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Parties Involved:
Derrick Lavon Herring
Appellant
United States of America
Appellee

Document Text:

NOT RECOMMENDED FOR FULL-TEXT PUBLICATION

File Name: 16a0052n.06

Case No. 14-6398

UNITED STATES COURT OF APPEALS

FOR THE SIXTH CIRCUIT

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DERRICK LAVON HERRING,

Defendant-Appellant.

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ON APPEAL FROM THE UNITED 

STATES DISTRICT COURT FOR 

THE EASTERN DISTRICT OF 

KENTUCKY

BEFORE: DAUGHTREY, COOK, and WHITE, Circuit Judges.

COOK, Circuit Judge. A jury convicted Derrick Lavon Herring of conspiracy to 

distribute oxycodone in violation of 21 U.S.C. §§ 841(a)(1) and 846. The district court 

sentenced Herring to 168 months of imprisonment and four years of supervised release. Herring 

appeals both his conviction and sentence, and we affirm.

I.

Jody Gibson telephoned the police to report a theft of drugs and money. When the police 

arrived, Gibson admitted to trafficking drugs and to regularly purchasing oxycodone pills from a 

man he knew as “George”—an alias used by Herring. Believing that Herring orchestrated the 

robbery, Gibson agreed to participate in a controlled purchase to catch Herring.

On the day of the sting, with surveillance equipment in place, Gibson alerted the police

when the man he knew as “George” pulled into his driveway. Herring entered Gibson’s 

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residence as the police listened in on the transaction. When Gibson spoke the prearranged 

signal-words, the police swarmed the building and arrested Herring. A grand jury charged him 

with conspiracy to distribute oxycodone.

At trial, Gibson testified that his drug transactions with Herring began two to three

months before Herring’s arrest. Once or twice a week Herring would meet Gibson and sell him 

between 200 and 300 oxycodone pills. Gibson testified that he had seen Herring carrying as 

many as 800 pills at one time. Gibson personally used some of the pills and sold the rest. 

At times, Herring “fronted” Gibson pills, allowing Gibson to repay this debt as his own 

customers paid him. Herring also provided Gibson with a money counter to facilitate payments 

Gibson received from his own customers. On one occasion, Gibson held $30,000 for Herring.

Herring also gave Gibson two lockboxes to keep in his house for Herring to use in drug 

sales to customers other than Gibson. The pill-exchange scheme anticipated a dual key system:

the lockbox customer would have one key, and Herring would keep the other key to each box. 

One of Herring’s regular customers, Charles Oiler, testified that Herring offered him a key but 

that he refused. And though Herring told Gibson that an unnamed woman would have the key to 

the other lockbox, Kim Clemons—the only woman who testified—admitted to buying drugs 

from Herring but never addressed the lockbox scheme. Ultimately the lockboxes were never 

used. 

A jury convicted Herring of conspiracy to distribute oxycodone. The judge found 

Herring accountable for 8,000 30-milligram oxycodone pills, applied a leadership enhancement, 

and sentenced him to 168 months of imprisonment and four years of supervised release. 

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II.

Herring appeals, urging reversal of his conviction on two grounds: (1) the evidence was 

insufficient to establish a conspiracy, and (2) the prosecutor improperly appealed to the jurors’ 

community conscience.

1. Sufficiency of the Evidence to Sustain a Conviction for Conspiracy

Although the government devotes some of its briefing to the view that Herring failed to 

preserve his sufficiency objection by not renewing his Rule 29 motion at the close of all 

evidence, we decide under the de novo standard that the government presented evidence 

sufficient to convince a rational juror that Herring conspired with others to distribute oxycodone.

See United States v. Washington, 715 F.3d 975, 979 (6th Cir. 2013).

Herring argues that his dealings with Gibson, Oiler, and Clemons were a series of 

distinct, arms-length transactions, not a conspiracy to distribute. True, “a buyer-seller 

relationship is not alone sufficient to [establish] a conspiracy,” but one may exist “where there is 

additional evidence beyond the mere purchase or sale.” United States v. Anderson, 89 F.3d 

1306, 1310 (6th Cir. 1996) (citations and internal quotation marks omitted). Evidence of repeat 

purchases involving large quantities of drugs can support an inference of a conspiracy, see 

United States v. Martinez, 430 F.3d 317, 332–33 (6th Cir. 2005), and the trust involved in 

“fronting” drugs to a buyer can also demonstrate that a relationship is more than buyer-seller, see 

United States v. Lopez-Medina, 461 F.3d 724, 747 (6th Cir. 2006).

