United States of America v. John Pauling , A/ K / Ajj

17‐2539‐cr
United States v. Pauling
UNITED S TATES COURT OF APPEALS
F OR THE S ECOND CIRCUIT
August Term 2018
(Argued: October 23, 2018 Decided: May 23, 2019)
Docket No. 17‐2539‐cr
UNITED S TATES OF AMERICA,
Appellant,
v.
J OHN P AULING , A/ K / A JJ,
Defendant‐Appellee.
O N A PPEAL FROM THE U NITED S TATES D ISTRICT C OURT
FOR THE SOUTHERN D ISTRICT OF NEW Y ORK
Before:
K ATZMANN, Chief Judge, and KEARSE and C HIN, Circuit Judges.
Appeal by the government from an opinion and order of the United
States District Court for the Southern District of New York (Oetken, J.) granting
defendant‐appelleeʹs motion to vacate a portion of the juryʹs guilty verdict. After

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a four‐day trial, the jury convicted defendant‐appellee of conspiracy to distribute
100 grams or more of heroin as well as several other narcotics and firearms
violations. Defendant‐appellee moved to vacate the juryʹs verdict on the
conspiracy count, on the basis that the evidence at trial was insufficient to
establish the quantity element of the crime. The district court granted the
motion, vacated the juryʹs finding as to quantity, and entered a verdict of guilty
to a lesser included offense. The government appeals, arguing that it introduced
evidence sufficient to prove quantity and that therefore the juryʹs verdict should
be reinstated.
A FFIRMED and R EMANDED for sentencing.
JASON M. S WERGOLD, Assistant United States Attorney
(Amanda L. Houle, Micah W.J. Smith, Assistant
United States Attorneys, on the brief), for Geoffrey
S. Berman, United States Attorney for the
Southern District of New York, New York, New
York, for Appellant.
Y UANCHUNG L EE , Federal Defenders of New York, Inc.,
New York, New York, for Defendant‐Appellee.
___________
C HIN, Circuit Judge:
In this case, a jury convicted defendant‐appellee John Pauling of
conspiring to distribute or possess with the intent to distribute 100 grams or

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more of heroin. The parties agree that the government was required to prove
that the heroin in question was the subject of a conspiracy between Pauling and
one of his suppliers, referred to as ʺLowʺ (the ʺPauling‐Low conspiracyʺ), and
that the government proved beyond a reasonable doubt that 89 grams of heroin
were attributable to the Pauling‐Low conspiracy. The parties disagree, however,
as to whether the government proved that the Pauling‐Low conspiracy involved
the additional 11 grams of heroin necessary to reach the 100‐gram threshold.
The district court granted Paulingʹs motion pursuant to Federal Rule
of Criminal Procedure 29 to set aside his conviction on the conspiracy count on
the ground that the evidence introduced at trial failed to establish that an
additional 11 grams of heroin were attributable to the Pauling‐Low conspiracy.
Instead of entering judgment convicting Pauling of violating 21 U.S.C.
§§ 841(a)(1), 841(b)(1)(B) and 846, it entered judgment finding Pauling guilty of a
lesser included offense, a violation of 21 U.S.C. §§ 841(a)(1), 841(b)(1)(C), and 846.
The former offense carries a five‐year mandatory sentence for violations
involving 100 grams or more of heroin, while the latter offense carries no

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mandatory minimum and contains no quantity element.1 The government
appeals.
We conclude that the evidence at trial was insufficient to permit a
reasonable jury to find beyond a reasonable doubt that the Pauling‐Low
conspiracy involved an additional 11 grams of heroin. Accordingly, we affirm
and remand for sentencing.
BACKGROUND
A. Factual Background2
Between May 25 and July 14, 2016, the Drug Enforcement
Administration (ʺDEAʺ) intercepted phone calls between Pauling and various
associates, including an individual named ʺLow.ʺ On July 14, Pauling was
arrested by authorities. Upon his arrest, agents seized from Paulingʹs apartment
approximately 600 glassine bags, a digital scale, materials that could be used as a
1 See United States v. Facen, 812 F.3d 280, 283 n.1 (2d Cir. 2016) (noting that a
judgment of conviction under 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(C) is ʺin effect a
lesser‐included offenseʺ of 21 U.S.C. § 841(b)(1)(B) ʺwithout a mandatory minimum
sentenceʺ).
2 Our statement of facts views the evidence in the light most favorable to the
government, crediting any inference that the jury might have drawn in its favor. See
United States v. Rosemond, 841 F.3d 95, 99‐100 (2d Cir. 2016).

