                Not for Publication in West's Federal Reporter

          United States Court of Appeals
                       For the First Circuit


No. 04-2246

                             UNITED STATES,

                                Appellee,

                                     v.

                     YIRIS QUIRINDONGO-COLLAZO,

                        Defendant, Appellant.


          APPEAL FROM THE UNITED STATES DISTRICT COURT

                 FOR THE DISTRICT OF PUERTO RICO

        [Hon. Jay A. García-Gregory, U.S. District Judge]


                                  Before

                       Lipez, Circuit Judge,
                 Campbell, Senior Circuit Judge,
                    and Howard, Circuit Judge.


     Ryan Thomas Truskoski on brief for appellant.
     H.S. Garcia, United States Attorney, Nelson Pérez-Sosa,
Assistant United States Attorney and Jacqueline D. Novas, Assistant
United States Attorney on brief for appellee.



                           January 23, 2007
            Per Curiam.     Appellant Yris Quirindongo-Collazo executed

his plea agreement before Blakely v. Washington, 542 U.S. 296

(2004), was decided. He was sentenced after Blakely but before the

United States Supreme Court decided United States v. Booker, 543

U.S. 220 (2005).     While appellant's direct appeal was pending in

this court, the Booker decision was announced. Appellant now seeks

to set aside his sentence pursuant to Booker.

            In his opening brief to this court, appellant failed to

mention that his plea agreement contained an appeal waiver, and he

failed to present any argument for setting aside the waiver.

Rather, after the government filed its motion for summary dismissal

based on the waiver, appellant filed a reply brief in which he

attempted to summarily adopt his co-appellant's1 opening brief

argument regarding his appeal waiver, citing Fed. R. App. P. 28(i).

Appellant's opening brief also argues, irrelevantly, that United

States v. Antonakopolous, 399 F.3d 68 (1st Cir. 2005), is wrongly

decided and that appellant is entitled to de novo or harmless error

review.

            Under   stare    decisis    principles,   this   panel   cannot

overrule Antonakopoulos, nor is there the least reason here to

consider doing so.          Quite apart from Antonakopoulos, however,

appellant is entitled to the harmless error standard he seeks.           As

we stated immediately following the Booker decision, in cases


     1
          United States v. Nisbett-Joseph, Appeal No. 04-1539.

                                       -2-
available to counsel before appellant's opening brief was filed

with this court, harmless error review is applied in cases where

the defendant has properly preserved a claim of Booker error in the

district court.         United States v. Heldeman, 402 F.3d 220, 224 (1st

Cir. 2005); see also United States v. Vazquez-Rivera, 407 F.3d 476,

489 (1st Cir.), cert. denied, 126 S. Ct. 279 (2005).                       The record

here       plainly    shows    that,     at   the    sentencing     hearing,   defense

counsel2 objected to appellant's sentence on Blakely grounds, and

the    district        court       assured     appellant     his    objections     were

"preserved."           In    its    opening    brief,    the   government      properly

identified and argued the harmless error standard of review.

               Before this court can review appellant's sentence under

the harmless error rubric, however, we must determine whether

appellant's pre-Blakely appeal waiver should be enforced.                       Setting

aside the question of whether Rule 28(i) permits an appellant, in

his reply brief, to adopt an argument presented in a co-appellant's

opening brief, as a general rule we have held that "legal argument

made for the first time in an appellant's reply brief comes too

late and need not be addressed."                    United States v. Brennan, 994

F.2d 918, 922 n.7 (1st Cir. 1993).                  Under Massaro v. United States,

538    U.S.    500,    508     (2003),    however,      in   view   of   the   "obvious

deficiencies in representation" in appellate counsel's failure to

mention the appeal waiver or raise the issue of its enforceability


       2
            Different counsel represents appellant in this appeal.

                                              -3-
in appellant's opening brief, we will exercise our discretion to

consider appellant's late-raised argument that his appeal waiver is

unenforceable.

            After careful review of the record and applying the

three-part test described in United States v. Teeter, 257 F.3d 14,

25-26 (1st Cir. 2001), we conclude that the appeal waiver is

unenforceable, although not for the reasons argued by appellant.

As we explained in United States v. Soto-Cruz, 449 F.3d 258, 262

(1st Cir. 2006), the mere fact that Booker was decided after

appellant entered into his appeal waiver does not "somehow ...

render the enforcement of his appeal waiver a miscarriage of

justice."     Where, as here, a defendant has stipulated to the

sentencing facts, agreed to be sentenced pursuant to the then-

mandatory guidelines, and is in fact sentenced as specified in the

plea agreement, the subsequent change in the law announced in

Booker, without more, provides no basis for setting aside the

sentence.    Soto-Cruz, 449 F.3d at 262 (citing United States v.

