time to
appoint a new lawyer for a hearing on the same day. In
this regard it is significant that Ryals was not, by all
indications, trying to delay his sentencing, e.g., United
States v. Mooneyham, 

, 292 (6th Cir. 2007), or
casually rejecting the latest in a series of appointments,
e.g., United States v. Mentzos, 

, 839 (8th Cir.
2006). This was his first indication of dissatisfaction
with any appointed lawyer, and it was based on a genuine
and unbridgeable disagreement about the course of the
representation. These points suggest that this was a
matter to be taken up quickly and seriously. But when
the district court turned to the motion it did not even
follow up on counsel’s answer; instead, it heard a para-
graph’s worth of transcript from Ryals, and then denied
the motion outright.
6                                             No. 06-4373

  This leads to the third factor, whether communication
between lawyer and client had completely broken down.
We believe that it had. Ryals and his attorney were not
simply disputing a tactic or two and otherwise collaborat-
ing on his defense, as in United States v. Huston, 

, 1168 (7th Cir. 2002)—they were standing apart
from each other with folded arms. The transcript re-
veals that Ryals essentially represented himself at the
sentencing hearing, with very little participation from
counsel. Indeed, when the court asked counsel for his
views on the appropriate sentence, counsel seemed sur-
prised and said, “I’m assuming that I’ve still not been
relieved.” Counsel’s scant participation in the sentenc-
ing is significant because in the “irretrievable break-
down” inquiry, courts consider whether, notwithstanding
any disagreement between lawyer and client, counsel
was still able to provide a vigorous defense. Id.; see also

; 

. But
here, counsel’s only substantive contribution at the
sentencing hearing was this:
     I think that the Court should be entertaining
     some period of time within the . . . 360-month
     range given the facts of this case, that is,
     should the Court go ahead and find that the
     guidelines are appropriate to impose. I don’t
     need to educate the Court on the law, God
     knows. However, the guideline ranges are
     advisory as this Court is well aware and
     I would be remiss if I didn’t remind the Court
     obviously that it does have some discretion
     should it see fit to go ahead and lower or
     impose—lower and impose sentence upon the
     defendant. I would note that Mr. Ryals was
     out for all of two months, as I reviewed the
     file, before he was reincarcerated on this
     instant charge, your Honor. I’ll leave that to
No. 06-4373                                              7

     the Court’s determination as it relates to the
     reasonableness of the sentence and impose
     the appropriate sentence.
As Ryals points out on appeal, this “argument” did more
harm than good by highlighting the fact that he offended
soon after being released from prison. That was the gov-
ernment’s first point in its own sentencing argument.
  We therefore conclude that the district court abused
its discretion by denying the motion for new counsel.
Ryals is entitled to a new sentencing hearing if this
error caused him prejudice, and we find that it did. A
more vigorous presentation at the end of the sentencing
hearing could well have swayed the district judge to
impose a sentence below the advisory Guidelines range of
360 months to life. While Ryals’s criminal history is not
negligible, he is also a young man who is being put away
for 30 years for a $50 part in a minor-league drug deal. He
indicated to his probation officer that he still has career
aspirations and wishes to go to college, and his PSR shows
that he has had problems with addiction to drugs and
alcohol. Counsel highlighted none of these points as
grounds for a below-Guidelines sentence, nor did he
refer to any of the factors set out at 18 U.S.C. § 3553(a).
We cannot know for certain that a better argument
would have swayed the district court, but we can be
certain that counsel’s argument stood almost no chance
of doing so.


                    III. CONCLUSION
  For these reasons, we VACATE the sentence and REMAND
for a new sentencing hearing. Circuit Rule 36 shall apply.
8                                        No. 06-4373

A true Copy:
      Teste:

                   ________________________________
                   Clerk of the United States Court of
                     Appeals for the Seventh Circuit




               USCA-02-C-0072—1-10-08