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cutting agent, and other paraphernalia associated with the distribution of
controlled substances.
Pauling concedes that the government established at trial that he
and Low conspired to distribute 89 grams of heroin. This was shown through
wiretap evidence of four transactions. On June 26, 2016, Pauling purchased 30
grams of heroin from Low for resale to a customer named ʺFlow.ʺ On June 27,
Pauling combined 10 grams of heroin he received from Low with 20 grams of a
cutting agent, for a total of 30 grams of heroin. On July 3, Pauling requested 14
grams of heroin from Low for a customer named ʺSteve.ʺ Finally, on July 11,
Low supplied Pauling with 11 grams of heroin, again for Steve, which Pauling
cut for a total of 15 grams. The four transactions thus involved a total of 89
grams of heroin.3
The conversation between Pauling and Steve about the July 3
transaction is at issue in this appeal. At 1:16 p.m. that day, Pauling spoke to
Steve about the quantity of heroin Steve wanted to order:
3 Pauling concedes that the quantity of the heroin in question is the weight with
the cutting agent included. See 21 U.S.C. § 841(b)(1)(B)(i) (providing penalties for the
distribution or possession with intent to distribute ʺ100 grams or more of a mixture or
substance containing a detectable amount of heroinʺ). The record indicates that at the
time of the conspiracy, a gram of heroin sold for approximately $65.

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PAULING: [T]ell me, the count, thatʹs, you know,
tomorrow.
STEVE: Iʹll meet you on, hold on one second. Iʹm on 17, as a
matter of fact, same thing as last time, same thing [as] last
time.
PAULING: Where was it? I forgot, shit because there was
so many people.
STEVE: Hold on, right, right. Iʹma go to, uh, 14th floor.
Appʹx at 122. The parties agree that the floor number was code for drug
quantity, in grams. Approximately three hours later, at 4:04 p.m., Pauling called
Low:
PAULING: Yo um, how we gonna do this cause my man
wants four‐fourteen right and he be down tomorrow and I
got some other people who want ‐‐
LOW: 14?
PAULING: Huh?
LOW: You said 14?
PAULING: Yeah, and I got these other people that want a
gram‐, two grams shit like that.
Id. at 124. There is no dispute that the July 3 calls account for 14 grams of heroin
attributable to the Pauling‐Low conspiracy, and this amount is included in the 89
grams discussed above. The parties disagree, however, about whether Steveʹs
reference to ʺsame thing as last timeʺ during the 1:16 p.m. call referred to a prior
14‐gram transaction of heroin supplied by Low. The government argues that it
did and that the total quantity of heroin attributable to the Pauling‐Low

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conspiracy was therefore 103 grams ‐‐ just over the 100‐gram threshold required
for the conspiracy count.
The wiretaps also provided information about the relationship
between Pauling and Low. Pauling owed Low money. Pauling was aware that
Low had a stash house for his narcotics, and he was aware that Lowʹs associate
ʺPlayʺ worked at the stash house. Pauling and Low discussed prices. On more
than one occasion, they discussed in detail the process of cutting narcotics and
the benefits of certain cutting agents.4 Pauling also indicated on several
occasions that he would help sell Lowʹs product.5 The government argues that
4 Appʹx at 114 (PAULING: ʺIʹm mixing this shit right now. . . . Iʹm squeezing it in
my hand . . . . I ainʹt gonna put it in no press. . . . I told you I put the strainer, right?
And then [unintelligible] I had to take a hammer and break it with a hammer, cut it
small and then I mashed it up . . . .ʺ); id. at 124‐25 (PAULING: ʺIʹma bring the machine
so we could press it all. . . . [Y]ou donʹt wanna smash it up? I mean you donʹt want to
press it? LOW: Yeah. Iʹve been wanted to do that all the week, nigga. Iʹve been calling
you man. . . . PAULING: Aight, so we can do it tomorrow then.ʺ); id. at 144‐45
(PAULING: ʺThey love it. Donʹt touch it. They love it. . . . [I]f we didnʹt have that
what we did last night, it would be too sticky . . . . And it was like all gooey. . . . [T]he
only thing that gets it like that is what we did last night. . . . Thatʹs what makes it better.
. . . And what I want to, right? Is . . . lie it out and, um, dry it out all the, the sweetness.
. . . [D]onʹt get no mix from nowhere else, just use that.ʺ).
5 Appʹx at 130 (PAULING: ʺIʹll help you get rid of that shit . . . this week.
[T]omorrow that shit will be gone.ʺ); id. at 116 (PAULING: ʺ[T]he queens thing is good.
. . . [I]tʹs already established.ʺ); id. at 124 (PAULING: ʺI got some other people who
want . . . a gram‐, two grams shit like that.ʺ); id. at 145‐46 (PAULING: ʺIʹm a move it off
for you. . . . Iʹm spend it with you anyway. . . . Iʹm a get rid of all that.ʺ); id. (LOW:
ʺ[W]e got a nice amount of that shit left, too. . . . PAULING: I got you, I, Iʹm a be hittinʹ
you . . . when, um, dude calls me.ʺ).