Herring’s argument fails to account for Gibson’s testimony concerning their arrangement. 

Indeed, at one point, Gibson held over $30,000 in cash for Herring and the pills were so plentiful 

that the two had trouble finding enough places to hide them at Gibson’s house. The “fronting” of

and delayed payments for drugs evidences Herring’s knowledge of and acquiescence in Gibson’s 

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reselling and thus cements this as a robust case of conspiracy. Oiler, too, testified that he resold 

Herring’s pills. And, of course, the lockbox scheme and the gifted money counter affirm 

Herring’s understanding and affirmation of the enterprise nature of his drug operation. A 

rational fact-finder presented with this evidence could readily infer each of the elements of a 

conspiracy to distribute. 

2. Improper Appeal to Jurors’ Community Conscience

Herring also contends that the prosecutor improperly appealed to the jurors’ community 

conscience when in closing argument he said:

Ladies and gentlemen, these little blue pills, oxycodone pills, are devastating our 

communities in southeastern Kentucky. We’re inundated with prescription pill 

abuse. You can watch it on the news, read it in the papers, and we see it in our 

streets and in our communities. And the defendant, Mr. Derrick Herring, is part 

of this problem. It’s impacting every aspect of our society. It impacts our 

economy, our healthcare system, and on an even more fundamental level, it 

impacts the relationships that we have with other people, including our families. 

It tears them apart. And you’ve had the opportunity to hear testimony from some 

people that have been impacted by this abuse and this addiction; Jody Gibson, 

Charles Oiler, Ms. Kim Clemons. And I don’t say these things to try to stir up 

sympathy for these people. The fact of the matter is that they’ve made a series of 

bad choices to engage in this lifestyle and to be part of this abuse and this 

addiction history and to use these substances, and they’ll have to answer for that 

in some way or form at some point in time.

But frankly, that’s not what we’re here to decide today. And that’s not the 

question before you. The sole issue that you have to decide is whether or not the 

defendant, Mr. Herring, or George, or whatever he wants to call himself, 

conspired with or agreed with these folks and others to distribute these pills and 

was part of this problem. And I would submit to you that the evidence establishes 

that he was, and he was part of this conspiracy.

* * * * *

[Y]ou can’t have street[-]level dealers, you can’t have these drug addicts without 

first having a source of supply. And that’s exactly what Mr. Herring was. 

Without people like him and others that are bringing these drugs in their area, you 

wouldn’t have people like Jody Gibson that was distributing them to individuals 

at street level. And it’s driven by greed and profit. And that’s why the plaintiff 

and law enforcement try to focus their efforts. A term we use sometimes is 

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cutting off the head of the snake. They try to go after the ring leaders or the 

higher people in these organizations, these sources of supply. . . . [S]ometimes 

[offering plea deals to lower-level dealers] is a necessary evil as a way to move up 

the food chain and get to these sources, and that’s exactly what they did here. 

They went after the source of supply.

Because Herring failed to object to these remarks at trial, we review for plain error. Fed. R.

Crim. P. 52(b). Prosecutorial misconduct may be so flagrant as to constitute plain error, but 

reversal is appropriate “only in exceptional circumstances in which the error is so plain that the 

trial judge . . . [was] derelict in countenancing it.” United States v. Henry, 545 F.3d 367, 376–77

(6th Cir. 2008) (quoting United States v. Emuegbunam, 268 F.3d 377, 406 (6th Cir. 2001)). 

To evaluate flagrancy, we consider “(1) whether the prosecutor’s remarks or conduct tended to 

mislead the jury or prejudice the accused; (2) whether the remarks were isolated or extensive; 

(3) whether the remarks were accidentally or deliberately made; and (4) the overall strength of 

the evidence against the accused.” United States v. Barnett, 398 F.3d 516, 522 (6th Cir. 2005).

While we afford prosecutors “wide latitude . . . during closing arguments,” United States 

v. Boyd, 640 F.3d 657, 669 (6th Cir. 2011), misconduct occurs when a prosecutor “direct[s] the 

jurors’ desires to end a social problem toward convicting a particular defendant.” United States 

v. Solivan, 937 F.2d 1146, 1153 (6th Cir. 1991). Prosecutors may not press the jury to “send a 

message to all [criminals] in the community by convicting the defendant,” United States v. 

