FOR PUBLICATION
UNITED STATES COURT OF APPEALS
FOR THE NINTH CIRCUIT
UNITED STATES OF AMERICA, No. 10-50111
Plaintiff-Appellee, D.C. No.
v. 3:09-cr-03326-
MANUEL GONZALEZ-MELCHOR, LAB-1
Defendant-Appellant.
OPINION
Appeal from the United States District Court
for the Southern District of California
Larry A. Burns, District Judge, Presiding
Argued and Submitted
April 13, 2011—Pasadena, California
Filed July 8, 2011
Before: Dorothy W. Nelson, Senior Circuit Judge, and
Jay S. Bybee and Milan D. Smith, Jr., Circuit Judges.
Opinion by Judge Milan D. Smith, Jr.
9141
UNITED STATES v. GONZALEZ-MELCHOR 9143
COUNSEL
Kristi A. Hughes, Federal Public Defender, San Diego, Cali-
fornia, Attorney for the defendant-appellant.
Laura E. Duffy, United States Attorney, Bruce R. Castetter,
Assistant United States Attorney, and Rebecca S. Kanter,
Assistant United States Attorney, San Diego, California,
Attorneys for the plaintiff-appellee.
9144 UNITED STATES v. GONZALEZ-MELCHOR
OPINION
M. SMITH, Circuit Judge:
Defendant-Appellant Manuel Gonzalez-Melchor appeals
his conviction and sixty-three-month sentence for reentry
after deportation in violation of 8 U.S.C. § 1326. Gonzalez-
Melchor contends that his deportation was invalid because the
immigration judge (IJ) failed to advise him of his eligibility
for voluntary departure. The government claims that we need
not reach that question because Gonzalez-Melchor waived his
right to appeal.
We hold that the appellate waiver, negotiated by the district
court at sentencing in exchange for a reduced sentence, is
invalid and unenforceable. In a memorandum disposition filed
contemporaneously with this opinion, we hold that the IJ
failed adequately to advise Gonzalez-Melchor of his ability to
apply for voluntary departure, and we remand for the district
court to determine whether Gonzalez-Melchor was prejudiced
by that failure.
FACTUAL AND PROCEDURAL BACKGROUND
On June 27, 2009, United States Border Patrol agents,
responding to a seismic intrusion device near Otay Mesa, Cal-
ifornia approximately one mile north of the United States-
Mexico border, found Gonzalez-Melchor hiding in the brush.
Gonzalez-Melchor, a citizen of Mexico, admitted to being in
the United States without valid immigration documents. A
routine records check revealed that Gonzalez-Melchor had
previously been deported from the United States.
The relevant facts concerning the underlying deportation
hearing are as follows: On September 8, 1995, Gonzalez-
Melchor appeared before an IJ for a group deportation hear-
ing. At that hearing, Gonzalez-Melchor admitted that he pre-
UNITED STATES v. GONZALEZ-MELCHOR 9145
viously had crossed the border from Mexico six or seven
times without inspection.
The IJ explained his ruling to the group as follows:
[T]he only thing in the law that could possibly save
you from deportation is voluntary departure. But I’m
not considering you for that because I—I would not
give it to you even if you asked for it and I want you
to know the reasons. Voluntary departure is what the
law calls a privilege. This means you cannot have it
simply because you would like to [ ] get it. To
receive it you would have to show two things. First
that you qualify for it. Second, even if you do qual-
ify, that you have a good record which shows you
deserve the privilege.
Now I note that in some of your cases, you have
suffered within the past five years a conviction for a
drug offense or in the case of one man, for burglary,
and this criminal record disqualifies you from volun-
tary departure. For the rest of you, I see bad facts
which tells me you don’t deserve voluntary depar-
ture. For example, . . . [s]everal of you have entered
the country without inspection on previous occasions
. . . . I think the only fair and correct order for you
is deportation to Mexico.
The IJ then explained that each respondent had a right to
appeal the decision and asked each “to stand and tell me in a
loud and clear voice, either yes or no, whether you have any
interest at all in appeal.” Gonzalez-Melchor answered, “No.”