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this evidence proved circumstantially that Pauling and Low conspired to
distribute at least another 11 grams of heroin beyond the 89 grams discussed
above.
B. Procedural History
On July 14, 2016, the DEA arrested Pauling for his alleged
involvement with guns and drugs in the New York City area. The government
indicted Pauling on August 18, 2016, on five counts. The government filed a
superseding indictment on January 19, 2017, charging Pauling with eight counts:
(a) conspiring to distribute and to possess with intent to distribute 100 grams or
more of mixtures containing heroin, in violation of 21 U.S.C. §§ 841(a)(1),
841(b)(1)(B), and 846 (ʺCount Oneʺ); (b) three counts of distributing and
possessing with intent to distribute heroin, in violation of 21 U.S.C. §§ 812,
841(a)(1), and 841(b)(1)(C); (c) one count of firearms trafficking, in violation of 18
U.S.C. § 922(a)(1)(A) and (a)(2); (d) one count of using, carrying, or possessing a
firearm in connection with the heroin distribution conspiracy charged in Count
One, in violation of 18 U.S.C. § 924(c) (ʺCount Sixʺ); and (e) two counts of
possessing a firearm after sustaining a felony conviction, in violation of 18 U.S.C.
§ 922(g)(1).

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Trial began on February 13, 2017. At the close of the governmentʹs
case‐in‐chief on February 15, Pauling moved for a judgment of acquittal as to
Count One under Federal Rule of Criminal Procedure 29, citing insufficient
evidence to sustain a conviction. The court reserved decision. On February 16,
Pauling conceded in his closing argument that he was guilty of all counts except
for Counts One and Six. The jury returned its verdict later that day, finding
Pauling guilty of all but Count Six.
On March 24, 2017, Pauling renewed his motion under Rule 29 to
vacate and set aside the portion of the juryʹs verdict on Count One finding that at
least 100 grams of heroin were attributable to the Pauling‐Low conspiracy.
Pauling moved in the alternative for a new trial pursuant to Rule 33 as to that
count. He argued that the July 3 call could not support a jury finding of 28
grams by including the alleged prior 14‐gram transaction and that the 100‐gram
threshold was not otherwise proven beyond a reasonable doubt. The
government opposed both motions, arguing that the jury could have reasonably
inferred from the July 3 call that the ʺsame thing as last timeʺ referred to an
earlier transaction in which Pauling sold Steve 14 grams of heroin sourced from
Low. It argued that this prior 14‐gram transaction should be included, thus

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bringing the total quantity attributable to the Pauling‐Low conspiracy to 103
grams. It argued alternatively that the jury could reasonably infer from the
ʺclose working relationshipʺ between Pauling and Low that their conspiracy
extended ʺwell beyondʺ 100 grams. Appʹx at 216‐17.
On June 12, 2017, the district court granted Paulingʹs motion to
vacate and set aside his conviction on Count One and entered a verdict of guilty
to a lesser included offense. The district court also conditionally granted
Paulingʹs motion for a new trial, pending the outcome of this appeal. Paulingʹs
sentencing, scheduled for September 13, 2017, was stayed pending this appeal.
DISCUSSION
Pauling does not challenge the juryʹs finding that he participated in
a conspiracy with Low to distribute heroin. Nor does he dispute that the
evidence established that he directly participated with Low in the distribution of
89 grams of heroin. We are therefore presented with a single, discrete question:
Whether the government presented evidence sufficient for the jury to find
beyond a reasonable doubt that an additional 11 grams or more of heroin was
attributable to the Pauling‐Low conspiracy. The government argues that it did

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so, relying first on the July 3 telephone call and second on the evidence of an
ongoing relationship between Pauling and Low.
I. Applicable Law
The quantity of drugs involved in a violation of § 841(b)(1)(B) is an
element of the charged offense, see United States v. Gonzalez, 420 F.3d 111, 131 (2d
Cir. 2005), and the government has the burden of proving the charged quantity
beyond a reasonable doubt, id. at 120. The quantity element is met only if ʺa
single conspiracy,ʺ rather than ʺseparate agreements [that] may have been
charged under the umbrella of a single conspiracy count,ʺ crosses the quantity
threshold. United States v. Barnes, 158 F.3d 662, 670‐71 (2d Cir. 1998). Thus, while
the evidence at trial established that Pauling conspired to distribute over 200
grams of heroin with various individuals, see Appʹx at 202, it was the
governmentʹs burden with respect to Count One to prove that 100 or more of
those grams were attributable to a single conspiracy ‐‐ the Pauling‐Low
conspiracy.
Due process requires that essential elements of a crime be proven
beyond a reasonable doubt to ensure that ʺno person shall be made to suffer the
onus of a criminal conviction except upon sufficient proof.ʺ Jackson v. Virginia,

