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

No. 05-2655
UNITED STATES     OF   AMERICA,
                                                 Plaintiff-Appellee,
                                 v.

KARL BULLOCK,
                                            Defendant-Appellant.
                          ____________
            Appeal from the United States District Court
       for the Northern District of Illinois, Eastern Division.
         No. 03 CR 895—Samuel Der-Yeghiayan, Judge.
                          ____________
      ARGUED MAY 31, 2006—DECIDED JULY 18, 2006
                    ____________


 Before KANNE, EVANS, and SYKES, Circuit Judges.
   EVANS, Circuit Judge. After receiving what can best
be described as a whopper of a sentence—1,200 months in
a federal prison—Karl Bullock filed this appeal claiming
it was unreasonable. Today, we resolve his appeal.
  Bullock pleaded guilty to five counts of distributing
heroin. Each count carried a maximum penalty of 20 years.
21 U.S.C. § 841(b)(1)(C). The district court imposed the
maximum sentence for each of the counts, stringing them
together for a total sentence of 100 years. One hundred
years is a long time—one year longer, in fact, than the
standard lyrical shorthand for an unimaginably long
2                                                     No. 05-2655

sentence.1 Our task, under United States v. Booker, 

, 261 (2005), is to determine whether the sentence is
nevertheless reasonable.
  Bullock’s arrest came at the tail end of an investiga-
tion into drug sales by members of the Gangster Disciples
at the Rockwell Gardens housing project in Chicago,
particularly the building at 340 S. Western Avenue. As a
result of that investigation, more than two dozen people
were indicted in the case of United States v. Epps, 02 CR
895 (N.D. Ill.). Bullock would have been indicted along with
them, the government tells us, but he was arrested after
most of the other defendants had already pleaded guilty.
From the statements of some of those defendants, which are
included in Bullock’s presentence report, we learn that the
Rockwell Gardens operation got off the ground in July 1999
when Richard Epps, a Gangster Disciple “Overseer,” was
released from prison. Given responsibility by his gang
superiors for drug sales out of the 340 Building, Epps
organized a thriving crack-cocaine marketplace. His


1
   See, e.g., Bruce Springsteen, “Johnny 99” (“Well the evidence is
clear, gonna let the sentence, son, fit the crime / Prison for 98 and
a year and we’ll call it even, Johnny 99.”); Bob Dylan, “Percy’s
Song” (“It may be true he’s got a sentence to serve / But ninety-
nine years, he just don’t deserve.”); Johnny Cash, “Cocaine Blues”
(“The judge he smiled as he picked up his pen / Ninety-nine years
in the Folsom pen / Ninety-nine years underneath that ground / I
can’t forget the day I shot that bad bitch down.”); Ed Bruce,
“Ninety-Seven More To Go” (“Ninety-nine years go so slow / When
you still got ninety-seven more to go.”); Bill Anderson, “Ninety-
Nine” (“The picture’s still in front of my eyes, the echo in my ears
/ When the jury said he’s guilty and the judge said ninety-nine
years.”); Chloe Bain, “Ninety-Nine Years” (“The sentence was
sharp, folks, it cut like a knife / For ninety-nine years, folks, is
almost for life.”); Guy Mitchell, “Ninety-Nine Years” (“Ninety-nine
years in the penitentiary, baby, baby, wait for me, around twenty-
fifty-five we’ll get together dead or alive.”).
No. 05-2655                                                    3

workers typically dealt around half a kilogram of crack per
week, and sometimes that much in a single day.
   Bullock, too, was an Overseer in the Gangster Disciples,
but he wasn’t directly involved in this crack-dealing
scheme. His main territory was a couple of miles to the
west, in the neighborhood known as “K-Town” (where all
the street names begin with “K”2), and his primary product
line was heroin, not crack. But he knew a business opportu-
nity when he saw it, and he noticed that the demand for
heroin at Rockwell Gardens was going unmet. So in the
summer of 2000, Bullock obtained permission from Epps to
deal heroin out of the 340 Building, in exchange for a small
licencing fee of around $600 per week. Over the next 8
weeks, with the help of at least four fellow gang members,
Bullock sold somewhere around eight kilograms of heroin
from this new location.
  The material accompanying the presentence report is
primarily devoted to the extended details of this crack/
heroin conspiracy; only a small fraction of its nearly 200
pages touch on Bullock’s own involvement. The PSR also
briefly mentions a series of five transactions in the summer
of 2002 in which Bullock sold a total of 110 grams of heroin
to a government informant in his home base of K-Town.
These, then, were the six counts on which Bullock was
indicted: one count of conspiring to distribute crack and
heroin, and five counts of distributing heroin.
  As we said, Bullock pleaded guilty to the five heroin-
distribution counts. Although there was no formal plea
agreement, the government agreed that it would move at
sentencing to dismiss the conspiracy count. The government
reserved the right to argue, however, that the entire


2
  Specifically, the eight avenues between Pulaski and Cicero just
north of the Eisenhower expressway: Karlov, Keeler, Kildare,
Kostner, Kilbourn, Kolmar, Kenton, and Kilpatrick.
4                                                No. 05-2655

