FOR PUBLICATION

UNITED STATES COURT OF APPEALS

FOR THE NINTH CIRCUIT

UNITED STATES OF AMERICA,  No. 10-10011

Plaintiff-Appellee, D.C. No.

v. 3:08-cr-00890-  MMC-2 JAY KENT,

Defendant-Appellant. ORDER AND

AMENDED

OPINION 

Appeal from the United States District Court

for the Northern District of California

Maxine M. Chesney, Senior District Judge, Presiding

Argued and Submitted

November 2, 2010—San Francisco, California

Filed February 8, 2011

Amended May 24, 2011

Before: Ronald M. Gould and Consuelo M. Callahan,

Circuit Judges, and Edward R. Korman,

Senior District Judge.*

Opinion by Judge Gould

*The Honorable Edward R. Korman, Senior United States District

Judge for the Eastern District of New York, sitting by designation. 

6815
COUNSEL

Barry J. Portman, Federal Public Defender, and Daniel P.

Blank (argued), Assistant Federal Public Defender, San Francisco, California, for defendant-appellant Jay Kent.

Joseph P. Russoniello, United States Attorney, and Amber S.

Rosen (argued), Assistant United States Attorney, San Jose,

California, for plaintiff-appellee United States of America.

ORDER

The opinion in the above-captioned matter filed on February 8, 2011, and published at 633 F.3d 920, is amended as follows:

6818 UNITED STATES v. KENT
At slip opinion page 2363, line 12, delete the first two sentences of this paragraph, from <The latter> through <462.>.

At slip opinion page 2364, line 14, insert a paragraph stating: <Accordingly, in the context of pretrial plea negotiations,

“vindictiveness will not be presumed simply from the fact that

a more severe charge followed on, or even resulted from, the

defendant’s exercise of a right.” Gamez-Orduno, 235 F.3d at

462. Kent argues that he is entitled to a presumption of vindictiveness on the ground that the prosecution’s decision to

file the § 851 information immediately followed, and was

causally related to, his choice to enter an unconditional guilty

plea. Gamez-Orduno directly forecloses that argument.> 

Move existing footnote 2 to after <at 462.> in aboveinserted text.

Within footnote 2, delete all text following <at 381))>.

Replace existing sentence beginning at slip opinion page

2364, line 14, with <We reject Kent’s argument that we

should apply a more lenient rule when enhanced charges do

not arise from the context of explicit plea negotiations.>

At slip opinion page 2364, lines 27-29, delete <Thus,

defendants challenging pretrial charging enhancements cannot

avail themselves of a presumption of vindictiveness.>

At slip opinion page 2365, lines 16-17, change <Although

the pretrial enhancement of charges cannot give rise to a presumption of prosecutorial vindictiveness> to <Although a presumption of vindictiveness is unavailable in this case>.

At slip opinion page 2365, line 20, change <id.> to <Goodwin, 457 U.S.>.

The panel has voted to deny the petition for panel rehearing. Judges Gould and Callahan have voted to deny the petiUNITED STATES v. KENT 6819
tion for rehearing en banc, and Judge Korman has so

recommended. The full court has been advised of the petition

for rehearing en banc and no judge has requested a vote on

whether to rehear the matter en banc. Fed. R. App. P. 35. The

petition for panel rehearing and the petition for rehearing en

banc are denied.

No future petitions for rehearing or rehearing en banc will

be entertained.

IT IS SO ORDERED.

OPINION

GOULD, Circuit Judge:

Jay Kent’s appeal of his conviction and sentence for drug

distribution offenses requires us to decide two questions:

First, once a defendant has stated before the district court his

or her intention to enter a guilty plea, is it an abuse of that

court’s discretion to accept a prosecutor’s filing of enhanced

charges against the defendant? Second, does a prosecutor act

with impermissible vindictiveness when he or she makes good

on a plea bargaining threat to enhance charges against a

defendant, despite the defendant’s willingness to plead guilty

unconditionally? Answering both questions in the negative,

we affirm Kent’s conviction and sentence.

I

Kent delivered 22.7 grams of crack cocaine to an FBI

source on July 16, 2008, in San Francisco. He was arrested

and charged by indictment for conspiring to possess with

intent to distribute five grams or more of crack cocaine and

possessing with intent to distribute five grams or more of

crack cocaine, in violation of 21 U.S.C. §§ 841(a)(1),

6820 UNITED STATES v. KENT
841(b)(1)(A)(iii), and 841(b)(1)(B)(iii). The Government did

not initially file an information pursuant to 21 U.S.C. § 851

alleging Kent’s prior felony convictions, which filing would

have very substantially raised the penalty range applicable to

Kent’s sentence, as it would be changed from between five

and forty years, absent the prior felonies, to between ten years

and life imprisonment.