Four years later, on September 9, 2009, Gonzalez-Melchor
was indicted for one count of illegal reentry after deportation
in violation of 8 U.S.C. § 1326. He moved to dismiss the
indictment, arguing that the illegal reentry charge was based
on an invalid deportation because the IJ had failed to advise
9146 UNITED STATES v. GONZALEZ-MELCHOR
him of his ability to apply for voluntary departure, or to give
him the opportunity to develop a record to show his eligibility
for such relief.
The district court concluded that the IJ had failed to advise
Gonzalez-Melchor of his eligibility to apply for voluntary
departure because “in explaining the right, [the IJ] makes a
threshold announcement that he’s also made the decision.”
The court denied Gonzalez-Melchor’s motion to dismiss the
indictment, however, concluding that Gonzalez-Melchor had
validly waived his right to appeal to the district court, and had
not demonstrated prejudice because the IJ likely would not
have granted discretionary relief.
Gonzalez-Melchor waived his right to a jury trial and was
convicted of one count of illegal reentry after deportation. At
sentencing, the district court informed Gonzalez-Melchor that
he intended to reduce his sentence by two points for accep-
tance of responsibility, and noted, “[I]f I was convinced [you]
were going to stay out of the United States for good . . . then
that would persuade me that a sentence of less than whatever
we end up with once [you] get[ ] credit for responsibility
might be appropriate.” The following colloquy then ensued
between the district court, Gonzalez-Melchor, and his coun-
sel:
The Court: I’d also like to hear from
[Gonzalez-Melchor,] “look, I had
my day in court. My arguments
were heard. I don’t have a real
good argument . . . .”
And your experience is probably the
same as mine. [The Ninth Circuit is]
going to be reluctant to go the other
way on that. So he can take his appeal,
but it’s a long-shot. That—grounding
himself in some realism there con-
UNITED STATES v. GONZALEZ-MELCHOR 9147
vinces me of the bona fideness [sic] of
the promise that he’s going to stay out.
If I had that, then the sentence would
be quite different than what it might be
absent those things.
....
[A]n acknowledgment from him
that he’s not coming back any-
more, that he isn’t, that he prom-
ises me or looks me in the eye man
to man and says “I’m not coming
back anymore, and I’ll accept the
judgments of this court. I’m not
going to waste anybody else’s time
and money”—maybe I shouldn’t
say, “waste,” but “I’m not going to
expend additional resources to pur-
sue this thing. I’ll accept my fate,”
that would go a long way. He’d
probably be somewhere in the
range of 60, 65 months, something
like that, which is a substantial
reduction from where he is even
once he gets two points off [for
acceptance of responsibility].
Counsel: Can I just have a minute to speak
with Mr. Gonzalez?
The Court: Sure.
Counsel: Thank you.
(Pause in proceedings)
9148 UNITED STATES v. GONZALEZ-MELCHOR
Counsel: Thank you, your honor. He’s ready
to put this incident behind him and
he’ll waive appeal.
The Court: All right. Mr. Gonzalez, your law-
yer tells me that you’re prepared to
accept the judgment of this court
and waive any right to pursue any
appeals or challenges to rulings
that I’ve made; is that true?
Defendant: Yes, sir.
The Court: And [your counsel] has explained
to you the nature of your right in
that regard. You could pursue it
through the 9th Circuit and get a
judgment from the three judges on
a panel in the 9th Circuit and even
go further. But if you waive your
right to appeal, that would be an
end of your case today. Do you
understand?
Defendant: Yes, sir.
The Court: That’s what you want to do?
Defendant: Yes, sir.
The Court: Does he make that decision with
your concurrence?
Counsel: Yes, your honor.
The Court: You believe it’s voluntary on his
part?
UNITED STATES v. GONZALEZ-MELCHOR 9149
Counsel: I do, your honor.
The Court: The court finds that Mr. Gonzalez
has knowingly, voluntarily, and
intelligently waived his right to
appeal. I accept that waiver.
