FILED

United States Court of Appeals

Tenth Circuit

June 10, 2015

Elisabeth A. Shumaker

Clerk of Court

PUBLISH

UNITED STATES COURT OF APPEALS

TENTH CIRCUIT

UNITED STATES OF AMERICA, 

Plaintiff-Appellee,

v.

TIMOTHY JOHN VANDERWERFF, 

Defendant-Appellant.

------------------------------

BLAIN D. MYHRE,

Amicus Curiae. 

No. 13-1227

Appeal from the United States District Court

for the District of Colorado

(D.C. No. 1:12-CR-00069-JLK-1)

O. Dean Sanderford, Assistant Federal Public Defender, Denver, Colorado

(Virginia L. Grady, Interim Federal Public Defender, Denver, Colorado, with him

on the brief), for Defendant-Appellant.

James C. Murphy, Assistant United States Attorney, Denver, Colorado (John F.

Walsh, United States Attorney, Denver, Colorado, with him on the brief), for

Plaintiff-Appellee.

Blain David Myhre, Blain Myhre, LLC, Englewood, Colorado, as Amicus Curiae.

Before LUCERO, HARTZ, and HOLMES, Circuit Judges.

Appellate Case: 13-1227 Document: 01019442711 Date Filed: 06/10/2015 Page: 1 
HOLMES, Circuit Judge.

Defendant-Appellant Timothy Vanderwerff appeals from his conviction and

sentence for receipt of child pornography, arguing that the district court erred in

rejecting his initial (first) plea agreement with the government because it

contained an appellate waiver. The government agrees with Mr. Vanderwerff, as

does an appointed amicus counsel, and all parties urge reversal and remand for resentencing. Having thoroughly considered the matter, we also agree that such

relief is appropriate. Specifically, we conclude that the district court’s rejection

of Mr. Vanderwerff’s plea agreement was premised on legally erroneous and

irrelevant considerations; consequently, its action constituted an abuse of

discretion. Exercising our jurisdiction under 28 U.S.C. § 1291, we reverse and

remand this case, instructing the district court to vacate its judgment and

sentence, to permit Mr. Vanderwerff to withdraw his guilty plea, and to conduct

further proceedings not inconsistent with this opinion. 

I

In February 2012, a federal grand jury indicted Mr. Vanderwerff for three

child-pornography-related offenses in the United States District Court for the

District of Colorado. Count 1 charged Mr. Vanderwerff with receipt of child

pornography in violation of 18 U.S.C. § 2252A(a)(2)(A), and Counts 2 and 3

charged him with possessing child pornography in violation of 18 U.S.C.

2

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§ 2252A(a)(5)(B). 

Mr. Vanderwerff and the government entered into a plea agreement. Under

the agreement, Mr. Vanderwerff would plead guilty to Count 2 and the

government would dismiss Counts 1 and 3. Mr. Vanderwerff also promised not to

seek a departure or variance under the United States Sentencing Guidelines

Manual (“U.S.S.G.” or “the Guidelines”) or to request a sentence of less than five

years. For its part, in addition to offering to dismiss Counts 1 and 3, the

government committed itself to submitting a motion to the district court to grant

Mr. Vanderwerff credit for acceptance of responsibility pursuant to U.S.S.G.

§ 3E1.1 if Mr. Vanderwerff’s behavior warranted the adjustment. Most relevant

to the instant appeal, the plea agreement included a provision by which Mr.

Vanderwerff waived his right to appeal.1

As a result of this initial plea agreement, Mr. Vanderwerff faced a statutory

1 Although the waiver of appellate rights was broad, it was not

absolute. The pertinent text of the waiver read:

[T]he defendant knowingly and voluntarily waives the right to

appeal any matter in connection with this prosecution,

conviction, or sentence unless it meets one of the following three

criteria: (1) the sentence imposed is above the maximum penalty

provided in the statute of conviction, (2) the Court, after

determining the otherwise applicable sentencing guideline range,

either departs or varies upwardly, or (3) the Court determines

that the offense level is greater than that calculated by the parties

below and imposes a sentence based upon that higher offense

level determination. 

Supp. R. at 6 (Plea Agreement, dated Apr. 10, 2012).

3

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sentencing range of zero to ten years of imprisonment. See 18 U.S.C.

§ 2252A(b)(2) (providing for a sentence of “not more than 10” years for violating

§ 2252A(a)(5), as alleged in Count 2). 

At an initial change-of-plea hearing, the district court declined to either

accept or reject the plea. After listening to arguments from both parties in favor

of the plea, the district court cited an ostensible “tectonic shift in our

jurisprudence” brought about by the Supreme Court’s decision in Lafler v.

Cooper, --- U.S. ----, 132 S. Ct. 1376 (2012). R., Vol. III, at 10 (Change-of-Plea

Hr’g Tr., dated Apr. 10, 2012). The court found that Lafler suggested that a

sentencing court should be “a participant in the plea-bargaining process” and

renounce “the judicial branch[’s prior] . . . Pontius Pil[ate] attitude about plea

bargains.” Id. at 10–11. The district court further found that the ultimate

sentence should only have as its predicate “the criteria listed in [18

U.S.C. §] 3553” and suggested that Mr. Vanderwerff’s plea agreement—which,

notably, contained an appellate waiver—might violate those criteria. Id. at 11.

The district court then offered some thoughts on plea bargaining in general,

which it cautioned were not going to be “determinative” of its ruling but which

constituted a “continuing concern.” Id. at 11–12. In this regard, the district court

opined as to “the significant disrepute that obsessive plea bargaining has in this

country” and indicated that it had “to pay attention to that.” Id. at 12. 