After an initial exchange of discovery, Assistant United

States Attorney Drew Caputo told Kent’s attorney, Daniel

Blank, that the Government sought Kent’s cooperation as an

informant as part of a plea agreement, and that the Government would file the § 851 information if Kent pushed the case

toward trial. Blank asked if the Government would file the

§ 851 information if Kent agreed to plead guilty without

cooperating as an informant. Caputo answered, according to

Blank, that Caputo believed it would not.1

Several days later, Blank left a voicemail message for

Caputo conveying Kent’s intention to plead unconditionally

to the indictment, as well as Kent’s lack of interest in a cooperation agreement. Caputo then called back to tell Blank that

the Government intended to file the § 851 information unless

Kent agreed to cooperate, despite his willingness to plead

guilty. Caputo next mailed a letter to Blank, dated February

10, 2009, memorializing the Government’s position: 

[W]e intend to file an information alleging your client’s prior felony drug convictions unless Mr. Kent

agrees to plead guilty pursuant to a plea agreement

entered into with the United States. At present, the

only plea agreement that the United States is prepared to contemplate entering into with your client

is a cooperation agreement.

1Caputo disputes that he said this. However, the United States has said

that this disputed fact is immaterial, and that Kent’s account may be taken

as true in resolving this appeal. 

UNITED STATES v. KENT 6821
The United States characterizes this as an offer in the context

of plea negotiations, but Blank argues that formal negotiations

were never initiated, or, stated differently, that Blank never

began negotiating a plea agreement.

Further communications between counsel occurred when

they arrived for a status conference in the district court and

before the district judge on February 25, 2009. Upon their

arrival to court, Blank told Caputo that his client would, at

that hearing, seek to enter an unconditional guilty plea. The

advantage he sought to exploit in offering a surprise plea was

to prevent the Government from enhancing charges against

Kent by filing the § 851 information.

Blank began the proceeding by saying, “Good afternoon,

your Honor. Daniel Blank on behalf of Mr. Kent. Mr. Kent is

in custody. He is hoping to plead today.” Within moments,

Caputo unequivocally responded:

[T]he United States is going to file right now an

Information for increased punishment by reason of

prior felony drug conviction under 21 United States

Code Section 851. . . . I’m handing the original to

your [Honor’s] deputy clerk. I’m handing a service

copy to Mr. Blank . . ., and I would ask that the

Court arraign Mr. [Kent] on that 851 information in

the sense of notifying him of the increased punishment that’s specified in paragraph 5 of the information in advance of his entry of the open guilty plea.

In other words, Caputo sought to file, in court, a paper copy

of the § 851 information, which had not yet been filed electronically. Blank objected to the courtroom filing, and urged

that the district court take Kent’s plea before accepting the

information. Blank proposed that the court allow the parties

an opportunity to prepare briefs, after which the court would

decide whether to accept filing of the information before entry

of the plea. In a long colloquy with the attorneys, the court

6822 UNITED STATES v. KENT
stated its view that filing was a party’s unilateral act, accepted

the information as filed, and instructed Caputo to deliver the

document to the clerk’s office for electronic docketing. Blank

then opted to defer his client’s plea until the parties had

briefed whether the now-filed information should be struck.

The parties next appeared before the district court to present argument as to whether the § 851 information should be

struck for prosecutorial vindictiveness. Although it was not

disputed that the Government filed the § 851 information in

response to Kent’s stated intention to plead guilty unconditionally rather than pursuant to a cooperation agreement, the

district court denied Kent’s motion to strike the information.

Months later, Kent, with the Government’s consent, entered

conditional guilty pleas, reserving his right to appeal the

issues described above. At a subsequent hearing, the district

court sentenced Kent to ten years imprisonment, which is the

enhanced mandatory minimum sentence.

Kent timely appealed. We have jurisdiction pursuant to 28

U.S.C. § 1291 and 18 U.S.C. § 3742(a).

II

We first address whether the district court erred in accepting the courtroom filing of the § 851 information after Kent

had said he wanted to enter a guilty plea. “[J]udges exercise

substantial discretion over what happens inside the courtroom,” United States v. Simpson, 927 F.2d 1088, 1091 (9th

Cir. 1991), and when considering such decisions as accepting

the filing of a document, our review is for abuse of that discretion. See Muckleshoot Tribe v. Lummi Indian Tribe, 141

F.3d 1355, 1358 (9th Cir. 1998) (stating that litigation management decisions are reviewed for abuse of discretion); Hinton v. Pacific Enters., 5 F.3d 391, 395 (9th Cir. 1993)

(reviewing application of local rules for abuse of discretion).