Ghazaleh, 58 F.3d 240, 246 (6th Cir. 1995), because “[t]he amelioration of society’s woes is far 

too heavy a burden for the individual criminal defendant to bear.” Solivan, 937 F.2d at 1153

(quoting United States v. Monaghan, 741 F.2d 1434, 1441 (D.C. Cir. 1984)). 

The prosecutor’s argument in this case clearly was improper. His opening remarks 

focused upon Herring’s contribution to a regional drug problem, analogized Herring to a snake, 

and, contrary to the proscriptions set forth out in Solivan, explained how targeting and convicting 

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Herring and people engaged in similar activities would help address the area’s oxycodone 

problem. Although the prosecution argument did not promise that convicting Herring would 

eliminate the plague of oxycodone sales and addictions, the prosecutor did emphasize that there 

could be no drug dealers or drug addicts without supply sources, and that Herring was just such a 

supply source who should be targeted and removed from society.

Given the impropriety of the prosecutor’s argument, it is incumbent upon us to determine 

whether that misconduct was so flagrant as to constitute plain error. Our evaluation of the four 

flagrancy factors outlined in Barnett leads us to conclude that this is not the exceptional 

circumstance requiring a new trial. Even if the unfortunate remarks were prejudicial, misleading, 

and deliberately made, they were neither extensive nor repeated. Moreover, in light of the 

overwhelming evidence of Herring’s guilt, there is little chance that the comments influenced the 

verdict reached by the jury. Consequently, Herring is not entitled to a new trial based upon the 

prosecution’s closing argument.

III.

Herring also challenges his sentence on two grounds: (1) the drug-quantity determination 

was erroneous, and (2) the leadership enhancement was misapplied.

1. Erroneous Drug-Quantity Finding Resulting in a Procedurally Unreasonable Sentence

First, Herring claims that the district court erred in attributing 8,000 30-milligram 

oxycodone pills to him, thereby miscalculating his guidelines range and leading to a procedurally 

unreasonable sentence. We review for clear error a district court’s drug-quantity determination, 

with a key factor being the “extent to which the court identified the evidence upon which it relied 

in making [its] calculation.” United States v. Henley, 360 F.3d 509, 514–15 (6th Cir. 2004). 

Drug-quantity approximations are appropriate and not clearly erroneous if they are “supported by 

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competent evidence” and “err on the side of caution.” United States v. Hernandez, 227 F.3d 686, 

699 (6th Cir. 2000).

Here, the district court supported its approximation by reference to the following:

testimony that Herring gave Gibson approximately 500 pills once or twice a week for twelve to 

sixteen weeks; testimony that Herring held over 600 pills when arrested; the Presentence 

Investigation Report’s statement that Gibson told law enforcement that he once saw Herring with

over 2,000 pills; and Herring’s testimony that he possessed $30,000 for deposit at one time. 

From this evidence, the district court calculated the plausible pill-quantity range as between 

6,000 (500 pills per week over 12 weeks) and 16,000 (1,000 pills per week over 16 weeks). 

The district court settled on 8,000 pills, which was the presentencing report’s proposed figure, 

noting that it was consistent with the record and at the low end of the range.

The record shows that the district court based its reliance on the 500-pill figure on an 

incorrect statement by the government at sentencing. The government told the district court that

“what [Gibson] testified to at trial was that it was 500 pills once or twice a week.” But at trial, 

Gibson testified that Herring would deliver “200 to 300” pills “[p]robably twice a week,” 

although “sometimes [Herring] would leave more than that.” The 500-pill figure came from the 

trial testimony of Daryl Kegley, a detective in the Pulaski County Sheriff’s Office, and from the 

Presentence Investigation Report. According to Kegley, Gibson said that Herring would come 

“one or two times a week” and would “deliver around 500 pills usually.” In general, the district 

court’s calculations followed the Presentence Investigation Report, even when it deviated from 

the trial testimony. For example, the government represented that Gibson initially told law 

enforcement that Herring delivered pills over a “three- to four-month time frame,” but Gibson

testified at trial that he first met Herring “probably around September or October” or “[i]t could 

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have been August.” Given the arrest date in November, Gibson’s testimony supports a finding

of a two- to three-month range—at most, a reasonable upper bound would be three-and-a-half 

months—rather than the three- to four-month range in the Presentence Investigation Report.