The district court then returned to the subject of 18 U.S.C. § 3553(a)’s

4

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sentencing factors and specifically focused on the role those factors purportedly

should play in its consideration of the propriety of the appellate waiver in Mr.

Vanderwerff’s plea agreement. Significantly, the court perceived a nexus

between its task in accepting or rejecting appellate waivers and our court’s

responsibilities in reviewing trial judges’ discretionary sentencing determinations

under § 3553(a). In this regard, it stated: 

One of the things that concerns me, deeply, is the language in

some of the 10th Circuit cases, which suggests, to me, that the

Judges on the 10th Circuit are not paying attention to their

obligations in reviewing the decisions of Judges of the District

Court. I have said that in the [Aguirre]

[2] case, [in] what is, I

hope, a more diplomatic way than I just said it now. . . . 

[Section] 3553[] seems, to me, . . . A, exclusive; and B,

determinative of whether or not a waiver can be accepted.

R., Vol. III, at 12–13 (emphasis added). In light of these considerations, the

district court ordered the parties to submit supplemental briefs “on the application

of the [§] 3553 factors to this particular sentence of this particular case.” Id. at

13. 

After reviewing the parties’ supplemental briefs, the district court rejected

the plea agreement. The court began its ruling by noting the decrease in criminal

trials and the growth in guilty pleas—phenomena that it bemoaned. Then, turning

to the plea bargain at hand, the district court found the dismissal of Counts 1 and

3 in return for the guilty plea to Count 2 “not unconscionable” and concluded as a

2 United States v. Aguirre, No. 11-CR-00149-JLK, 2011 WL 3036126

(D. Colo. July 25, 2011).

5

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result that it was “appropriate to defer to prosecutorial discretion” regarding the

charge bargain.3

 R., Vol. I, at 45 (Order, filed June 28, 2012). However, the

district court rejected the appellate waiver as “unjustified.” Id. 

The court observed that “[i]n the wake of the Supreme Court’s holding that

the [Guidelines] are merely advisory, not mandatory, see United States v. Booker,

543 U.S. 220, 247 (2005), no circuit court has revisited the enforceability of

appellate waivers.” R., Vol. I, at 43. According to the court, “[s]entencing,

post-Booker, requires a trial court to consider context and to apply criteria rather

than perform a mechanical or clerical entry of a matrixed judgment.” Id. It thus

reasoned that this post-Booker sentencing regime called for courts to proceed

cautiously and selectively in approving appellate waivers: 

The responsibility of appellate review is to decide how well the

sentencing judge has established the sentence within this

described discipline. That is fundamentally dissimilar to the

pre-Booker function of determining whether an arithmetic

calculation has been executed correctly. Rather, reviewing

sentences under an abuse of discretion standard is a complex

inquiry meant to assure that the judicial administration of justice

is relevant to the values and expectations of society.

Indiscriminate acceptance of appellate waivers undermines the

ability of appellate courts to ensure the constitutional validity of

convictions and to maintain consistency and reasonableness in

sentencing decisions. . . . Thus, such waivers should only be

included where they are justified by the facts and circumstances

of a particular case.

3 As discussed infra, “charge bargains” are “predicated on the

dismissal of some counts” in the indictment. United States v. Robertson, 45 F.3d

1423, 1437 (10th Cir. 1995).

6

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Id. at 44. The court ultimately concluded that Mr. Vanderwerff’s waiver was not

so justified. 

The district court acknowledged the parties’ view that our precedent

generally supported the use of appellate waivers, inasmuch as we have found

them beneficial to the criminal justice system and its various actors, but

concluded that this general perspective on appellate waivers was “irrelevant to

[its] determination of whether an appellate waiver is justified in the context of

this case.” Id. at 45. The court was similarly unimpressed with the litigants’

“case-specific” explanations, id., for the waiver—which, notably, they made

under the rubric of § 3553(a) because the court required them to do so. The court

rejected the government’s argument that Mr. Vanderwerff’s appellate waiver

evidenced his acceptance of responsibility and remorse because it “ignore[d] the

nature of Mr. Vanderwerff’s bargain,” especially the significant benefit he was

receiving “[i]n exchange for” the waiver. Id. at 46. Likewise, the court found

unpersuasive the parties’ argument that “the dismissal of charges 1 and 3 w[ould]

result in a statutory sentencing range that better accommodates the interests of

justice and the strictures of 18 U.S.C. § 3553.” Id. Specifically, envisioning a

nexus between the § 3553(a) factors and the propriety of the appellate waiver, the

court opined: “[T]he parties seek to limit Mr. Vanderwerff’s sentence to a range

of five to ten years of incarceration. Although these sentencing consequences

may have induced Mr. Vanderwerff to accept the government’s plea bargain, they

7

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do not justify including an appellate waiver.” Id. (emphasis added). The district

court concluded that “[t]he interests of justice . . . are best served by permitting

the calm and deliberate review by the Court of Appeals” of the sentence. Id. Mr.

Vanderwerff sought review of the court’s action regarding the plea agreement, but

we dismissed the appeal for lack of jurisdiction, concluding that it was premature.