The district court sentenced Gonzalez-Melchor to sixty-three
months imprisonment, a “variance downward from the 84-
month bottom end of the guidelines.” Despite his putative
appellate waiver, Gonzalez-Melchor now appeals.
JURISDICTION AND STANDARD OF REVIEW
We have jurisdiction under 28 U.S.C. § 1291. We review
de novo whether an appellate waiver is valid. United States v.
Shimoda, 334 F.3d 846, 848 (9th Cir. 2003).
DISCUSSION
The government contends that we should dismiss the
appeal because Gonzalez-Melchor waived his appellate rights.
See 18 U.S.C. § 3742(a) (providing the statutory right for a
defendant to appeal his or her sentence). Gonzalez-Melchor
responds that the waiver is invalid and contends that Federal
Rule of Criminal Procedure 11(c)(1), which prohibits judicial
participation in plea negotiations, should also extend to
appellate-waiver negotiations at the sentencing phase. We
hold that the appellate waiver, negotiated by the district court
in this case, is invalid and unenforceable.
Generally, we retain jurisdiction over an appeal by a defen-
dant who has signed an appellate waiver, although “ ‘we will
not exercise that jurisdiction to review the merits of [a defen-
dant’s] appeal if we conclude that she knowingly and volun-
tarily waived her right to appeal.’ ” United States v. Jacobo
Castillo, 496 F.3d 947, 957 (9th Cir. 2007) (en banc) (quoting
United States v. Gwinnett, 483 F.3d 200, 203 (3d Cir. 2007)
9150 UNITED STATES v. GONZALEZ-MELCHOR
(alteration in original)). “A waiver is voluntary if, under the
totality of the circumstances, [it] was the product of a free and
deliberate choice rather than coercion or improper induce-
ment.” United States v. Doe, 155 F.3d 1070, 1074 (9th Cir.
1998) (en banc). However, “where a waiver is not the product
of the defendant’s free will—for example, where it has been
procured by government coercion or intimidation—the defen-
dant cannot be said to have knowingly and voluntarily relin-
quished his rights.” Jones v. United States, 167 F.3d 1142,
1145 (7th Cir. 1999). Accordingly, we must determine
whether the district court’s participation in negotiations ren-
dered Gonzalez-Melchor’s appellate waiver involuntary.
[1] Federal Rule of Criminal Procedure 11(c)(1) provides,
in relevant part: “An attorney for the government and the
defendant’s attorney, or the defendant when proceeding pro
se, may discuss and reach a plea agreement. The court must
not participate in these discussions.” Fed. R. Crim. P.
11(c)(1). The Federal Rules of Criminal Procedure thereby
expressly prohibit judicial participation in plea-agreement
negotiations, the setting in which appellate waivers typically
occur. See, e.g., Jacobo Castillo, 496 F.3d at 954 (“In general,
a defendant who enters into a plea agreement waives his right
to appeal his conviction.”); United States v. Portillo-Cano,
192 F.3d 1246, 1249 (9th Cir. 1999) (“Upon entering into an
enforceable [plea] agreement, [a defendant waives] his right
to appeal a sentence called for by the agreement.”) (citing 18
U.S.C. § 3742(c)). This is such a bright-line rule that “a find-
ing of judicial misconduct in connection with a plea proceed-
ing constitutes plain error and entitles a defendant to
withdraw his guilty plea even if the error is identified for the
first time on appeal.” United States v. Anderson, 993 F.2d
1435, 1437 (9th Cir. 1993).
[2] We construe a plea agreement as a contract between
the prosecutor and the defendant, United States v. Streich, 560
F.3d 926, 929-30 (9th Cir. 2009), with the district court acting
only as “a neutral arbiter of the criminal prosecution,” United
UNITED STATES v. GONZALEZ-MELCHOR 9151
States v. Bruce, 976 F.2d 552, 557 (9th Cir. 1992). Accord-
ingly, Rule 11(b)(1)(N) requires that, “[b]efore the court
accepts a plea of guilty . . . the court must address the defen-
dant personally in open court . . . [and] inform the defendant
of, and determine that the defendant understands . . . the terms
of any plea-agreement provision waiving the right to appeal
or collaterally attack the sentence.” Fed. R. Crim. P.
