United States of America v. John Pauling, a/k/a JJ

In this case, a jury convicted defendant‐appellee John Pauling of

conspiring to distribute or possess with the intent to distribute 100 grams or

3

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.

6

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

14

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.

17

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

18

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 drugquantity

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).

19

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

20

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

22

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,

23

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

24

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).

25

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

26

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

27

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 fourmonth

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

28

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

29

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

AFFIRMED. The case is REMANDED for sentencing.