340 Building conspiracy was relevant conduct for pur-
poses of calculating Bullock’s advisory sentencing guideline
range. See U.S.S.G. § 1B1.3(a)(2). Although Bullock denied
that the conspiracy was relevant conduct, the presentence
report agreed with the government that the heroin sold in
the course of the conspiracy should be included in the
guideline analysis. But the PSR also concluded that there
was no evidence that Bullock was directly involved in the
sale of crack and so omitted those drug quantities from its
calculation.
  Despite the PSR’s recommendation, the district court
adopted the government’s view that the entire conspiracy
was relevant conduct and so held Bullock responsible not
only for the 110 grams of heroin which he admitted hav-
ing sold, but also the approximately 8 kilograms of heroin
and the more than 1.5 kilograms of crack sold from the 340
Building during the 8 weeks of Bullock’s involvement there.
This made an enormous difference in the guideline calcula-
tion: 110 grams of heroin corresponds to a base offense level
of 26; add 8 kilograms of heroin and you’re at level 34;
include more than 1.5 kilograms of crack and you get to
level 38. See § 2D1.1(c). The court added another 2 points
based on evidence that Bullock routinely carried a gun
while dealing, § 2D1.1(b), and another 3 points for his being
a manager or supervisor in criminal activity involving five
or more participants, § 3B1.1(b). The court considered
granting a 2-point reduction for acceptance of responsibility,
§ 3E1.1(1), but decided not to when Bullock refused to
acknowledge his involvement in the 340 Building conspir-
acy.
  That left the offense level at 43. The court calculated
a criminal history category of IV, but at level 43 the
criminal history category doesn’t matter—the guidelines
recommend life across the board. Recognizing the severity
of that sentence, the government suggested the court
exercise its post-Booker discretion to impose a lower
No. 05-2655                                                  5

sentence, something on the order of 30 years. But the
district judge was not feeling lenient. Stating that he had
considered the various sentencing factors given at 18 U.S.C.
§ 3553(a), he summarized his position: “After considering
all the evidence in this case, drug distribution tears into the
very fabric of society and results in the death of individuals
and destruction of families; and you, Mr. Bullock, have
significantly contributed to that.” The 1,200-month sentence
followed this observation.
  Bullock argues that his 100-year sentence is unreason-
able. (He also argues that it violates the Eighth Amend-
ment, but we always avoid addressing a constitutional
question if we can. See Rehman v. Gonzales, 

,
508-09 (7th Cir. 2006).) We have said that a sentence within
the properly calculated guideline range is presumptively
reasonable but that because the guidelines are now
trumped by the factors listed in § 3553(a), a defendant
can overcome the presumption by showing that his sentence
is unreasonable when measured against those factors. See
United States v. Mykytiuk, 

, 608 (7th Cir.
2005). Bullock makes passing reference to many of those
factors but relies primarily on § 3553(a)(6), which directs
the court to consider “the need to avoid unwarranted
sentence disparities among defendants with similar records
who have been found guilty of similar conduct.” He points
out that among the defendants who pleaded guilty in the
related case of United States v. Epps, none received a
sentence longer than 20 years, and of the three who went to
trial and lost, one was given 300 months and one got
480 months.3 In comparison, Bullock argues, his sentence
of 1200 months is clearly unreasonable.
  The government rightly observes that comparison with
codefendants is not usually enough to establish a sentenc-


3
    One, however, did receive a life sentence.
6                                                No. 05-2655

ing disparity for purposes of § 3553(a)(6). As we said in
United States v. Boscarino, 

, 638 (7th Cir.
2006), “the kind of ‘disparity’ with which § 3553(a)(6) is
concerned is an unjustified difference across judges (or
districts) rather than among defendants to a single case.”
To some extent, however, this proves Bullock’s point: the
defendants in Epps were party to a different case and were
sentenced by a different judge, leaving open the possibility
that Bullock’s sentence was unduly affected by the vagaries
of judicial assignment. And although Bullock hasn’t explic-
itly compared his sentence with those received by compara-
bly situated defendants nationwide, see United States v.
Newsom, 

, 689 (7th Cir. 2005), our own experi-
ence confirms that in the federal courts, where defendants
actually spend some 86 percent of their time behind bars, a
sentence of 100 years is quite unusual.
  Our doubts about the reasonableness of Bullock’s sen-
tence are reinforced when we consider how the court arrived
at his sentencing range: by including as relevant conduct
both the heroin and the cocaine sold out of the 340 Building
in the summer of 2000. In order to qualify as relevant
conduct, drug sales other than the offense of conviction
must be found to be “part of the same course of conduct or
common scheme or plan as the offense of conviction.” See
§ 1B1.3(a)(2); United States v. Johnson, 

, 878-
79 (7th Cir. 2003). Although § 1B1.3 cmt. n.9 provides broad
definitions of “same course of conduct” and “common scheme
or plan,” we have emphasized that in order to fall within
either definition, it is not enough that both offenses involve
the sale of drugs. See United States v. Crockett, 