[1] Federal and local rules govern the proper mode of filing. Federal Rule of Criminal Procedure 49 states that filing

UNITED STATES v. KENT 6823
must be made “in a manner provided for a civil action.” Fed.

R. Crim. P. 49(d). The corollary civil rule, Federal Rule of

Civil Procedure 5, provides, “A paper is filed by delivering it

. . . to a judge who agrees to accept it for filing, and who must

then note the filing date on the paper and promptly send it to

the clerk.” Fed. R. Civ. P. 5(d)(2). Further, “[a] court may, by

local rule, allow papers to be filed . . . by electronic means

. . . .” Fed. R. Civ. P. 5(d)(3). The Northern District of California’s applicable local rule provides, “In any case subject to

electronic filing, all documents required to be filed with the

Clerk shall be filed electronically on the ECF web site, except

as . . . authorized otherwise by the court.” N.D. Cal. Gen.

Ord. 45(VI)(A) (emphasis added). Here, the district court’s

decision to authorize the courtroom filing of an information

was entirely permissible under these controlling rules.

Kent relies upon Ninth Circuit precedents that bar district

courts from rejecting entered pleas. E.g., Garcia-Aguilar v.

U.S. Dist. Ct. for S. Dist. of Cal., 535 F.3d 1021, 1025 (9th

Cir. 2008); In re Vasquez-Ramirez, 443 F.3d 692, 695-96 (9th

Cir. 2006). But, as we see it, these precedents have no relevance to this appeal. First, the district court never rejected

Kent’s plea. Kent was free to plead at the hearing, but instead

opted to wait in light of the court’s acceptance of the § 851

information. Second, these precedents involve rejection of

pleas that have satisfied the requirements of Rule 11. See

Vasquez-Ramirez, 443 F.3d at 695-96 (“[I]t is clear that a

court must accept an unconditional guilty plea, so long as the

Rule 11(b) requirements are met.”). Here, the plea was not

entered and the requirements of Rule 11 had not been satisfied.

[2] A district court need not drop everything to conduct a

Rule 11 colloquy the moment a defendant offers to enter a

guilty plea. “All federal courts are vested with inherent powers enabling them to manage their cases and courtrooms

effectively . . . .” Aloe Vera of Am., Inc. v. United States, 376

F.3d 960, 964-65 (9th Cir. 2004) (per curiam) (quoting F.J.

6824 UNITED STATES v. KENT
Hanshaw Enters., Inc. v. Emerald River Dev., Inc., 244 F.3d

1128, 1136 (9th Cir. 2001)). The federal appellate courts

should hesitate to intrude upon the “broad inherent powers [of

district courts] to manage their own affairs so as to achieve

the orderly and expeditious disposition of cases.” Sherman v.

United States, 801 F.2d 1133, 1135 (9th Cir. 1986) (internal

citation and quotation marks omitted). We hold that the district court committed no error when, before taking Kent’s

plea, it first accepted the Government’s filing of an information.

III

[3] We next address whether a prosecutor who carries out

a plea bargaining threat to enhance charges against a defendant, despite the defendant’s willingness to plead guilty

unconditionally, acts with impermissible vindictiveness.

A

[4] For more than two decades, our vindictive prosecution

cases have said that the standard of review is unsettled in this

circuit. E.g., United States v. Gann, 732 F.2d 714, 724 (9th

Cir. 1984). In recent years, all of our vindictive prosecution

cases, after mentioning the uncertainty of our precedents,

have proceeded to apply de novo review. E.g., United States

v. Jenkins, 504 F.3d 694, 699 (9th Cir. 2007); United States

v. Lopez, 474 F.3d 1208, 1211 (9th Cir. 2007). Review for

abuse of discretion may have been appropriate when district

judges based determinations of vindictive prosecution, like

other findings of attorney misconduct, on their subjective perceptions of the litigation unfolding in their courtrooms. See,

e.g., United States v. Griffin, 617 F.2d 1342, 1348 (9th Cir.

1980) (“Consideration of the vindictive prosecution claim

necessitates, in some cases, an ad hoc determination of

whether the defendant has reason to perceive a vindictive

motive.”). Review for clear error may have been appropriate—and may still be appropriate—when a determination of

UNITED STATES v. KENT 6825
vindictive prosecution turned upon factual findings. See, e.g.,

United States v. DeMarco, 550 F.2d 1224, 1226 (9th Cir.