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443 U.S. 307, 316 (1979); see also In re Winship, 397 U.S. 358, 364 (1970). Rule 29 of
the Federal Rules of Criminal Procure is one means of protecting this
constitutional right; it enables the district court to vacate a conviction if it
concludes that ʺno rational trier of fact could find guilt beyond a reasonable
doubt.ʺ Jackson, 443 U.S. at 317; see also United States v. Coplan, 703 F.3d 46, 62 (2d
Cir. 2012) (ʺ[W]e will uphold the judgment[] of conviction if ʹany rational trier of
fact could have found the essential elements of the crime beyond a reasonable
doubt.ʹʺ (quoting Jackson, 443 U.S. at 319)). We review de novo a district courtʹs
grant of a Rule 29 motion based on a finding that the trial evidence was
insufficient to support the juryʹs verdict, applying the same standard the district
court applies in review of the evidence. United States v. Truman, 688 F.3d 129, 139
(2d Cir. 2012).
A defendant challenging a juryʹs guilty verdict ʺbears a heavy
burden.ʺ United States v. Martoma, 894 F.3d 64, 72 (2d Cir. 2017) (internal
quotation marks omitted). This is because, ʺ[i]n evaluating a sufficiency
challenge, we ʹmust view the evidence in the light most favorable to the
government, crediting every inference that could have been drawn in the
government’s favor, and deferring to the jury’s assessment of witness credibility

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and its assessment of the weight of the evidence.ʹʺ Id. (quoting Coplan, 703 F.3d
at 62). This deferential standard of review is ʺespecially important when
reviewing a conviction of conspiracy . . . because a conspiracy by its very nature
is a secretive operation, and it is a rare case where all aspects of a conspiracy can
be laid bare in court with the precision of a surgeonʹs scalpel.ʺ United States v.
Pitre, 960 F.2d 1112, 1121 (2d Cir. 1992) (internal quotation marks omitted).
ʺAn inference is not a suspicion or a guess. It is a reasoned, logical
decision to conclude that a disputed fact exists on the basis of another fact that is
known to exist.ʺ Siewe v. Gonzales, 480 F.3d 160, 168 (2d Cir. 2007) (alterations
omitted) (quoting Bickerstaff v. Vassar Coll., 196 F.3d 435, 448 (2d Cir. 1999)).
Impermissible speculation, on the other hand, is ʺa complete absence of
probative facts to support the conclusion reached.ʺ Lavendar v. Kurn, 327 U.S.
645, 653 (1946). While we must defer to a juryʹs reasonable inferences, we give
no deference to impermissible speculation. United States v. DʹAmato, 39 F.3d
1249, 1256 (2d Cir. 1994).
The line between permissible inference and impermissible
speculation ʺis drawn by the laws of logicʺ and not ʺjudicial idiosyncrasies.ʺ Tose
v. First Pa. Bank, N.A., 648 F.2d 879, 895 (3d Cir. 1981), abrogated on other grounds

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by Griggs v. Provident Consumer Discount Co., 459 U.S. 56 (1982). As the Supreme
Court has instructed, ʺthe essential requirement is that mere speculation be not
allowed to do duty for probative facts, after making due allowance for all
reasonably possible inferences favoring the party whose case is attacked.ʺ
Galloway v. United States, 319 U.S. 372, 395 (1943). Thus, in a criminal case, ʺthe
government must do more than introduce evidence ʹat least as consistent with
innocence as with guilt.ʹʺ DʹAmato, 39 F.3d at 1256 (quoting United States v.
Mulheren, 938 F.2d 364, 372 (2d Cir. 1991)).
At times it may be difficult to distinguish between inference and
speculation, as some speculation may indeed be reasonable. Reasonable
speculation occurs when the finder of fact concludes that a disputed fact exists
that is within the realm of possibility, but the conclusion reached is nevertheless
unreasonable because it is not logically based on another fact known to exist. See
Langston v. Smith, 630 F.3d 310, 314, 319 (2d Cir. 2011) (noting distinction between
ʺreasonable speculationʺ and ʺsufficient evidenceʺ); Leonard B. Sand et al.,
Modern Federal Jury Instructions § 6.01 (2011) (ʺThe process of drawing
inferences from facts in evidence is not a matter of guesswork or speculation. An
inference is a deduction or conclusion which . . . the jury [is] permitted to draw

