FILED

U.S. COURT OF APPEALS

ELEVENTH CIRCUIT

JANUARY 21, 2005

THOMAS K. KAHN

CLERK

 Honorable Richard Mills, United States District Judge for the Central District of *

Illinois, sitting by designation.

[PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

________________________

No. 04-10874

________________________

D. C. Docket No. 02-60049-CR-DTKH

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

versus 

ANGELA ANN RUBBO, 

a.k.a. Angie, 

Defendant-Appellant. 

________________________

Appeal from the United States District Court

for the Southern District of Florida

_________________________

(January 21, 2005)

Before CARNES and COX, Circuit Judges, and MILLS , District Judge. *
2

CARNES, Circuit Judge:

This Court has previously upheld the enforceability of appeal waivers that

are knowingly and voluntarily entered. E.g., United States v. Bushert, 997 F.2d

1343 (11th Cir. 1993). We have explained how they serve important interests of

the defendant as well as the government, United States v. Buchanan, 131 F.3d

1005, 1008 (11th Cir. 1997), and we could have added the judicial system itself to

the list of beneficiaries. We have also held that “[a] waiver of the right to appeal

includes a waiver of the right to appeal difficult or debatable legal issues—indeed,

it includes a waiver of the right to appeal blatant error.” United States v. Howle,

166 F.3d 1166, 1169 (11th Cir. 1999) (footnote omitted).

Angela Rubbo does not dispute any of that, but she does contend that the

appeal waiver she agreed to as part of her plea bargain ought not prevent her from

raising sentencing issues arising under the Supreme Court’s recent decision in

United States v. Booker, 543 U.S. ___, ___ S.Ct. ___ , 2005 WL 50108 (2005). 

Her argument centers around the “maximum permitted by statute” exception in the

waiver she entered. It is an interesting argument, but ultimately not a persuasive

one. 

A sixty-three count indictment charged Rubbo with mail fraud, wire fraud,

money laundering, and various conspiracies, stemming from a multi-million dollar
3

telemarketing fraud operation that she and her three sons ran. Through plea

negotiations with prosecutors, Rubbo’s attorney managed to whittle the charges

down to one: conspiracy to commit mail and wire fraud in violation of 18 U.S.C. §

371. In return for the government agreeing to dismiss the remaining sixty-two

counts against her and for other favors at sentencing, Rubbo agreed to plead guilty,

cooperate, and waive her right to appeal any sentence she received subject to a few

exceptions. After two hearings, the district court granted Rubbo’s motion to

change her plea to guilty, accepted that new plea, and adjudicated Rubbo guilty of

the one count of violating § 371. 

During the course of one of those hearings, the district court engaged in a

colloquy with Rubbo in which it ensured that she fully understood the appeal

waiver part of her plea agreement and voluntarily consented to it. To the extent

that Rubbo contends that she did not knowingly and voluntarily agree to the appeal

waiver, we reject that contention because it is inconsistent with the record.

At sentencing, the district court imposed over Rubbo’s objections two

enhancements. One was a two-level enhancement either because the offense

involved relocating a fraudulent scheme to another jurisdiction to elude law

enforcement, U.S.S.G. § 2F1.1(b)(5)(A) (Nov. 1998), or because it used 

sophisticated means, U.S.S.G. § 2F1.1(b)(5)(C) (Nov. 1998). The other was a two-
4

level enhancement for being an organizer or leader of a criminal activity that

involved five or more participants or was otherwise extensive, pursuant to U.S.S.G.

§ 3B1.1(c) (Nov. 1998). The district court ultimately sentenced Rubbo to fortyeight months’ imprisonment, twelve short of the statutory cap of sixty months for

the crime. See 18 U.S.C. § 371.

Notwithstanding her promise that she would not appeal, Rubbo did. She

filed a brief contending that the impositions of the enhancements were erroneous

applications of the guidelines. The government responded with a motion to

dismiss Rubbo’s appeal based upon the waiver. See generally Buchanan, 131 F.3d

at 1008–09 (dismissal of appeal based upon waiver should, if possible, occur on

motion before the government’s brief is filed).

Rubbo filed a reply to the government’s dismissal motion in which she

indicated that in light of the intervening decision in Blakely v. Washington, 542

U.S. ___, 124 S. Ct. 2531 (2004), she wanted to raise on appeal the issue of

whether the judge-imposed enhancements she had attacked in her initial brief,

which coincidentally had been filed on the very day that Blakely was released,

were unconstitutionally imposed in violation of the Sixth Amendment. Rubbo

argued that issue was outside the scope of her appeal waiver because, if she were

right on the merits of it, the sentence imposed on her exceeded the “statutory
 Because Rubbo did not raise the Blakely issue in her opening brief, the government 1

contends that she is procedurally barred from arguing it. See United States v. Levy, 379 F.3d

1241, 1242–45 (11th Cir.) (Blakely-type claim waived by failure to raise it in initial brief on

appeal), reh’g denied 391 F.3d 1327 (en banc) (2004); see also United States v. Njau, 386 F.3d

1039, 1042 (11th Cir. 2004) (same). Rubbo urges us not to apply the usual rule because she told

the government in her response to its motion to dismiss that she was going to raise the Blakely

issue and thereby gave the government an opportunity to brief the issue in its own opening brief. 