The parties then negotiated a new plea agreement. The new deal omitted

the appellate waiver and stipulated to the dismissal of Counts 2 and 3 (instead of

Counts 1 and 3), leaving only Count 1, a receipt count, for purposes of the guilty

plea. Because this changed the offense designated for entry of the guilty plea

from possession to receipt of child pornography, Mr. Vanderwerff’s statutory

sentencing range increased from zero to ten years, as contemplated by the initial

plea agreement, to five to twenty years. See 18 U.S.C. § 2252A(b)(1). In other

words, under the new plea agreement, Mr. Vanderwerff was subject to potentially

greater statutory penalties—a five-year mandatory minimum and a higher

maximum of twenty years. 

The government did commit in the new plea agreement to seek a sentence

reduction for acceptance of responsibility and to urge the district court to impose

a sentence of no more than twelve years in prison. The new agreement also

included a provision reserving to Mr. Vanderwerff the right to appeal from the

district court’s earlier rejection of the first plea agreement. The district court

accepted the new plea agreement, whereupon it reiterated that it had rejected the

8

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earlier appellate waiver because the “Section 3553 factors are exclusive” and the

waiver was not “tied into those exclusive sentencing factors.” R., Vol. IV, at 21

(Change-of-Plea Hr’g Tr., dated Aug. 9, 2012).

The presentence report (“PSR”) confirmed the statutory minimum and

maximum, as embodied in the plea agreement, and calculated an advisory

Guidelines range of 188 to 235 months in prison.4

 However, the PSR

recommended a downward variance to 108 months in light of Mr. Vanderwerff’s

conduct, advanced age, and physical and mental health. The government

proposed a sentence of 144 months instead. The district court ultimately adopted

the PSR’s recommendation and imposed a sentence of 108 months. Mr.

Vanderwerff timely appealed.

On appeal, the government agrees with Mr. Vanderwerff that the district

court abused its discretion in rejecting the first plea agreement, and it joins Mr.

Vanderwerff’s request for reversal. To ensure a full and comprehensive

consideration of the issues raised by this appeal, we appointed pro bono amicus

counsel to submit a brief expressing an “independent assessment of the legal

propriety of the district court’s challenged sentence decision.” Order, No. 13-

1227, at 2 (10th Cir., filed Mar. 25, 2014). Amicus counsel filed that brief on

May 2, 2014; counsel agreed with the parties that the district court’s conduct

4 In preparing the PSR, the United States Probation Office utilized the

2012 edition of the Guidelines.

9

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amounted to an abuse of discretion.

II

Mr. Vanderwerff contends that the district court abused its discretion by

rejecting the first plea agreement because it contained an appellate waiver. We

review a district court’s decision not to accept a plea agreement for abuse of

discretion. See United States v. Veri, 108 F.3d 1311, 1314 (10th Cir. 1997);

Robertson, 45 F.3d at 1437; see also United States v. Rakes, 510 F.3d 1280, 1286

(10th Cir. 2007) (“A district court enjoys substantial discretion in deciding

whether to accept or reject a plea agreement . . . .”). “A district court abuses its

discretion if its adjudication of a claim is based upon an error of law . . . .” 

United States v. Crowe, 735 F.3d 1229, 1244 (10th Cir. 2013), cert. denied, ---

 U.S. ----, 134 S. Ct. 1565 (2014); see United States v. Battle, 706 F.3d 1313,

1317 (10th Cir. 2013) (“A district court abuses its discretion when it relies on an

incorrect conclusion of law . . . .”); Westar Energy, Inc. v. Lake, 552 F.3d 1215,

1224 (10th Cir. 2009) (“An abuse of discretion occurs when the district court

commits an error of law . . . .”); cf. United States v. Nacchio, 555 F.3d 1234, 1276

(10th Cir. 2009) (en banc) (McConnell, J., dissenting) (“This court has held time

and time again that a district court abuses its discretion if it applies the wrong

legal standard.”). Similarly, when a district court predicates its ruling on an

“improper and irrelevant factor,” this error “provides a strong indication that the

district court abused its discretion.” Rio Grande Silvery Minnow v. Bureau of

10

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Reclamation, 601 F.3d 1096, 1132 (10th Cir. 2010). 

We conclude that the district court’s rejection of Mr. Vanderwerff’s initial

plea agreement because it contained an appellate waiver was premised on legally

erroneous and irrelevant considerations and, consequently, that this action

amounted to an abuse of discretion. We begin by providing a brief overview of

the law of plea bargains and then turn to our analysis of the bases for the district

court’s decision. 

A 

The “starting point” for an inquiry into a district court’s rejection of a

guilty plea is Rule 11 of the Federal Rules of Criminal Procedure. Robertson, 45

F.3d at 1437. Rule 11 provides: “An attorney for the government and the

defendant’s attorney . . . may discuss and reach a plea agreement.” Fed. R. Crim.

P. 11(c)(1). The district court may then either accept or reject that agreement in

its substantial discretion, “[b]ut that discretion is not without limit.” Rakes, 510

F.3d at 1286. 

Plea bargains are commonly either “charge bargains,” where the prosecutor

agrees to drop some charges in exchange for a guilty plea on others, or “sentence

bargains,” where the prosecutor agrees to support, or at least not oppose, a

particular sentence. Robertson, 45 F.3d at 1437. Courts enjoy considerable

discretion in their consideration of sentence bargains because “the prosecution’s

role . . . is strictly advisory,” but judicial discretion is more limited with respect

11

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to charge bargains because such bargains “are primarily a matter of discretion for

the prosecution” and the “court’s sentencing discretion is implicated only as an

incidental consequence of the prosecution’s exercise of executive discretion.” Id.

at 1437–38; see also United States v. Miller, 722 F.2d 562, 565 (9th Cir. 1983)

(warning that “courts should be wary of second-guessing prosecutorial choices”

because they “do not know which charges are best initiated at which time, which

allocation of prosecutorial resources is most efficient, or the relative strengths of

various cases and charges” (citations omitted)). 

