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-

M LAB-1 ANUEL GONZALEZ-MELCHOR,

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
COUNSEL

Kristi A. Hughes, Federal Public Defender, San Diego, California, 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.

UNITED STATES v. GONZALEZ-MELCHOR 9143
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. GonzalezMelchor 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, California approximately one mile north of the United StatesMexico 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, GonzalezMelchor appeared before an IJ for a group deportation hearing. At that hearing, Gonzalez-Melchor admitted that he pre9144 UNITED STATES v. GONZALEZ-MELCHOR
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 qualify, 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 voluntary departure. For the rest of you, I see bad facts

which tells me you don’t deserve voluntary departure. 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

UNITED STATES v. GONZALEZ-MELCHOR 9145
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 acceptance 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 counsel:

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 con9146 UNITED STATES v. GONZALEZ-MELCHOR
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 anymore, that he isn’t, that he promises 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 pursue 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)

UNITED STATES v. GONZALEZ-MELCHOR 9147
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 lawyer 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?

9148 UNITED STATES v. GONZALEZ-MELCHOR
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 defendant who has signed an appellate waiver, although “ ‘we will

not exercise that jurisdiction to review the merits of [a defendant’s] appeal if we conclude that she knowingly and voluntarily 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)

UNITED STATES v. GONZALEZ-MELCHOR 9149
(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 inducement.” 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 defendant cannot be said to have knowingly and voluntarily relinquished 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 rendered 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 finding of judicial misconduct in connection with a plea proceeding 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

9150 UNITED STATES v. GONZALEZ-MELCHOR
States v. Bruce, 976 F.2d 552, 557 (9th Cir. 1992). Accordingly, Rule 11(b)(1)(N) requires that, “[b]efore the court

accepts a plea of guilty . . . the court must address the defendant 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 “responses to the judge’s questioning during the formalistic colloquy 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 pressured 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 discussions took place. See, e.g., Bruce, 976 F.2d at 556 (stating that

the rule “simply commands that the judge not participate in,

UNITED STATES v. GONZALEZ-MELCHOR 9151
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 participation in plea negotiations. 

[3] We have explained previously that judicial participation in plea negotiations is prohibited, first, because it “inevitably 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 judicial 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 inducement.” 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 participation in appellate-waiver negotiations inherently coercive. 

Second, “ ‘[t]he unequal positions of the judge and the

accused . . . raise a question of fundamental fairness’ regardless 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 process . . . is beyond and detracts from that judicial duty.” Id.

In the context of appellate waivers, that concern is exacerbated 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

9152 UNITED STATES v. GONZALEZ-MELCHOR
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 correcting 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 appellatewaiver negotiations at sentencing threatens the judge’s impartiality after negotiations are completed. In the context of pleaagreement negotiations, we have noted that judicial involvement compromises the judge’s decision making because it

“ ‘makes it difficult for a judge to objectively assess the voluntariness 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 rejection 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 objectively 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 similar 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 consideration in sentencing.” Id. at 497. The court continued:

UNITED STATES v. GONZALEZ-MELCHOR 9153
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 consideration 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 contention that any kind of agreement was reached during the status conference.” Id.

Here, in contrast, an agreement clearly was reached. The

district court initiated negotiations by telling GonzalezMelchor’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 GonzalezMelchor 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 sentence within the promised range. 

[4] This unusual and potentially coercive situation—a

waiver of appellate rights negotiated by the district court during 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,

9154 UNITED STATES v. GONZALEZ-MELCHOR
see Anderson, 993 F.2d at 1438. Moreover, because the district 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.

UNITED STATES v. GONZALEZ-MELCHOR 9155