1977) (holding that factual findings necessary to determination of vindictive prosecution were “amply supported by the

record”). Since a robust doctrine of vindictive prosecution has

developed, however, our review is now more commonly for

mistakes of law, for which de novo review is appropriate. See

United States v. Barner, 441 F.3d 1310, 1315 (11th Cir.

2006). We therefore take this opportunity to clarify that where

our vindictive prosecution inquiry turns upon a district court’s

proper application of the law, our review is de novo.

B

[5] “A prosecutor violates due process when he seeks additional charges solely to punish a defendant for exercising a

constitutional or statutory right.” United States v. GamezOrduno, 235 F.3d 453, 462 (9th Cir. 2000) (citing Bordenkircher v. Hayes, 434 U.S. 357, 363 (1978)). A defendant may

establish vindictive prosecution (1) “by producing direct evidence of the prosecutor’s punitive motivation . . . ,” United

States v. Jenkins, 504 F.3d 694, 699 (9th Cir. 2007), or (2) by

showing that the circumstances establish a “reasonable likelihood of vindictiveness,” thus giving rise to a presumption that

the Government must in turn rebut, United States v. Goodwin,

457 U.S. 368, 373 (1982).

[6] For good reasons, the Supreme Court has urged deference to pretrial charging decisions. “In the course of preparing

a case for trial, the prosecutor may uncover additional information that suggests a basis for further prosecution or he simply may come to realize that information possessed by the

State has a broader significance. At [the pretrial] stage . . . ,

the prosecutor’s assessment of the proper extent of prosecution may not have crystalized.” Goodwin, 457 U.S. at 381.

Also, in the plea negotiation context, the prosecutor’s latitude

to threaten harsher charges to secure a plea agreement

advances the interest in avoiding trial shared by the prosecu6826 UNITED STATES v. KENT
tor, defendant, and public. Bordenkircher, 434 U.S. at 363-64.

Finally, prompting prosecutors to file the harshest possible

charges at the outset “would [cause] prejudic[e] to defendants,

for an accused ‘would bargain against a greater charge, face

the likelihood of increased bail, and run the risk that the court

would be less inclined to accept a bargained plea.’ ” Goodwin,

457 U.S. at 378 n.10 (quoting Bordenkircher, 434 U.S. at 368

(Blackmun, J., dissenting)). Allowing prosecutors the leeway

at first to withhold more severe charges also spares defendants damage to their reputation that could result from the piling on of charges. Id. For these reasons, the prosecutor’s

“initial [charging] decision should not freeze [his or her]

future conduct.” Goodwin, 457 U.S. at 382.

Accordingly, in the context of pretrial plea negotiations,

“vindictiveness will not be presumed simply from the fact that

a more severe charge followed on, or even resulted from, the

defendant’s exercise of a right.” Gamez-Orduno, 235 F.3d at

462.2 Kent argues that he is entitled to a presumption of vindictiveness on the ground that the prosecution’s decision to

file the § 851 information immediately followed, and was

causally related to, his choice to enter an unconditional guilty

plea. Gamez-Orduno directly forecloses that argument.

We reject Kent’s argument that we should apply a more

lenient rule when enhanced charges do not arise from the context of explicit plea negotiations. Our cases do not draw this

distinction, Austin, 902 F.2d at 745, and we are admonished

against expanding the class of cases to which the vindictiveness presumption applies, Wasman v. United States, 468 U.S.

559, 566-67 (1984). Although enhanced charges will often

accompany failed plea negotiations, prosecutors may add

charges pretrial for any number of permissible reasons, such

2

See also United States v. Austin, 902 F.2d 743, 745 (9th Cir. 1990)

(“That the prosecution adds charges pretrial after a defendant asserts some

right does not establish a presumption of vindictiveness.” (citing Goodwin,

457 U.S. at 381)). 

UNITED STATES v. KENT 6827
as coming to a new understanding of the crime or evidence.

Goodwin, 457 U.S. at 381. The Supreme Court has urged deference to a prosecutor’s discretion to elevate charges in light

of the pretrial “timing” of such conduct, not just its factual

context. Id.

[7] Kent’s argument fails for a second reason: The

enhanced charges in his case did arise in the plea negotiation

context. By letter to Kent’s attorney dated February 10, 2009,

the Government made a plea offer, threatening to file the

§ 851 information “unless Mr. Kent agrees to plead guilty

pursuant to . . . a cooperation agreement.” At the February

25th hearing, Kent effectively rejected this plea offer by stating his intention to enter an unconditional plea rather than

cooperate. In response, the United States carried out its plea

threat by filing the § 851 information. Kent offers no authority for the untenable proposition that a defense attorney who

does not respond to a written plea offer has unilaterally opted

out of negotiations. Our cases suggest just the opposite. See,

e.g., Gamez-Orduno, 235 F.3d at 463 (holding that a prosecutor’s letter threatening to seek a superceding indictment established “the context of plea negotiations”). But even if we

accept Kent’s premise that he stopped short of engaging in

plea negotiations, it does not alter the prosecutor’s broad discretion to make a charging decision. As a general matter,

prosecutors may charge and negotiate as they wish.