We have previously stated that in charge bargains, “a court’s sentencing

discretion is implicated . . . in precisely the same manner it is implicated by

prosecutorial decisions to bring charges in the first place, where prosecutorial

discretion is nearly absolute.” Robertson, 45 F.3d at 1438 (emphasis added). 

“Thus, while district courts may reject charge bargains in the sound exercise of

judicial discretion, concerns relating to the doctrine of separation of powers

counsel hesitancy before second-guessing prosecutorial choices.” Id.

The parties and amicus counsel all agree that the plea agreement at issue

here is properly characterized as a charge bargain. In that regard, the agreement

indicated that “the government may recommend any term of imprisonment up to

the statutory maximum for the offense of conviction.” Supp. R. at 3. 

Furthermore, as is typical of a charge bargain, the agreement was predicated on

the dismissal of charges (i.e., Counts 1 and 3) in exchange for a guilty plea to

12

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another charge (i.e., Count 2). See United States v. Carrigan, 778 F.2d 1454,

1462 (10th Cir. 1985) (“[C]harge bargains[] [are] predicated on the dismissal of

other charges . . . .”); accord Robertson, 45 F.3d at 1437.

The district court did not seriously object to the specific terms of the

charge bargain in the parties’ first plea agreement—which included the

government’s agreement to dismiss a possession and a receipt count in exchange

for Mr. Vanderwerff’s agreement to plead guilty to a possession count (i.e., Count

2). However, following the court’s rejection of the appellate-waiver component

of the plea agreement, the agreement itself could not be sustained and the court

denied it in its entirety. The parties subsequently arrived at another plea

agreement, but the government was apparently unwilling, absent the appellate

waiver, to offer the same bargain regarding the charges. The bargain it offered

subjected Mr. Vanderwerff to potentially more severe penalties, involving a fiveyear mandatory minimum and a twenty-year statutory maximum.

We now examine the considerations that animated the district court’s

decision to reject the appellate waiver. We are constrained to conclude that those

considerations were legally erroneous and irrelevant. Accordingly, the district

court abused its discretion. 

B

1

The district court’s reliance on the Supreme Court’s decision in Lafler as a

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basis for rejecting the appellate waiver in Mr. Vanderwerff’s first plea agreement

evinces a serious misunderstanding of that case. The district court referred to

Lafler as effecting a “tectonic shift in our jurisprudence,” R., Vol. III, at 10;

accord id., Vol. IV, at 21, regarding the constitutional salience of the pleabargaining process and the district courts’ role in it. Specifically, the court noted

that Lafler “raise[d] plea bargaining to the level of constitutional scrutiny,” id.,

Vol. IV, at 21, and also suggested that trial courts should be “a participant in the

plea-bargaining process,” id., Vol. III, at 10. Apparently, the court reasoned that

these features of Lafler gave the court greater leeway to scrutinize and reject the

appellate waiver in Mr. Vanderwerff’s plea agreement. However, the court

grievously misread Lafler’s import. And, consequently, its rejection of the

waiver was predicated on an error of law and amounted to an abuse of discretion. 

First and foremost, Lafler was a case relating to ineffective assistance of

counsel in the plea-bargaining process—not the matters addressed by the district

court. Shortly after it was issued, we had occasion to summarize Lafler’s ruling:

“Lafler held that an attorney who rendered constitutionally deficient advice to

reject a plea bargain was ineffective where his advice caused his client to reject

the plea and go to trial, only to receive a much harsher sentence.” In re Graham,

714 F.3d 1181, 1182 (10th Cir. 2013) (per curiam); see also United States v.

Moya, 676 F.3d 1211, 1214 (10th Cir. 2012) (interpreting Lafler as speaking to

the standards governing ineffective assistance of counsel). 

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Even in this specific ineffective-assistance area, Lafler did not purport to

dramatically break new ground. As we observed in discussing the case, “the

Court reached its decision by applying the well-established principles regarding

the assistance of counsel that were initially set forth in Strickland v. Washington,

[466 U.S. 668 (1984)].” Graham, 714 F.3d at 1182–83; see also Hare v. United

States, 688 F.3d 878, 879 (7th Cir. 2012) (holding that in Lafler, “the Court’s

language repeatedly and clearly spoke of applying an established rule to the

present facts”); In re Perez, 682 F.3d 930, 932 (11th Cir. 2012) (per curiam)

(noting that Lafler is “merely an application of the Sixth Amendment right to

counsel, as defined in Strickland, to a specific factual context”). 

To be sure, Lafler did acknowledge in support of its holding that plea

bargaining plays a critical role in the criminal justice system. See 132 S. Ct. at

1388 (rejecting the petitioner’s argument that “[a] fair trial wipes clean any

deficient performance by defense counsel during plea bargaining” because “[t]hat

position ignores the reality that criminal justice today is for the most part a

system of pleas, not a system of trials”); see also Missouri v. Frye, --- U.S. ----,

132 S. Ct. 1399, 1407 (2012) (acknowledging that plea bargaining is “central to

the administration of the criminal justice system”). However, with a nod to the

district court’s tectonic-shift metaphor, we find it patent that this understanding

of plea bargaining’s importance is hardly earth-shaking news. Furthermore,

contrary to the district court’s reasoning, we discern nothing in Lafler to suggest

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that it introduced a new role for trial courts in the plea-bargaining process, let

alone one that would make the judiciary a more active player in that process. 