Griffin, 418 F.3d 881, 882 (8th Cir. 2005) ("The fact that [the

defendant] did not anticipate the Blakely or Booker rulings does

not place the issue outside the scope of the waiver.")).

            In this case, it is clear from the record that Teeter's

first prong has been satisfied. The written plea agreement clearly




                                 -4-
sets forth the terms of the appeal waiver.3               257 F.3d at 24.

Compliance    with    Teeter's   second   prong   is,   however,   far   more

doubtful.    Teeter's second prong requires that the district court,

at the change of plea hearing, "call the waiver to the defendant's

attention and question him closely in order to ensure that he has

a full understanding of the waiver provisions and that he has

voluntarily elected to waive his right of appeal."           United States

v. Gil-Quezada, 445 F.3d 33, 36 (1st Cir. 2006) (citing Teeter, 257

F.3d at 24, and Fed. R. Crim. P. 11(b)(1)(N) (requiring such a

colloquy)).    The transcript of appellant's change of plea hearing

indicates that the magistrate judge asked just one question about

the appeal waiver, as follows:

              THE MAGISTRATE: Very well, also this plea agreement
              contains an important section ... and it reads as
              follows.


              "If the court accepts the terms and conditions within
              this plea agreement, then you will be waiving and
              giving up your right to appeal your judgment of
              conviction and also the sentence imposed by the court",
              do you understand that?

              MR. QUIRINDONGO: Yes.

This is the only mention of the appeal waiver during the change of

plea colloquy.       Moreover, the magistrate judge failed to mention



     3
        "The defendant hereby agrees that if this Honorable Court
accepts this Plea Agreement and sentences him according to its
terms and conditions, defendant waives and surrenders his right to
appeal the judgment and sentence in this case." The plea agreement
contains no exceptions or qualifications to this broad language.

                                    -5-
the appeal waiver in her Report and Recommendation to the district

court.

       At the sentencing hearing, after defense counsel voiced his

Blakely objections, the judge, defense counsel, the government, and

the probation officer had an extensive discussion premised on the

assumption that appellant could and would appeal.                    During this

discussion, there was no mention by any party of the appeal waiver,

nor of any effect that waiver might have on appellant's right to

appeal. The court described the contemplated appeal as appellant's

unqualified "right" and repeatedly stated that the issues were

preserved for appeal so that "[i]f the defendant wishes to raise

them on appeal, he is free to do so."                     At the close of the

sentencing hearing, directly contrary to Teeter's teaching to avoid

"blanket assurance[s] about the right to appeal," 257 F.3d at 25,

the court gave detailed instructions pursuant to Fed. R. Crim. P.

32(c)(5) concerning appellant's appeal rights, including how and

when   to   file    a   notice   of    appeal.      The      statements    made   at

appellant's sentencing hearing went well beyond the kinds of

general assurances we have determined in other cases had no effect

on a knowing and voluntary waiver.               See, e.g., United States v.

Gil-Quezada, 445 F.3d 33, 36-37 (1st Cir. 2006) (judge's general

comments    at     sentencing    had   no     bearing   on    whether     appellant

knowingly and voluntarily waived his appellate rights when he

entered his guilty plea four months earlier); United States v. De-


                                        -6-
La-Cruz Castro, 299 F.3d 5, 12 (1st Cir. 2002) (judge's comment

that appellant could appeal "in some circumstances," viewed in

context, did not contradict waiver).          We thus conclude that this

is one of those isolated and extraordinary situations where an

appeal waiver was and, in the interest of justice, should be held,

ineffective.

      Turning now to the record, we cannot conclude that the Booker

error in appellant's sentencing was harmless beyond a reasonable

doubt.      Vazquez-Rivera, 407 F.3d at 489-90; United States v.

Fornia-Castillo, 408 F.3d 52, 73 (1st Cir. 2005).               "We must be

convinced that a lower sentence would not have been imposed had the

Guidelines been advisory.      This is an extremely difficult, but not

impossible, standard to meet." Vazquez-Rivera, 407 F.3d at 489-90.

That appellant stipulated to the sentencing facts "would not be

sufficient to show beyond a reasonable doubt that the judge, acting

under an advisory Guidelines system, would have applied the same

sentence on the basis of those factors," id., particularly here,

where the stipulated drug quantity attributed to appellant in his

plea agreement exposes him to a mandatory minimum sentence of five

years, 21 U.S.C. § 841(b)(1)(B), and he was sentenced to 121 months

-- the minimum allowed under the then-mandatory guidelines.

      In the very unique circumstances of this case, we therefore

decline to enforce the appeal waiver.        The conviction is affirmed,

but   the   sentence   is   vacated    and   the   case   is   remanded   for


                                      -7-
resentencing.    We intimate no view on whether appellant should

receive   a   higher   or   lower   sentence   on   remand,   or   on   the

reasonableness of his previous sentence or on any revised sentence.




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