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. . . from facts which have been established by either direct or circumstantial
evidence.ʺ); see also OʹLaughlin v. OʹBrien, 568 F.3d 287, 301‐02 (1st Cir. 2009);
Newman v. Metrish, 543 F.3d 793, 796‐97 (6th Cir. 2008). Indeed, we ʺmay not
credit inferences within the realm of possibility when those inferences are
unreasonable.ʺ United States v. Quattrone, 441 F.3d 153, 169 (2d Cir. 2006).
ʺ[W]here a fact to be proved is also an element of the offense ‐‐ here,
[drug quantity] ‐‐ it is not enough that the inferences in the governmentʹs favor
are permissible. We must also be satisfied that the inferences are sufficiently
supported to permit a rational juror to find that the element, like all elements, is
established beyond a reasonable doubt.ʺ United States v. Martinez, 54 F.3d 1040,
1043 (2d Cir. 1995); see also Sand et al., supra, § 6.01 (ʺ[W]hether based upon direct
or circumstantial evidence, or upon logical, reasonable inferences drawn from
such evidence, [the jury] must be satisfied of the guilt of the defendant beyond a
reasonable doubt before [it] may convict.ʺ). ʺ[I]t would not satisfy the
Constitution to have a jury determine that the defendant is probably guilty.ʺ
United States v. Lorenzo, 534 F.3d 153, 159 (2d Cir. 2008) (internal quotation marks
and alternations omitted).

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The drug quantity attributable to a defendant knowingly
participating in a drug distribution conspiracy includes (1) transactions in which
he participated directly, (2) transactions in which he did not personally
participate, but where he knew of the transactions or they were reasonably
foreseeable to him, and (3) quantities he agreed to distribute or possess with
intent to distribute ʺregardless of whether he ultimately committed the
substantive act.ʺ United States v. Jackson, 335 F.3d 170, 181 (2d Cir. 2003). 6
To prove the quantity by one of these means beyond a reasonable
doubt, the government must introduce specific evidence of drug quantities, or
evidence from which quantity can, through inference, be logically approximated
or extrapolated. See United States v. Archer, 671 F.3d 149, 163 (2d Cir. 2011)
(requiring ʺspecific evidenceʺ of quantity to sustain quantity‐based
enhancement). In the absence of such evidence, a juryʹs finding as to drug
quantity is nothing but ʺsurmise and conjecture.ʺ United States v. Shonubi, 998
F.2d 84, 90 (2d Cir. 1993). Compare United States v. Shonubi (ʺShonubi IIʺ), 103 F.3d
1085, 1092 (2d Cir. 1997) (approving of method of testing four randomly selected
heroin balloons to estimate quantity of heroin contained in 103 balloons found
6 The district court correctly charged the jury on this law. Trial Tr. at 573‐74.

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inside defendantʹs body), with id. (disapproving of extrapolation from quantity of
eighth trip that each of seven prior trips contained the same quantity). Thus,
while quantities of controlled substances in a drug distribution conspiracy
prosecution may be determined through extrapolation, approximation, or
deduction, there ordinarily must be evidence of known quantities, which are
sufficiently representative of the unknown quantities and from which an
approximation of the unknown quantities can logically be derived. See Archer,
671 F.3d at 163.
Two of our decisions, though summary orders, provide a framework
for understanding the role of representative proof in proving drug quantity. In
United States v. Adames, the defendant was convicted at trial of conspiracy to
distribute five or more kilograms of cocaine, and he challenged the sufficiency of
the evidence of quantity. 727 F. Appʹx 12 (2d Cir. 2018) (summary order). The
government introduced evidence linking the defendant to four seized packages.
Id. at 13. The seized packages contained one kilogram, 530 grams, two
kilograms, and 406 grams of cocaine, respectively, Governmentʹs Brief at 5‐9,
Adames, 727 F. Appʹx 12 (2d Cir. 2018) (No. 17‐1254) (describing packages 1, 4, 5,
and 9), for a total of 3.936 kilograms, Adames, 727 F. Appʹx at 13. Other evidence