11(b)(1)(N). Where a district court improperly participates in
plea-agreement negotiations, however, the defendant’s “re-
sponses to the judge’s questioning during the formalistic col-
loquy do not allay our concerns regarding voluntariness.”
Anderson, 993 F.2d at 1438.
The risk of coercion is especially high where a district court
pressures a defendant for an immediate change of his or her
plea. In United States v. Anderson, we noted:
The judge’s opening pronouncement that he would
not after [the date of the hearing] accept a plea to
fewer than all thirty counts of the indictment and
admonishment that the government was not to
“make any deals,” aside from constituting improper
judicial intervention in the plea negotiation process,
. . . meant that Anderson had to decide immediately
whether he wished to change the not guilty plea he
had just entered to one of guilty . . . . [I]t is difficult
to imagine how Anderson could not have felt pres-
sured when confronted with the court’s “now or
never” tactics at the . . . hearing.
993 F.2d at 1437-38. Thus, the risk of coercion potentially is
even higher when a defendant must immediately respond to
the judge’s intervention in plea negotiations.
Rule 11(c)(1), at least arguably, does not expressly apply in
the context of this case because no plea-agreement discus-
sions took place. See, e.g., Bruce, 976 F.2d at 556 (stating that
the rule “simply commands that the judge not participate in,
9152 UNITED STATES v. GONZALEZ-MELCHOR
and remove him or herself from, any discussion of a plea
agreement that has not yet been agreed to by the parties in
open court”). We conclude, however, that a district court’s
direct negotiation of an appellate waiver during sentencing
raises many of the same concerns as a district court’s partici-
pation in plea negotiations.
[3] We have explained previously that judicial participa-
tion in plea negotiations is prohibited, first, because it “inevi-
tably carries with it the high and unacceptable risk of coercing
a defendant to accept the proposed agreement and plead
guilty;” second, because it threatens the integrity of the judi-
cial process; and finally, because it may affect the judge’s
impartiality after negotiations are completed. Bruce, 976 F.2d
at 556-58. These same concerns arise when appellate waivers
are at issue. First, judicial participation in appellate-waiver
negotiations during sentencing carries with it a high risk of
coercing a defendant to accept the waiver, raising questions
about whether the waiver “was the product of a free and
deliberate choice rather than coercion or improper induce-
ment.” Doe, 155 F.3d at 1074. “It is the discretion to impose
either a lenient or lengthy sentence that lies at the heart of the
coercive potential inherent when a judge participates in plea
negotiations.” United States v. Markin, 263 F.3d 491, 498 (6th
Cir. 2001). That discretion makes a judge’s active participa-
tion in appellate-waiver negotiations inherently coercive.
Second, “ ‘[t]he unequal positions of the judge and the
accused . . . raise a question of fundamental fairness’ regard-
less of the degree or type of judicial involvement.” Bruce, 976
F.2d at 557 (citation omitted) (alterations in original). Instead,
“[t]he judge’s role must be that of a neutral arbiter of the
criminal prosecution: his involvement in the adversary pro-
cess . . . is beyond and detracts from that judicial duty.” Id.
In the context of appellate waivers, that concern is exacer-
bated because such a waiver insulates the court’s decision
from review. Indeed, if district courts could directly negotiate
valid appellate waivers, we would be entirely deprived of our
UNITED STATES v. GONZALEZ-MELCHOR 9153
error-correcting and error-preventing functions. See generally
Steven Shavell, The Appeals Process as a Means of Error
Correction, 24 J. Legal Stud. 379, 425-26 (1995) (describing
the functions and purposes of the appellate process as correct-
ing error, harmonizing the law among trial courts, preventing
error by inducing trial judges to make fewer errors or risk
reversal, and lending legitimacy to the legal process).