In sum, the district court’s reading of Lafler is, at bottom, untenable:

nothing in that decision dramatically pushed the plea-bargaining process into the

constitutional limelight or purported to alter the role of the trial judge in that

process. Accordingly, the district court could not reasonably glean from Lafler a

greater license to reject the appellate waiver in Mr. Vanderwerff’s plea

agreement. Insofar as this rejection was predicated on the district court’s

misreading of Lafler, it constituted an error of law and an abuse of discretion. 

2

The district court also justified its rejection of the appellate waiver in Mr.

Vanderwerff’s first plea agreement on the ground that the enforceability of

appellate waivers had been placed in doubt by Booker. It suggested that Booker

called upon courts to “revisit[ ] the enforceability of appellate waivers,” R., Vol.

I, at 43, and, more specifically, to act cautiously and selectively when

entertaining requests from litigants to approve them. This is so, reasoned the

court, because Booker gave trial courts discretion in applying sentences, and

appellate review is necessary to determine whether those courts are properly

exercising their discretion. Notably, as it did in its reading of Lafler, the district

court seemingly construed Booker as obliging it to exercise a wider scope of

discretion in scrutinizing and rejecting appellate waivers. However, the district

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court has unfortunately failed to divine the true substance of Booker. This

misunderstanding engendered legal error because the court at least partly based its

rejection of Mr. Vanderwerff’s appellate waiver on it. The court thereby abused

its discretion. 

Booker’s core holding is that the Guidelines are advisory. See 543 U.S. at

245 (“So modified, the federal sentencing statute makes the Guidelines effectively

advisory.” (citation omitted)); see also, e.g., Gall v. United States, 552 U.S. 38,

46 (2007) (“As a result of our decision [in Booker], the Guidelines are now

advisory . . . .”); United States v. Haggerty, 731 F.3d 1094, 1098 n.2 (10th Cir.

2013) (“Booker . . . explains [that] the Guidelines are merely advisory . . . .”);

United States v. Perez-Jiminez, 654 F.3d 1136, 1144 (10th Cir. 2011) (“The

Supreme Court’s decision in United States v. Booker rendered the Guidelines

advisory.” (citation omitted)). There is nothing in Booker that speaks to appellate

waivers at all. Indeed, the only discussion of plea bargaining in Booker is the

neutral comment that after that decision, “[p]rosecutors and defense attorneys

would still resolve the lion’s share of criminal matters through plea bargaining.” 

543 U.S. at 248. The fact that the Guidelines are no longer mandatory after

Booker has no evident connection to appellate waivers one way or the other. 

Indeed, one cannot logically infer from Booker’s grant of additional

sentencing discretion to trial courts, on the one hand, the imposition of an

obligation on those courts, on the other, to restrict a defendant’s ability to

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knowingly and voluntarily waive his or her appellate rights. If the Court was

concerned in Booker that trial courts’ discretionary sentencing decisions would be

insulated from appellate review by appellate waivers—a proposition that we

doubt, for the reasons noted infra—it did not even intimate this, much less

explicitly issue a ruling to redress the purported concern. Operating on a blank

slate, we would be disinclined absent any textual foothold in Booker to conclude

that the Court contemplated such a ruling. Cf. Cressman v. Thompson, 719 F.3d

1139, 1156 (10th Cir. 2013) (“Circuit courts should be very careful to suggest the

Supreme Court has implicitly reversed itself, especially because, of course, the

Court can and should speak for itself.”); Levine v. Heffernan, 864 F.2d 457, 461

(7th Cir. 1988) (“Lower courts . . . , out of respect for the great doctrine of stare

decisis, are ordinarily reluctant to conclude that a higher court precedent has been

overruled by implication.”). Fortunately, however, the slate is not free from

helpful markings. 

Though we apparently have never examined the merits of the precise

reading of Booker that the district court embraced—viz., that Booker obliges trial

courts to restrict the approval of appellate waivers because of concern that the

waivers might insulate judges’ discretionary sentencing decisions from appellate

review—the district court was mistaken when it asserted that “no circuit court has

revisited the enforceability of appellate waivers” in light of Booker. R., Vol. I, at

43. Indeed, the Fifth Circuit rejected a construction of Booker analogous to the

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one the district court espoused here. See United States v. Oliver, 630 F.3d 397,

414–15 (5th Cir. 2011). There, the defendant argued that the appellate waiver in

his plea agreement violated Booker because “it [wa]s over broad.” Id. at 414. 

This was apparently so because the waiver had the effect of shielding the

sentencing court’s discretionary reasonableness analysis—which is permissible

post-Booker—from appellate review. The Fifth Circuit summarized the

defendant’s argument in this regard: “Without citing any authority, Oliver states

that an appeal waiver that prevents a defendant from challenging his sentence on

any ground, including reasonableness, violates Booker.” Id. Then the court

proceeded to make short work of that argument, summarily rejecting it as follows:

“Contrary to Oliver’s assertion, nothing in Booker prohibits appeal waivers.” Id.

at 414–15. In other words, the Oliver court quickly dispatched the notion that

Booker somehow invalidated appellate waivers insofar as they insulated a district

court’s discretionary sentencing decisions from appellate review. Like the Oliver

court, we are not inclined to accept the district court’s view that, for similar

reasons, Booker imposed an obligation on trial courts to carefully scrutinize and

restrict approval of appellate waivers. 

Indeed, we have routinely enforced appellate waivers in the post-Booker

era. See, e.g., United States v. Garcia-Ramirez, 778 F.3d 856, 857 (10th Cir.