C

[8] Although a presumption of vindictiveness is unavailable in this case, a defendant may still establish vindictive

prosecution by adducing direct evidence that punitive motives

precipitated the harsher charges. See Goodwin, 457 U.S. at

384 (“[W]e of course do not foreclose the possibility that a

defendant in an appropriate case might prove objectively that

the prosecutor’s [pretrial] charging decision was motivated by

a desire to punish him . . . .”). As a matter of law, the filing

of additional charges to make good on a plea bargaining threat

6828 UNITED STATES v. KENT
—as occurred here—will not establish the requisite punitive

motive, however. “[I]n the ‘give-and-take’ of plea bargaining,

there is no such element of punishment or retaliation so long

as the accused is free to accept or reject the prosecution’s

offer.” Bordenkircher, 434 U.S. at 363.

Kent argues that a prosecutor may carry out a plea bargaining threat of enhanced charges only when a defendant has

refused to plead guilty, not when he or she has rejected other

Government conditions. Our precedent has rejected this position. In United States v. North, we stated, “The government

may, in the course of plea bargaining, offer to reduce charges

or threaten reindictment under more serious charges, and it

may make good on either promise. It may do the same in

seeking cooperation in related prosecutions.” 746 F.2d 627,

632 (9th Cir. 1984) (emphasis added) (citations omitted),

abrogated on other grounds by Jacobson v. United States,

503 U.S. 540, 547 n.1 (1992). We reaffirm this rule.

[9] We have sanctioned the conditioning of plea agreements on acceptance of terms apart from pleading guilty,

including waiving appeal, United States v. Navarro-Botello,

912 F.2d 318, 321 (9th Cir. 1990), disclosing evidence,

United States v. Acuna, 9 F.3d 1442, 1445 (9th Cir. 1993),

providing testimony, Morris v. Woodford, 273 F.3d 826, 836

(9th Cir. 2001), and cooperating as an informant against others, United States v. Gardner, 611 F.2d 770, 773 (9th Cir.

1980). If prosecutors may permissibly demand these conditions, it follows that they may make good on threats to

enhance charges if these conditions are not accepted. See

United States v. Stanley, 928 F.2d 575, 579 (2d Cir. 1991)

(“[S]o long as the defendant was free to accept or reject the

prosecutor’s offer, the prosecutor may carry out his threat.”

(citing Bordenkircher, 434 U.S. at 363-65)). We hold that a

prosecutor who, in the plea negotiation context, threatens

enhanced charges to induce a defendant’s cooperation as an

informant may carry out that threat if the defendant declines

UNITED STATES v. KENT 6829
to cooperate, regardless of the defendant’s willingness to

plead guilty unconditionally to the lesser charges.3

[10] “[U]nder our system of separation of powers, the

decision whether to prosecute, and the decision as to the

charge to be filed, rests in the discretion of the Attorney General or his delegates, the United States Attorneys.” United

States v. Edmonson, 792 F.2d 1492, 1497 (9th Cir. 1986). “A

prosecutor should remain free before trial to exercise the

broad discretion entrusted to him to determine the extent of

the societal interest in prosecution.” Goodwin, 457 U.S. at

382. “[D]ue process does not in any sense forbid enhanced

sentences or charges, but only enhancement motivated by

actual vindictiveness toward the defendant for having exercised guaranteed rights.” Wasman, 468 U.S. at 568. The

record here is devoid of evidence that the Government, in filing the § 851 information, was motivated by vindictiveness

toward Kent.

AFFIRMED.

3We recently said in a related context in United States v. Morris: 

Unlike Bordenkircher, the government’s offer was conditioned

on Morris’s testifying in another trial. But we have repeatedly

held that deals conditioned on cooperation are permissible. See,

e.g., United States v. Gardner, 611 F.2d 770, 773 (9th Cir. 1980);

see also People of the Territory of Guam v. Fegurgur, 800 F.2d

1470, 1472 (9th Cir. 1986). The government premised the plea

bargain on Morris giving up many rights, including his statutory

right to seek release. Relinquishment of such rights is an acceptable part of most plea deals. 

No. 10-10009 (9th Cir. Feb. 2, 2011). 

6830 UNITED STATES v. KENT