,
730 (7th Cir. 1996) (“The mere fact that the defendant has
engaged in other drug transactions is not sufficient to
justify treating those transactions as ‘relevant conduct’ for
sentencing purposes.”); United States v. Duarte, 

, (vacating sentence based on aggregating uncharged
drug quantities where “[t]here is little, if anything, to
No. 05-2655                                                  7

suggest a temporal, geographical or any other relationship”
with the offense of conviction).
  In this case, Bullock pleaded guilty to five counts of
selling heroin. Those sales took place in K-Town in the
summer of 2002, two miles away from the 340 Building and
two years after Bullock’s alleged involvement with
the conspiracy there. Although the PSR treats Bullock’s
earlier heroin sales as part of the same course of conduct or
common scheme or plan as the later controlled purchases,
the connection is not self-evident. We have been wary of
treating as relevant conduct drug sales that took place that
far back in time. See United States v. Palmer, 

,
571 (7th Cir. 2001) (per curiam) (vacating sentence based in
part on uncharged drug sales that were “remote in
time—over 2 years old—to the sales . . . that form the basis
for the counts of conviction”); United States v. Ruiz,

, 882 (7th Cir. 1999) (“Where the gap in time
[between drug transactions] is as long as the two years in
this case, ‘we must be cautious and exacting in permitting
such relatively stale dealings to be included in the same
course of conduct as the offense of conviction.’ ”) (quoting
United States v. Cedano-Rojas, 

, 1180
(7th Cir. 1993)); 

. (“While lapse of
time between the two offenses is not in itself dispositive of
the question of relevance, it does suggest the separate
character of the two episodes.”) (citation omitted). It may
yet be possible to justify treating the earlier heroin sales as
relevant conduct chargeable to Bullock, but the reason
needs to be set out explicitly, not simply assumed. See
United States v. Sumner, 

, 539-40 (7th Cir.
2001) (“[W]hen a court relies entirely on the PSR to make
its relevant conduct finding, the PSR must explain how
the purported relevant conduct is part of the same course of
conduct or common scheme or plan as the offense of convic-
tion.”); 

(“To ensure that only
relevant conduct is included in calculating the sentence, the
8                                               No. 05-2655

government must carefully present the justification for the
inclusion of any uncharged acts and the court must, in turn,
set out its reasoning as clearly as possible.”).
  As for the crack component of the 340 Building conspir-
acy, it appears even more tenuously related to Bullock’s
offense of conviction. As justification for treating the
crack sales as relevant conduct, the government offered and
the court accepted the theory that Bullock’s heroin sales out
of the 340 Building benefitted from the security and other
organizational infrastructure that was already in place
there, thanks to the efforts of Richard Epps and his col-
leagues. But at most, this makes Epps’s crack trade rele-
vant conduct with respect to Bullock’s heroin sales from the
340 Building. It doesn’t make it relevant to Bullock’s actual
offense of conviction—selling heroin five times in K-Town in
2002. That is, it’s relevant only by association with other
relevant conduct, through a kind of criminal transitivity.
That’s not good enough—the connection to the offense of
conviction has to be direct. See United States v. Pinnock,

, 439 (D.C. Cir. 1995) (“[T]he government must
demonstrate a connection between count three [offered as
relevant conduct] and the offense of conviction, not between
count three and the other offenses offered as relevant
conduct.”) (emphasis in original). We doubt that any such
connection can be shown with respect to the more than
1.5 kilograms of crack the court used in calculating Bull-
ock’s guideline range.
  At the most, Bullock is responsible for somewhere in the
vicinity of 8 kilograms of heroin (and we emphasize, it
remains for the district court to support such a finding on
the basis of the record), which would give him a base
offense level of 34 and a maximum enhanced offense level
of 39. With a criminal history category of IV, his recom-
mended sentencing range would then be 360 months to life.
We also note that Bullock was denied acceptance-of-respon-
sibility points because he refused to admit involvement with
No. 05-2655                                                 9

Epps’s conspiracy. But if that conspiracy is not in fact
relevant conduct, Bullock’s refusal to admit involvement in
it cannot be considered falsely denying or frivolously
contesting relevant conduct. See U.S.S.G. § 3E1.1 cmt.
n.1(a). He would therefore be entitled to at least a 2-point
reduction, bringing his recommended range down to 292 to
365 months.
  These questions concerning relevant conduct need to be
resolved in the district court, and the court must then
decide how to exercise its discretion under Booker relative
to a properly calculated guideline range. As we said
in United States v. Robinson, 

, 701 (7th Cir.
2006), “[w]hen a judge does not properly calculate a guide-
lines sentence, our review for reasonableness is forestalled.”
For these reasons, we VACATE Bullock’s sentence and
REMAND for resentencing. Because we also conclude that it
would be best to have a new judge take a fresh look at the
case, Circuit Rule 36 shall apply on remand.
10                                        No. 05-2655

A true Copy:
      Teste:

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




               USCA-02-C-0072—7-18-06