2015) (per curiam); United States v. Tanner, 721 F.3d 1231, 1233 (10th Cir.

2013) (per curiam); United States v. Cudjoe, 634 F.3d 1163, 1164–65 (10th Cir.

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2011); United States v. Leyva-Matos, 618 F.3d 1213, 1215 (10th Cir. 2010). And

so have other circuits. See, e.g., United States v. Adams, 780 F.3d 1182, 1183

(D.C. Cir. 2015); United States v. Purser, 747 F.3d 284, 286 (5th Cir.), cert.

denied, --- U.S. ----, 135 S. Ct. 403 (2014); United States v. Grimes, 739 F.3d

125, 126 (3d Cir. 2014); United States v. Brizan, 709 F.3d 864, 866 (9th Cir.

2013); United States v. Copeland, 707 F.3d 522, 524 (4th Cir. 2013); United

States v. Guzman, 707 F.3d 938, 939 (8th Cir. 2013); United States v. Toth, 668

F.3d 374, 374 (6th Cir. 2012); United States v. Kilcrease, 665 F.3d 924, 926 (7th

Cir. 2012); United States v. Arevalo, 628 F.3d 93, 94 (2d Cir. 2010); United

States v. Segarra, 582 F.3d 1269, 1273 (11th Cir. 2009) (per curiam); United

States v. Soto-Cruz, 449 F.3d 258, 259 (1st Cir. 2006). This caselaw suggests that

Booker has not cast a shadow (even tacitly) on the propriety of appellate waivers.

In sum, in our view, the district court misread Booker and committed legal

error when it used that case to partly justify its decision to reject Mr.

Vanderwerff’s appellate waiver. In this respect, the court abused its discretion.

3

The district court similarly erred as a matter of law in making 18 U.S.C.

§ 3553(a) a mainstay of its rationale for rejecting Mr. Vanderwerff’s appellate

waiver. The district court assigned great weight to the § 3553(a) factors in

rejecting the waiver. See R., Vol. IV, at 21 (“[The] Section 3553 factors are

exclusive in sentencing and form the basis for my not accepting the earlier

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proposed plea disposition with a waiver of right to appeal because it wasn’t tied

into those exclusive sentencing factors.”). However, as we see it, ordinarily, the

§ 3553(a) factors should play no direct role in a district court’s determination of

whether to accept or reject an appellate waiver in a plea agreement.

In its very title, § 3553(a) indicates that its “[f]actors [are] to be considered

in imposing a sentence.” 18 U.S.C. § 3553(a) (emphasis added). Thus, the

customary and obvious province for operation of these factors is the sentencing

phase of criminal proceedings, not the entry-of-guilty-plea phase. In our view,

the district court committed legal error by effectively mapping the sentencing

factors of § 3553(a) onto the rubric for determining whether to accept or reject a

plea agreement that contains an appellate waiver. As the government succinctly

put it, the court’s “requirement that appeal waivers be justified under § 3553(a)

confuses a defendant’s substantive right to a fair determination of his sentence[]

with the procedural right to seek further review of that sentence.” Aplee. Br. at

16. 

Notably, the district court’s approach was seemingly animated by concerns

that are of the same or similar stripe as those at work in the court’s misguided

reading of Lafler and Booker. Specifically, by incorporating the § 3553(a) factors

into the process for accepting and rejecting plea agreements containing appellate

waivers, the court ostensibly sought to ensure (to the extent that it could) that our

court maintained an opportunity to review the propriety of trial judges’

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applications of § 3553(a)’s sentencing factors—viz., that we had a chance to

review the legal soundness of trial judges’ post-Booker exercises of discretionary

sentencing authority. In this regard, the district court was “deeply” concerned

that, in its own estimation, the judges of the Tenth Circuit might not be “paying

attention to their obligations in reviewing the decisions of Judges of the District

Court.” R., Vol. III, at 12. 

However, we have our responsibilities firmly in hand with respect to trial

judges’ applications of § 3553(a)’s factors. And, regrettably, the district court’s

efforts to assist us caused it to import those sentencing factors into a foreign

sphere—the entry-of-guilty-plea context—and that was legal error. 

 Indeed, the court’s tender of succor is fundamentally off-base because it

would have the effect of hobbling a tool that we have explicitly acknowledged

yields manifold benefits—appellate waivers. In this regard, we have said:

[P]ublic policy strongly supports plea agreements that include an

appeal waiver. A waiver of appellate rights can be of great value

to an accused as a means of gaining concessions from the

government. Appeal waivers also benefit the government by

saving [it] the time and money involved in arguing appeals. 

Society benefits from the finality that waivers bring.

United States v. Elliott, 264 F.3d 1171, 1174 (10th Cir. 2001) (first alteration in

original) (omission omitted) (citations omitted) (quoting United States v.

Michelsen, 141 F.3d 867, 873 (8th Cir. 1998); United States v. Littlefield, 105

F.3d 527, 530 (9th Cir. 1997) (Hall, J., concurring)) (internal quotation marks

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omitted). In applying its misguided § 3553(a) approach, the district court deemed

these general benefits of appellate waivers “irrelevant.” R., Vol. I, at 45. 

Nothing could be further from the truth. 

 In sum, the district court committed legal error in attempting to interject

§ 3553(a)’s sentencing factors into the calculus regarding whether to accept or

reject the appellate waiver in Mr. Vanderwerff’s first plea agreement. 

Consequently, in this respect, the district court abused its discretion.