We need not address that novel procedural argument because Rubbo’s appeal is due to be

dismissed as a result of the appeal waiver irrespective of any procedural bar. 

5

maximum” as defined in Blakely and her waiver explicitly excepted sentences in

excess of the statutory maximum.1

The appeal waiver paragraph in the plea agreement that Rubbo signed says

this: 

The defendant is aware that Title 18, United States Code,

Section 3742 affords the defendant the right to appeal the

sentence imposed in this case. Acknowledging this, in

exchange for the undertakings made by the United States

in this plea agreement, the defendant hereby waives all

rights conferred by Title 18, United States Code, Section

3742 to appeal any sentence imposed, including any

restitution order, or to appeal the manner in which the

sentence was imposed, unless the sentence exceeds the

maximum permitted by statute or is the result of an

upward departure from the guideline range the Court

establishes at sentencing. The defendant further

understands that nothing in this plea agreement shall

affect the government’s right and/or duty to appeal as set

forth in 18 U.S.C. § 3742(b). However, if the United

States appeals the defendant’s sentence pursuant to

Section 3742(b), the defendant shall be released from the

waiver of appellate rights. The defendant understands

that, although the defendant will be sentenced in

conformity with the Sentencing Guidelines, by this

agreement the defendant waives the right to appeal the
6

sentence on the basis that the sentence is the result of an

incorrect application of the Sentencing Guidelines.

The general waiver language—“all rights conferred by Title 18, United States

Code, Section 3742 to appeal any sentence imposed, including any restitution

order, or to appeal the manner in which the sentence was imposed”—certainly is

broad enough to cover any issues arising from Apprendi v. New Jersey, 530 U.S.

466, 120 S. Ct. 2348 (2000), and its progeny, up to and including Booker. Rubbo

has not contended to the contrary. Her point is that there is an exception to that

broad waiver. We have emphasized in the block quote the language setting out

that exception, which is the linchpin to Rubbo’s contention that her appeal waiver

does not apply. 

Rubbo’s position is not outlandish. The plea agreement language permitting

her to escape the waiver if “the sentence exceeds the maximum permitted by

statute” is semantically similar to the “statutory maximum” term that was a key

component of the Supreme Court’s reasoning and analysis in Blakely. In its

opinion in that case, the Court gave this definition of that term: “Our precedents

make clear, however, that the ‘statutory maximum’ for Apprendi purposes is the

maximum sentence a judge may impose solely on the basis of the facts reflected in

the jury verdict or admitted by the defendant.” Blakely, 124 S. Ct. at 2537

(emphasis omitted). Two days before we heard oral argument in this case, the
7

Supreme Court released its Booker decision, and the Blakely issue discussed in

Rubbo’s opposition to the motion to dismiss this appeal became a Booker issue. 

The Supreme Court in Booker quoted the “statutory maximum” definition from its

Blakely opinion. See Booker, 2005 WL 50108, at *7.

Because the sentence the district court imposed on Rubbo goes beyond that

permitted on the basis of the facts she admitted during her plea colloquy, Rubbo

contends that it exceeds the statutory maximum sentence for Booker purposes. 

Given that, she says that her sentence “exceeds the maximum permitted by statute”

for purposes of the exception to the appeal waiver contained in her plea agreement. 

The problem with Rubbo’s contention is its invisible premise, which is that

“statutory maximum” for Booker purposes is the same thing as “the maximum

permitted by statute” for purposes of Rubbo’s appeal waiver. The two are not the

same. The context in which the terms are used and the meaning they convey are

different. After all, “[a] word is not a crystal, transparent and unchanged, it is the

skin of a living thought and may vary greatly in color and content according to the

circumstances and the time in which it is used.” Towne v. Eisner, 245 U.S. 418,

425, 38 S. Ct. 158, 159 (1918) (Holmes, J.).

In the Apprendi/Booker line of decisions, the Supreme Court used the term

“statutory maximum” to describe the parameters of the rule announced in those
8

decisions, a rule that had nothing to do with the scope of appeal waivers. Booker,

2005 WL 50108, at *7; Blakely, 124 S. Ct. at 2536–37; Apprendi, 530 U.S. at 487

n.13 & 490, 120 S. Ct. at 2361 n.13 & 2362–63. The term was defined in a

specialized, which is to say a non-natural, sense. It was defined that way not only

for semantic convenience but also in order to justify and explain the holdings the

Court entered in those decisions. Everyone knows that a judge must not impose a

sentence in excess of the maximum that is statutorily specified for the crime. See,

e.g., Bushert, 997 F.2d at 1350 n.18 (describing as “axiomatic” the rule that “a

court of the United States may not impose a penalty for a crime beyond that which

is authorized by statute”). By labeling a sentence that the judge may not impose

under the Apprendi/Booker doctrine as one in excess of the “statutory maximum,”

the Court may have sought to call into play that well-known principle of law. 