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linked the defendant to five additional packages of unknown quantity, which the
government was unable to seize. Id. But one of these unseized packages
(package 6) was tracked online from an IP address associated with the
defendantʹs home and weighed approximately the same as a seized package
(package 5) that contained two kilograms of cocaine. Governmentʹs Brief, supra,
at 8‐9. Moreover, package 6 was briefly examined before delivery, and trial
testimony indicated that it contained ʺbrick shapedʺ objects. Id. In addition,
although the other unseized packages apparently were never weighed, ʺphone
records, witness testimony, and other circumstantial evidence establish[ed] that
these too were parcels of cocaine.ʺ Adames, 727 F. Appʹx at 13. In light of all the
circumstances, we held that ʺthe Government presented sufficient evidence for a
reasonable jury to infer the existence of an additional 1.06 kilograms from the
aggregate of the additional unseized packages.ʺ Id. at 14.
In United States v. Martinez, the defendant challenged a drug‐
quantity enhancement at sentencing. 133 F. Appʹx 762 (2d Cir. 2005) (summary
order).7 It was undisputed that the defendant was responsible for helping to
7 The proof necessary to satisfy an element of a charged crime beyond a reasonable
doubt is obviously more stringent than the proof required to establish that a sentencing
enhancement is warranted by the preponderance of the evidence. See generally United
States v. Booker, 543 U.S. 220 (2005).

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build nine vehicle ʺtrapsʺ in three cars used to hide packages of cocaine. Id. at
763‐64. The government seized cocaine in one of those traps, which contained 16
kilograms, and evidence showed that the defendant carried 19 kilograms from
another vehicle. Id. at 765. A trial witness testified that he saw the defendant
carrying another 20 kilograms of cocaine. Id. The district court concluded that
the defendant was responsible for over 150 kilograms ʺby averaging the three
known quantities attributable to [the defendant] ‐‐ 16, 19, and 20 kilograms ‐‐ and
multiplying by nine, the number of traps [defendant] built.ʺ Id. We vacated the
drug‐quantity enhancement, noting that ʺ[t]he average quantity of cocaine seized
or unloaded from the three cars is not ʹspecific evidenceʹ of the quantity of
cocaine actually transported in the nine traps built by [the defendant]ʺ because ʺit
is quite possible that the traps were used to transport some other contrabandʺ
and the evidence relied upon was not sufficiently reliable. Id.
Adames and Martinez illustrate how the total drug quantity
attributable to a defendant can (and cannot) be inferred or extrapolated from
known quantities. In Adames, it was reasonable to infer from evidence of four
seized packages, each containing a range of from 406 grams to two kilograms of
cocaine, that a total of at least an additional 1.06 kilograms of cocaine was

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contained in five unseized packages, one of which was known to have a similar
weight to a seized package containing two kilograms of cocaine. The seized
packages were sufficiently representative of the unseized packages to support
the inference that the unseized packages contained enough cocaine to reach the
quantity threshold. By contrast, in Martinez, it was not reasonable to infer from
evidence of two vehicle traps containing 16 and 19 kilograms of cocaine and
testimony that the defendant carried a package of approximately 20 kilograms of
cocaine that each of nine traps in three different cars contained the average of the
three known quantities. The seized packages were not sufficiently representative
of the unseized packages to support the inference that the seized and unseized
packages contained a similar quantity of cocaine. A similar lack of
representativeness arose in Shonubi II, in which we rejected the inference that
each of seven prior trips contained the same quantity of drugs as was seized in
the eighth trip. 103 F.3d at 1092.
II. Application
The government argues that it presented evidence sufficient for the
jury to find beyond a reasonable doubt that an additional 11 grams or more of
heroin was attributable to the Pauling‐Low conspiracy. It relies first on the July 3

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telephone call and second on the evidence of an ongoing relationship between
Pauling and Low. We discuss each in turn.
1. The July 3 Phone Call
The government argues that the evidence permitted the jury to infer
that an additional 14 grams of heroin was attributable to the Pauling‐Low
conspiracy by virtue of the July 3 phone call, in which the buyer mentioned that
he wanted the ʺsame thing as last timeʺ while placing an order for 14 grams of
heroin. Appʹx at 122. While we agree that the words ʺsame thing as last timeʺ
could have been a reference to a prior 14‐gram sale of heroin by Pauling to Steve,
we hold that no reasonable jury could have found beyond a reasonable doubt
that those 14 grams were sourced by Low. See Piaskowski v. Bett, 256 F.3d 687, 693
(7th Cir. 2001) (ʺAlthough a jury may infer facts from other facts that are
established by inference, each link in the chain of inferences must be sufficiently
strong to avoid a lapse into speculation.ʺ).
On the present record, the jury could not rationally conclude beyond
a reasonable doubt that a specific yet temporally unknown transaction, the
existence of which is evidenced solely by five words ‐‐ which were not uttered by
either Pauling or Low ‐‐ involved heroin provided by Low. The jury did not hear

