United States v. Kent

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-
JAY KENT, MMC-2
Defendant-Appellant.
 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

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.

2353
2356 UNITED STATES v. KENT

COUNSEL

Barry J. Portman, Federal Public Defender, and Daniel P.
Blank (argued), Assistant Federal Public Defender, San Fran-
cisco, 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.
 UNITED STATES v. KENT 2357
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),
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 Govern-
ment would file the § 851 information if Kent pushed the case
toward trial. Blank asked if the Government would file the
2358 UNITED STATES v. KENT
§ 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 coop-
eration 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 cli-
ent’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 pre-
pared to contemplate entering into with your client
is a cooperation agreement.

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.
1
Caputo 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 2359
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 punish-
ment that’s specified in paragraph 5 of the informa-
tion 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 elec-
tronically. 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
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 pre-
sent 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 uncondi-
tionally 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
2360 UNITED STATES v. KENT
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 accept-
ing 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 court-
room,” 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 dis-
cretion. See Muckleshoot Tribe v. Lummi Indian Tribe, 141
F.3d 1355, 1358 (9th Cir. 1998) (stating that litigation man-
agement decisions are reviewed for abuse of discretion); Hin-
ton 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 fil-
ing. Federal Rule of Criminal Procedure 49 states that filing
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 Cali-
fornia’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
 UNITED STATES v. KENT 2361
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 rele-
vance 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 satis-
fied.

[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 pow-
ers 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.
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 dis-
trict court committed no error when, before taking Kent’s
plea, it first accepted the Government’s filing of an informa-
tion.

III

[3] We next address whether a prosecutor who carries out
a plea bargaining threat to enhance charges against a defen-
2362 UNITED STATES v. KENT
dant, 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 per-
ceptions 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 appropri-
ate—and may still be appropriate—when a determination of
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 determina-
tion 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 addi-
tional charges solely to punish a defendant for exercising a
 UNITED STATES v. KENT 2363
constitutional or statutory right.” United States v. Gamez-
Orduno, 235 F.3d 453, 462 (9th Cir. 2000) (citing Bordenkir-
cher v. Hayes, 434 U.S. 357, 363 (1978)). A defendant may
establish vindictive prosecution (1) “by producing direct evi-
dence 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 likeli-
hood 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] The latter route is unavailable where a prosecutor
enhances charges pretrial. Id. at 381-84. “[W]hen the addi-
tional charges are added during pretrial proceedings . . . vin-
dictiveness 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 For good reasons, the Supreme Court has urged defer-
ence to pretrial charging decisions. “In the course of preparing
a case for trial, the prosecutor may uncover additional infor-
mation that suggests a basis for further prosecution or he sim-
ply 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 prosecu-
tion 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 prosecu-
tor, defendant, and public. Bordenkircher, 434 U.S. at 363-64.
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)); 4 Wayne R. LaFave, Jerold H. Israel, Nancy J. King &
Orin S. Kerr, Criminal Procedure § 13.5(a) (3d ed. 2010) (stating that the
presumption of vindictiveness does not apply “in a pretrial setting because
a realistic likelihood of vindictiveness was deemed not to exist at that
stage”); id. at § 13.7(c) n.43 (citing First, Sixth, Seventh, Eighth, and
Ninth Circuit cases for this proposition).
2364 UNITED STATES v. KENT
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 defen-
dants damage to their reputation that could result from the pil-
ing 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.

We reject Kent’s argument that pretrial charging decisions
merit deference only when enhanced charges arise from the
context of explicit plea negotiations. Our cases do not draw
this distinction, Austin, 902 F.2d at 745, and we are admon-
ished against expanding the class of cases to which the vindic-
tiveness 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 as coming to a new understanding of the crime or evi-
dence. 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. Thus, defendants challenging pretrial
charging enhancements cannot avail themselves of a pre-
sumption of vindictiveness.

[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 stat-
ing his intention to enter an unconditional plea rather than
 UNITED STATES v. KENT 2365
cooperate. In response, the United States carried out its plea
threat by filing the § 851 information. Kent offers no author-
ity 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 prosecu-
tor’s letter threatening to seek a superceding indictment estab-
lished “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 dis-
cretion to make a charging decision. As a general matter,
prosecutors may charge and negotiate as they wish.

C

[8] Although the pretrial enhancement of charges cannot
give rise to a presumption of prosecutorial vindictiveness, a
defendant may still establish vindictive prosecution by adduc-
ing direct evidence that punitive motives precipitated the har-
sher charges. See id. 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—as occurred here—will not estab-
lish the requisite punitive motive, however. “[I]n the ‘give-
and-take’ of plea bargaining, there is no such element of pun-
ishment 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 bargain-
ing 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 posi-
tion. 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
2366 UNITED STATES v. KENT
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 agree-
ments 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 oth-
ers, United States v. Gardner, 611 F.2d 770, 773 (9th Cir.
1980). If prosecutors may permissibly demand these condi-
tions, 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
to cooperate, regardless of the defendant’s willingness to
plead guilty unconditionally to the lesser charges.3
3
We 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 accept-
able part of most plea deals.
No. 10-10009 (9th Cir. Feb. 2, 2011).
 UNITED STATES v. KENT 2367
[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 Gen-
eral 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 exer-
cised guaranteed rights.” Wasman, 468 U.S. at 568. The
record here is devoid of evidence that the Government, in fil-
ing the § 851 information, was motivated by vindictiveness
toward Kent.

AFFIRMED.