Whether it did, however, is not the point for present purposes. The point

here is that the definition of “statutory maximum” the Supreme Court used to

describe and explain its holdings in those cases says nothing about what Rubbo and

the government meant when they used the term “the maximum permitted by

statute” in the appeal waiver. This is not a matter of legal research. It is a question

of the parties’ intent. 
9

Plea bargains, we have recognized, are like contracts and should be

interpreted in accord with what the parties intended. See Howle, 166 F.3d at 1168 

(“A plea agreement is, in essence, a contract between the Government and a

criminal defendant.”); Allen v. Thomas, 161 F.3d 667, 671 (11th Cir. 1997) (“[W]e

have said that the construction of plea agreements is governed generally by the

principles of contract law, as we have adapted it for purposes of criminal law . . .

.”) (internal marks and citation omitted); United States v. Knight, 867 F.2d 1285,

1288 (11th Cir. 1989) (“When [the defendant] accepted the plea offer, her

discussions with [a DEA agent] were no longer with a view to an agreement; the

negotiations had ended and a plea contract was formed.”). There is nothing to

indicate that when these parties used the language “exceeds the maximum

permitted by statute” to describe the sentence from which Rubbo would be

permitted to appeal they intended those words to have anything other than their

usual and ordinary meaning. That meaning describes the upper limit of

punishment that Congress has legislatively specified for violation of a statute; for

example, five years for violation of 18 U.S.C. § 371. 

For purposes of the exception to the appeal waiver, the parties chose to

define the maximum sentence in terms of what is “permitted by statute,” not in

terms of what is permitted by the Apprendi line of decisions that was evolving at
10

the time. We asked counsel for Rubbo at oral argument whether there was

anything in the record to indicate that the parties intended to reserve a right for her

to appeal any Apprendi-type issues. He replied with commendable candor that

there was not, and that if that had been the intent Rubbo would have raised an

Apprendi issue at the sentence proceeding, which she did not.

We take our final point from the D.C. Circuit’s decision last month in United

States v. West, 392 F.3d 450 (D.C. Cir. 2004), which addressed the question of

whether an exception to a waiver allowing a defendant to appeal if “the Court

sentences [him] to a period of imprisonment longer than the statutory maximum”

permitted an appeal on Apprendi/Blakely grounds. The defendant in that case also

relied upon the definition of “statutory maximum” contained in the Blakely

opinion, but the Court rejected as implausible the idea that the parties could have

intended that meaning. Id. The Court added that giving such an interpretation to

the term “statutory maximum” would also be inconsistent with other provisions of

the plea agreement, thereby violating a cardinal principle of contract interpretation

that a writing is to be interpreted as a whole. Id. (citing Restatement (Second) of

Contracts § 202(2) (1981)). It would be inconsistent, because other provisions of

the plea agreement set out the statutory maximum punishments the defendant could
11

receive for the two charges and, of course, they did so in terms of the punishment

permitted under the terms of the statutes themselves. Id. 

The same is true in the present case. A provision in the plea agreement

states that Rubbo understands and acknowledges that “the Court may impose a

statutory maximum term of imprisonment of up to five (5) years, followed by a

term of supervised release of up to three (3) years, and a fine of up to $250,000,”

and order the defendant to pay restitution. In that provision, “statutory maximum”

unquestionably means the maximum permitted by the statute itself, undiminished

by any Apprendi/Booker considerations. If we were to read the language in the

appeal waiver provision in this same agreement to mean anything else, we would

be interpreting materially identical terms in the same contract to mean substantially

different things. That we will not do. 

In summary, the right to appeal a sentence based on Apprendi/Booker

grounds can be waived in a plea agreement. Broad waiver language covers those

grounds of appeal. Absent some indication that the parties intended otherwise,

when an exception to an appeal waiver is stated in terms of a sentence imposed in

excess of the statutory maximum, those terms should be given their ordinary and

natural meaning. Ordinarily and naturally, “statutory maximum” and “the

maximum permitted by statute” refer to the longest sentence that the statute which
12

punishes a crime permits a court to impose, regardless of whether the actual

sentence must be shortened in a particular case because of the principles involved 

in the Apprendi/Booker line of decisions. 

The government’s motion to dismiss this appeal on the basis of the appeal

waiver is granted. APPEAL DISMISSED.