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evidence as to who provided the heroin in this prior transaction, when the
transaction occurred, or what the circumstances were. To conclude so much on
the basis of so little amounts to impermissible speculation. Indeed, trial
testimony and wiretap evidence established that Pauling had other suppliers,
any one of whom could have supplied the heroin for that prior transaction. See
Trial Tr. at 175, 183; Appʹx at 83‐84, 88, 98, 100, 103, 127. And while the
government introduced evidence that Pauling distributed over 200 grams of
heroin, Appʹx at 202, it did not show that as much as half of that heroin was
supplied by Low. Accordingly, without something more, the jury could not
reasonably have concluded beyond a reasonable doubt that the words ʺsame
thing as last timeʺ referred to an additional 14 grams of heroin supplied by Low.
2. The Ongoing Relationship
The government argues that even if the July 3 phone call did not
prove that Pauling purchased an additional 14 grams of heroin from Low, it
would have been rational for the jury to conclude, based on the evidence of their
ongoing relationship, that Pauling and Low conspired to distribute at least an
additional 11 grams of heroin. Proof of drug quantity may be established
through proof of an agreement to distribute or possess with intent to distribute,

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regardless of whether the substantive act was actually completed. See Jackson,
335 F.3d at 181. The government asserts that there is ʺconcrete evidence of
Paulingʹs specific plans to continue to fill large orders through Low, which were
disrupted by Paulingʹs arrest,ʺ and that the jury could reasonably have inferred
that this agreement contemplated 11 or more grams of heroin. Governmentʹs Br.
at 35.
In support of this argument, the government points to the following.
First, Pauling and Low mixed and cut heroin together. Second, Pauling sold 89
grams of heroin sourced from Low. Third, Pauling and Low discussed a
customer from Queens, which Pauling described as ʺgoodʺ and ʺalready
established.ʺ Appʹx at 116. Fourth, Pauling knew that Lowʹs operation was large
enough to require one worker and a stash house. Finally, Pauling and Low had
specific discussions in which they appeared to contemplate future distribution of
drugs. For instance, on July 12, just before Pauling was arrested, Low told
Pauling that he had ʺa nice amount of that shit left,ʺ to which Pauling replied, ʺI
got you, I, Iʹm a be hittinʹ you . . . when, um, dude calls me.ʺ Id. at 146.
According to the government, it would be rational for a jury to infer, for

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example, that a ʺʹniceʹ amount was at least enough to fill one of Paulingʹs large
orders,ʺ that is, between 14 and 30 grams. Governmentʹs Br. at 35.
Over the course of the 17‐day period from June 26 to July 12, 2016,
Low supplied Pauling with 89 grams of heroin over four transactions ‐‐ an
average of 22.25 grams per transaction, with a low of 14 grams and a high of 30
grams. While it is certainly within the realm of possibility that the reference to ʺa
nice amountʺ meant 14 grams or 30 grams of heroin, it also could have referred
to a lesser quantity ‐‐ something more than the one‐ or two‐gram sales that
sometimes occurred but less than the 11 grams needed to reach the 100‐gram
threshold. See Quattrone, 441 F.3d at 169 (noting that ʺcourts may not credit
inferences within the realm of possibility when those inferences are
unreasonableʺ). On the present record, the conclusion that ʺa nice amountʺ
means 11 grams or more may be reasonable speculation, but it is still speculation
and therefore is an insufficient basis on which to rest a guilty verdict.8 See
8 In one transaction, Pauling tells a buyer, ʺI only got 10 grams here.ʺ Appʹx at 199.
It might be said that ʺonly . . . 10 gramsʺ contrasts with, rather than reflects, a ʺnice
amount,ʺ thus enabling the inference that a ʺnice amountʺ is something more than 10
grams of heroin. But considered in context, no such inference is possible. Pauling told
the purchaser that he ʺonlyʺ had 10 grams because he did not have enough heroin to fill
the buyerʹs 20‐gram order. See Trial Tr. at 123:21‐23 (ʺ[H]e didnʹt have enough. He
didnʹt have what I ordered. I ordered 20, and he didnʹt have enough grams of heroin to
give me. He only had ten . . . grams.ʺ).

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Langston, 630 F.3d at 314; see also OʹLaughlin, 568 F.3d at 302 (ʺThe instant facts
may support a reasonable speculation that OʹLaughlin was the assailant, but not
sufficient evidence to establish his guilt. Taken together, the circumstantial
evidence in this case, even when drawing all reasonable inferences in favor of the
prosecution, does not permit any rational jury to conclude that OʹLaughlin was
the assailant beyond a reasonable doubt.ʺ); Newman, 543 F.3d at 796‐97
(ʺAlthough circumstantial evidence alone can support a conviction, there are
times that it amounts to only a reasonable speculation and not to sufficient
evidence. . . . [W]here the evidence taken in the light most favorable to the
prosecution creates only a reasonable speculation that [an element of the crime is
met], there is insufficient evidence to satisfy the Jackson standard.ʺ). Because of
the lack of representative proof of the quantity represented by a ʺniceʺ amount,
the instant case is more like Martinez and Shonubi II than Adames.
And even assuming it was reasonable for the jury to infer that
Pauling and Low conspired to distribute an additional 11 or more grams of
heroin, ʺ[w]e must also be satisfied that the inferences are sufficiently supported
to permit a rational juror to find that the [quantity] element . . . is established
beyond a reasonable doubt.ʺ Martinez, 54 F.3d at 1043. In this case, we are not