Finally, allowing a district court to engage in appellate-
waiver negotiations at sentencing threatens the judge’s impar-
tiality after negotiations are completed. In the context of plea-
agreement negotiations, we have noted that judicial involve-
ment compromises the judge’s decision making because it
“ ‘makes it difficult for a judge to objectively assess the vol-
untariness of the plea eventually entered by the defendant,”
and if plea discussions ultimately fail and the case proceeds
to trial, the judge may view unfavorably the defendant’s rejec-
tion of the proposed agreement. Bruce, 976 F.2d at 557-58
(citation omitted). Similarly, a judge who participates in
appellate-waiver negotiations loses his or her ability to objec-
tively assess the voluntariness of the waiver, and may view
unfavorably a rejection of the waiver and take that rejection
into account at sentencing.
In United States v. Markin, the Sixth Circuit reached a sim-
ilar conclusion, holding that the rationales underlying Rule
11(c)(1) apply to judicial negotiation of a waiver in exchange
for consideration at sentencing. 263 F.3d at 498. In Markin,
the defendant contended that the district court had improperly
negotiated with him at sentencing to waive objections to the
presentence report. Id. at 493-94. Because the defendant’s
guilty plea had been entered and accepted before the disputed
interaction occurred, the district court’s participation did not
expressly violate Rule 11(c)(1). Id. at 496. Nevertheless, the
court concluded, “We are . . . troubled by a district court’s
participation in sentencing discussions in which a criminal
defendant offers to waive a legal argument in return for con-
sideration in sentencing.” Id. at 497. The court continued:
9154 UNITED STATES v. GONZALEZ-MELCHOR
It is the discretion to impose either a lenient or
lengthy sentence that lies at the heart of the coercive
potential inherent when a judge participates in plea
negotiations. In our view, this rationale applies with
equal force whether the judge is negotiating an
agreement to plead guilty or an agreement to waive
objections to the presentence report in return for con-
sideration at sentencing.
Id. at 498 (internal citation omitted). Reviewing the transcript,
however, the Markin court found no reversible error because
“the transcript of the entire status conference, including the
district court’s consistent refusal to commit to a sentence and
the lack of any agreement between the parties belies the con-
tention that any kind of agreement was reached during the sta-
tus conference.” Id.
Here, in contrast, an agreement clearly was reached. The
district court initiated negotiations by telling Gonzalez-
Melchor’s counsel that an appeal to the Ninth Circuit would
be “a long-shot” and he wanted to hear Gonzalez-Melchor
say, “ ‘I’ll accept the judgments of this court. I’m not going
to waste anybody else’s time and money.’ ” If Gonzalez-
Melchor said those things, the court continued, he would
receive a sentence “somewhere in the range of 60, 65
months,” below the Sentencing Guidelines’ recommended
range. Gonzalez-Melchor responded by waiving his right to
appeal, and the district court imposed a below-Guidelines sen-
tence within the promised range.
[4] This unusual and potentially coercive situation—a
waiver of appellate rights negotiated by the district court dur-
ing sentencing—implicates the same concerns Rule 11(c)(1)
seeks to remedy. The negotiation was potentially coercive
because of “ ‘[t]he unequal positions of the judge and the
accused,’ ” Bruce, 976 F.2d at 557 (citation omitted), and that
potential was especially high because Gonzalez-Melchor had
to decide immediately whether to waive his appellate rights,
UNITED STATES v. GONZALEZ-MELCHOR 9155
see Anderson, 993 F.2d at 1438. Moreover, because the dis-
trict court directly negotiated the waiver, its inquiry into
whether the waiver was voluntary does not allay our concerns.
See id.
[5] Given the coercive potential in a district court’s power
to impose a lengthy or lenient sentence, we are “troubled by
a district court’s participation in sentencing discussions in
which a criminal defendant offers to waive a legal argument
in return for consideration in sentencing.” Markin, 263 F.3d
at 497. We hold that the appellate waiver, negotiated by the
district court in exchange for a reduced sentence, is invalid
and unenforceable.
VACATED AND REMANDED.