4

Lastly, though our prior rulings in Parts II.B.1–.3, supra, are sufficient to

support our decision to reverse the district court’s judgment and sentence, we

observe that the district court’s negative frame of mind toward the pleabargaining process seems to have detrimentally influenced its decision to reject

the appellate waiver in Mr. Vanderwerff’s first plea agreement. However, in our

view, the district court lacked any legal basis for setting its face against plea

bargaining. Contrary to the court’s suggestion, plea bargaining is not “of dubious

legality” because it (purportedly) “sacrific[es] constitutional rights on the altar of

efficiency.” R., Vol. I, at 43. True, the district court stated that its skepticism

concerning plea bargaining would not be “determinative” of its ruling on Mr.

Vanderwerff’s first plea agreement, id., Vol. III, at 11, but its patent expression of

invective toward the institution of plea bargaining strongly suggests that the

court’s negative feeling about the institution was a factor (even if not a

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dispositive one) in its decision to reject the agreement at issue containing the

appellate waiver. Tellingly, the district court announced that it would be

inspecting the agreement under “close scrutiny” due to its apparent antipathy

toward plea bargaining as a whole. Id., Vol. I, at 43.

By now it is blackletter law, however, that plea bargaining is strongly

favored. See, e.g., Blackledge v. Allison, 431 U.S. 63, 71 (1977) (“Whatever

might be the situation in an ideal world, the fact is that the guilty plea and the

often concomitant plea bargain are important components of this country’s

criminal justice system. Properly administered, they can benefit all concerned.”);

Santobello v. New York, 404 U.S. 257, 260–61 (1971) (calling plea bargaining “an

essential component of the administration of justice” and “highly desirable . . . for

many reasons”). Indeed, though as noted in Part II.B.1, supra, the district court

erred in concluding that Lafler had anything to say about district courts’ proper

role in the plea-bargaining process, it is noteworthy that a major premise of Lafler

and the Court’s related decision, Frye, was the idea that plea bargaining is

“central to the administration of the criminal justice system.” Frye, 132 S. Ct. at

1407; see Lafler, 132 S. Ct. at 1388 (rejecting the petitioner’s argument that “[a]

fair trial wipes clean any deficient performance by defense counsel during plea

bargaining” because “[t]hat position ignores the reality that criminal justice today

is for the most part a system of pleas, not a system of trials”). 

Moreover, for many reasons, appellate waivers in plea agreements are

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particularly favored. See Elliott, 264 F.3d at 1174 (“[P]ublic policy strongly

supports plea agreements that include an appeal waiver.” (alteration in original)

(quoting Littlefield, 105 F.3d at 530 (Hall, J., concurring)) (internal quotation

marks omitted)); see also United States v. Hahn, 359 F.3d 1315, 1318 (10th Cir.

2004) (en banc) (per curiam) (“[W]e generally enforce plea agreements and their

concomitant waivers of appellate rights.”).5

 Simply stated, the district court’s

personal policy preferences on the plea-bargaining issue—or, indeed, our

own—are irrelevant. Binding precedent has firmly established the legality of plea

bargaining and appellate waivers in plea agreements. The district court was not

empowered to tilt the balance against Mr. Vanderwerff’s first plea agreement

containing an appellate waiver because of its negative views toward plea

bargaining. 

The district court’s decision is particularly troubling because Mr.

Vanderwerff’s plea agreement involved a charge bargain, where the zone of

judicial discretion is ordinarily quite limited. See Robertson, 45 F.3d at 1437–38. 

Notwithstanding the district court’s laments that charge bargains “shunt[ ] to the

5 In this regard, several panels of our court have clearly indicated as

much in persuasive nonprecedential decisions. See United States v. Hill, 568 F.

App’x 549, 554 (10th Cir. 2014) (“We have emphasized the importance of

preserving the benefit of the government’s bargain by enforcing appellate

waivers.” (internal quotation marks omitted)); United States v. Roberts, 189 F.

App’x 761, 763 (10th Cir. 2006) (per curiam) (“Concerns of fairness, integrity,

and public reputation favor enforcing the appellate waiver.”); United States v.

Silva, 189 F. App’x 698, 702 (10th Cir. 2006) (per curiam) (same). 

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margins” its “act of judging,” R., Vol. I, at 42, the law expressly contemplates

that charge bargaining is a province primarily for the exercise of

prosecutorial—not judicial—discretion. See Robertson, 45 F.3d at 1438.6

 

The effect of the district court’s decision to reject Mr. Vanderwerff’s first

plea agreement because it contained an appellate waiver was inconsistent with the

charge-bargain nature of the plea agreement. By relying on legally erroneous and

irrelevant considerations to reject the agreement—most notably, § 3553(a)’s

sentencing factors—the court effectively crippled, and failed to accord proper

deference to, the government’s exercise of prosecutorial discretion in fashioning a

6 Indeed, more generally, the district court’s complaints regarding its

lack of involvement in the plea-bargaining process are at odds with the framework

of plea bargaining established by the federal rules, which discourage active

judicial participation in that process. See Fed. R. Crim. P. 11(c)(1) (“The court

must not participate in [plea-bargaining] discussions.”); United States v. CanoVarela, 497 F.3d 1122, 1132 (10th Cir. 2007) (“Rule 11 ‘is designed to totally

eliminate judicial pressure from the plea bargaining process.’” (quoting United

States v. Casallas, 59 F.3d 1173, 1178 (11th Cir. 1995)) (internal quotation marks

omitted)). Plea bargains are negotiated agreements between prosecutors and

defendants, “just like other bargained-for exchanges.” Littlefield, 105 F.3d at 530