However, the district court’s calculation of a base offense level of thirty is supported by

even a relatively conservative approximation derived from the evidence in the record. Oiler 

testified to purchasing 1,000 to 2,000 pills from Herring, Clemons testified to purchasing 

200 pills, and Herring had 648 pills when he was arrested. The most conservative estimate 

would attribute 1,848 pills to Gibson based on this evidence. In addition, Gibson testified that 

Herring delivered 200 to 300 pills “[p]robably twice a week” over the course of two to three 

months, and Kegley testified that Herring delivered the pills once or twice per week. Making a 

conservative estimate of 1.5 deliveries each week and 250 pills per delivery over ten weeks, the 

trial testimony supports that Herring gave or sold Gibson at least 3,750 pills over the course of 

their relationship. Combined, this conservative calculation supports a finding of 5,598 pills, 

which would still result in a base offense level of thirty.

1

Herring also faults the district court for relying on Gibson’s unreliable and unverifiable

testimony in determining the quantity of pills involved. Yet, testimony from a coconspirator 

“may be sufficient to determine the amount of drugs for which another coconspirator should be 

held accountable,” and we afford district courts “great deference” in credibility determinations

regarding such testimony. United States v. Jeross, 521 F.3d 562, 570 (6th Cir. 2008) (citation

 

1 Under the guidelines, the base offense level for a defendant convicted of oxycodone 

distribution is set by reference to the guideline range for an equivalent amount of marijuana. The 

district court calculated a base offense level of thirty for the equivalent of 1,000 to 3,000 

kilograms of marijuana. U.S.S.G. § 2D1.1(c)(5). One gram of oxycodone is equivalent to 6.7

kilograms of marijuana, id. § 2D1.1 cmt. n.8(D), so the relevant oxycodone range is 149 to 448 

grams. Here, a quantity of 5,598 thirty-milligram pills converts to 168 grams of oxycodone, 

which is enough to fall within the same thirty-level range calculated by the district court. 

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and internal quotation marks omitted). Though Gibson’s testimony wavered on specifics, he

consistently implicated Herring as regularly providing large quantities of pills to him for many 

weeks. Deferring, as we must, to the district court’s acceptance of Gibson’s testimony as the 

foundation for its calculation, it passes muster as not clearly erroneous.

Herring further argues that caution should have led the court to attribute fewer than 

8,000 pills to him. Although district courts should “err on the side of caution” when relying on 

circumstantial evidence to calculate drug quantities, Hernandez, 227 F.3d at 699, Herring points 

to no case requiring that a court select the lowest possible approximation. And we consistently 

uphold approximations supported by competent evidence. See e.g., Hernandez, 227 F.3d at 699;

United States v. Ward, 68 F.3d 146, 149–51 (6th Cir. 1995). Because the district court’s figure 

satisfies this standard, we find no clear error.

2. Misapplication of Leadership Enhancement

Next, Herring challenges the district court’s application of a two-level sentence 

enhancement for his leadership role in the conspiracy, pursuant to U.S.S.G. § 3B1.1. 

A defendant qualifies for this enhancement if “he has exercised decisionmaking authority, 

recruited accomplices, received a larger share of the profits, was instrumental in the planning 

phase of the criminal venture, or exercised control or authority over at least one accomplice.” 

United States v. Vasquez, 560 F.3d 461, 473 (6th Cir. 2009) (citing United States v. Lalonde, 

509 F.3d 750 765–66 (6th Cir. 2007)). Because this appeal is the first objection Herring has 

raised to the enhancement, we review for plain error. United States v. Vonner, 516 F.3d 382, 

385–86 (6th Cir. 2008).

Though Herring correctly maintains that no defendant earns a U.S.S.G. § 3B1.1

enhancement solely because he bought or sold drugs, see United States v. Schultz, 14 F.3d 1093, 

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1099 (6th Cir. 1994), Herring’s behavior goes beyond transacting drugs and demonstrates his 

exercise of authority over Gibson. Herring supplied Gibson with a money counter to track 

fronted drug proceeds; recruited him to deposit $30,000 into a checking account; and

spearheaded a lockbox scheme that, though unsuccessful, would have used Gibson to hold drugs

and cash for other dealers in the area. Accordingly, we find that the district court did not plainly 

err in applying the leadership enhancement at sentencing.

Discerning no reason to reverse the conviction or sentence, we AFFIRM.

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