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satisfied that the proof adduced by the government at trial could permit any
rational trier of fact to conclude, beyond a reasonable doubt, that Pauling and
Low conspired to distribute an additional 11 grams of heroin. See Jackson, 443
U.S. at 320 (ʺ[I]t could not seriously be argued that such a ʹmodicumʹ of evidence
could by itself rationally support a conviction beyond a reasonable doubt.ʺ).
Accordingly, the district court correctly determined that there was insufficient
evidence to support the juryʹs finding that Pauling and Low conspired to
distribute 100 grams or more of heroin and, thus, properly granted Paulingʹs
Rule 29 motion.
Our conclusion is supported by decisions of other courts. Many of
our sister circuits have reversed convictions where proof of drug quantity was
speculative on facts analogous to these. See United States v. Navarette‐Aguilar, 813
F.3d 785, 793, 796 (9th Cir. 2015) (rejecting governmentʹs argument that ʺpatternʺ
of drug dealing between conspirators ʺallowed the jury to infer a preexisting
agreement to distributeʺ 250 additional grams of heroin because ʺit would be
speculative to infer that the defendants agreed to any future transactions such
that they would reach the one kilogram markʺ); United States v. Daniels, 723 F.3d
562, 571 (5th Cir. 2013) (rejecting governmentʹs argument that distribution of five

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kilograms of cocaine was inferable from evidence of distribution of roughly 1.5
kilograms of cocaine to one buyer, combined with evidence of sales to six other
buyers, because, ʺwithout more evidence as to the quantity of these other sales,ʺ
finding of five kilograms was mere speculation); United States v. Hickman, 626
F.3d 756, 768‐70 (4th Cir. 2010) (rejecting governmentʹs argument that the four‐
month course of conduct between supplier and distributor was ʺpart of
something largerʺ such that jury could infer an additional 174 grams of heroin
because it would be based on a ʺhunch or intuition,ʺ and jury cannot ʺsimply
guess at the magnitude or frequency of unknown criminal activityʺ (internal
quotation marks omitted)).
To the extent the government separately argues that the substantial
interactions between Pauling and Low proved that additional quantities
distributed by Low were reasonably foreseeable to Pauling, we agree that such
an inference would be reasonable. But even so, based on the evidence here, no
jury could reasonably conclude that any specific quantity of heroin was
attributable to Low, beyond the undisputed 89 grams. The fact that Lowʹs
operation involved a stash house and a worker, and that Pauling was aware of
these facts, is simply not specific evidence of drug quantity. In the absence of

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any evidence indicating the quantities generally (or specifically) associated with
Lowʹs operation, quantity is not inferable. There is, therefore, no additional
quantity attributable to Low that Pauling could fairly be said to have reasonably
foreseen.
* * *
Although this is a close case that tests the boundary that exists
between the drawing of a permissible inference and impermissible speculation,
only surmise and guesswork could lead a jury to determine that Pauling and
Low conspired to distribute an additional 11 grams of heroin. ʺWe are obliged to
view the evidence with all reasonable inferences drawn in the Governmentʹs
favor, but we may not permit that rule to displace the even more important rule
that all elements of an offense must be proven beyond a reasonable doubt.ʺ
Martinez, 54 F.3d at 1049 (Newman, J., dissenting). While one could argue, based
on reasonable speculation, that it was ʺlikelyʺ or ʺprobableʺ that Low and Pauling
agreed to distribute an additional 11 grams of heroin, the government had to
prove more than likelihood or probability ‐‐ it had to prove an agreement to
distribute (or possess with intent to distribute) an additional 11 or more grams of
heroin beyond a reasonable doubt. See Lorenzo, 534 F.3d at 159 (noting that ʺit

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would not satisfy the Constitution to have a jury determine that the defendant is
probably guiltyʺ (internal quotation marks and alternations omitted)).
Because the government failed to do so, the district court correctly
determined, viewing all of the evidence in the light most favorable to the
government and crediting every inference in its favor, that the evidence at trial
was insufficient to support a jury finding that 100 or more grams of heroin were
attributable to the Pauling‐Low conspiracy.
CONCLUSION
For the reasons set forth above, the judgment of the district court is
A FFIRMED. The case is R EMANDED for sentencing.

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