(Hall, J., concurring). We have found that excluding the trial judge from the

bargaining process “minimizes the risk that the defendant will be judicially

coerced into pleading guilty, . . . preserves the impartiality of the court, and . . .

avoids any appearance of impropriety.” Cano-Varela, 497 F.3d at 1132 (quoting

United States v. Kraus, 137 F.3d 447, 452 (7th Cir. 1998)) (internal quotation

marks omitted). Though the district court bemoaned the “push . . . to relegate

[trial judges] to approving or disapproving proposed plea bargains and . . .

determining an appropriate sentence,” R., Vol. I, at 42, it is beyond peradventure

that these acts are of great importance to individual defendants and the proper

administration of the criminal justice system. And the district court has not

demonstrated that the law actually contemplates a different or broader role for the

trial court in this process. 

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charge bargain. For example, the court flatly rejected the government’s argument

that Mr. Vanderwerff’s appellate waiver evidenced his acceptance of

responsibility and remorse—which, significantly, the government made under the

rubric of § 3553(a) as the court required—because it “ignore[d] the nature of Mr.

Vanderwerff’s bargain,” especially overlooking the significant benefit he was

receiving “[i]n exchange for” the waiver. R., Vol. I, at 46. Likewise, the court

found unpersuasive the parties’ argument (again under the court-mandated

framework) that “the dismissal of charges 1 and 3 w[ould] result in a statutory

sentencing range that better accommodates the interests of justice and the

strictures of 18 U.S.C. § 3553.” Id. Specifically, reimagining a linkage between

the § 3553(a) factors and the propriety of the appellate waiver, the court opined:

“[T]he parties seek to limit Mr. Vanderwerff’s sentence to a range of five to ten

years of incarceration. Although these sentencing consequences may have

induced Mr. Vanderwerff to accept the government’s plea bargain, they do not

justify including an appellate waiver.” Id. (emphasis added). Following the

court’s rejection of the plea agreement containing the appellate waiver, the

government apparently decided under its court-constricted scope of discretion that

it only was appropriate to offer Mr. Vanderwerff a different charge bargain that

was considerably less favorable to him—involving a five-year mandatory

minimum and a twenty-year maximum. Thus, the district court’s

decision—predicated on legally erroneous and irrelevant factors—to reject Mr.

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Vanderwerff’s first plea agreement because it contained an appellate waiver is

particularly problematic due to its conflict with the settled law of plea bargaining,

under which courts accord considerable discretion to the government in crafting

charge bargains. 

In sum, far from being (as the district court would have it) a tool of

“dubious legality,” id. at 43, plea bargaining has been consistently endorsed by

the courts and recognized as serving a critical role in the administration of our

criminal justice system. Insofar as the district court rested to any appreciable

degree its decision to reject Mr. Vanderwerff’s first plea agreement containing an

appellate waiver on its negative views toward plea bargaining, the court

committed legal error and thereby abused its discretion. 

C

We have concluded that the district court’s principal bases for rejecting the

appellate waiver in Mr. Vanderwerff’s first plea agreement—and, consequently,

the agreement itself—were legally erroneous and involved irrelevant

considerations. It follows ineluctably that, in effecting the rejection, the district

court abused its discretion. We recognize that when conducting abuse-ofdiscretion analysis, we have on occasion engaged in harmless-error

analysis—either at the request of a party or, “in an appropriate case,” sua sponte.

United States v. Samaniego, 187 F.3d 1222, 1224 (10th Cir. 1999) (quoting

United States v. Torrez-Ortega, 184 F.3d 1128, 1136 (10th Cir. 1999)) (internal

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quotation marks omitted). We decline to engage in such an analysis here. 

Neither party has asked us to examine whether the error was harmless, and both

parties, as well as amicus counsel, urge us to reverse the decision and remand the

case. Under these circumstances, this case is not within the ambit of cases

appropriate for sua sponte harmless-error review. Accordingly, we reverse the

district court’s judgment and sentence. 

III

For the foregoing reasons, we REVERSE and REMAND this case with

instructions to the district court to VACATE its judgment, to permit Mr.

Vanderwerff to withdraw his guilty plea, and to conduct any necessary further

proceedings not inconsistent with this opinion.

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1 

13-1227 – United States v. Vanderwerff

HARTZ, Circuit Judge, concurring: 

 The district court’s critique of plea bargaining would give pause to any thoughtful 

person. But I agree with the opinion of Judge Holmes that the district court committed 

legal error in its opposition to appellate waivers. I write separately to focus on one error, 

the assessment that the earlier judicial approval of such waivers has been undermined by 

the transformation of the Sentencing Guidelines from mandatory to advisory under 

United States v. Booker, 543 U.S. 220 (2005), which was accompanied by the adoption of 

abuse-of-discretion review. 

Booker has not led to a sea change in appellate review of district-court sentencing. 

About the only ways in which appellate review has become more stringent since that 

decision is that we now review (1) whether the district court adequately explained why it 

imposed a sentence outside the guidelines range and (2) whether the sentence was 

substantively reasonable. Yet reversal on the first ground is unusual and easily cured; 

and, at least in this circuit, reversal on the second ground is even rarer. Eliminating the 

possibility of such reversal through an appellate waiver is hardly sufficiently significant 

to require judicial re-examination of appellate waivers. Moreover, apparently most 

appellate waivers are like the one in this case in that they do not apply to challenges to 

sentences outside the guidelines range and therefore do not restrict the new avenues of 

review. 

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