           Case: 17-12132   Date Filed: 08/30/2018   Page: 1 of 15


                                                      [DO NOT PUBLISH]



             IN THE UNITED STATES COURT OF APPEALS

                     FOR THE ELEVENTH CIRCUIT
                       ________________________

                             No. 17-12132
                         Non-Argument Calendar
                       ________________________

               D.C. Docket No. 8:16-cr-00182-RAL-TGW-1



UNITED STATES OF AMERICA,

                                                      Plaintiff - Appellee,

                                  versus


MICHAEL JOSEPH ARMANO,

                                                      Defendant - Appellant.

                       ________________________

                Appeal from the United States District Court
                    for the Middle District of Florida
                      ________________________

                             (August 30, 2018)



Before JILL PRYOR, HULL and JULIE CARNES, Circuit Judges.

PER CURIAM:
             Case: 17-12132        Date Filed: 08/30/2018   Page: 2 of 15


      Pursuant to a plea agreement, Michael Armano pled guilty to one count of

enticing a minor to engage in a sexual act and one count of possessing child

pornography. The district court accepted Armano’s plea and sentenced him to 360

months of imprisonment on the enticement count and 120 months on the

possession count, to run concurrently, followed by a lifetime term of supervised

release. On appeal, Armano argues that his conviction and sentence should be

overturned for two reasons. First, he argues the government breached the plea

agreement by failing to file a motion to reduce Armano’s sentence based on the

substantial assistance he provided to the government. Second, he argues the plea

agreement is invalid because Armano was unaware that the agreement’s factual

proffer could be used to enhance his sentence. After careful review, we affirm.

                              I.      BACKGROUND

A.    Written Plea Agreement

      A federal grand jury charged Armano with one count of enticement of a

minor to engage in a sexual act, in violation of 18 U.S.C. § 2422(b) (“Count 1”);

one count of enticement of a minor to engage in sexually explicit conduct for the

purpose of producing a visual depiction, in violation of 18 U.S.C. § 2251(a), (e)

(“Count 2”); and one count of possession of child pornography, in violation of 18

U.S.C. § 2252(a)(4)(B), (b)(2) (“Count 3”). Pursuant to a written plea agreement,

Armano pled guilty to Counts 1 and 3. Through the agreement, Armano admitted


                                            2
                  Case: 17-12132         Date Filed: 08/30/2018        Page: 3 of 15


to certain facts, including that he had “targeted at least 60 children online.” Doc.

40 at 24.1

       The agreement included a “Substantial Assistance” provision, which stated

that Armano would cooperate with the government in investigating and

prosecuting other individuals and testify in other proceedings. It provided that “[i]f

the cooperation [was] completed prior to sentencing,” the government would

“consider whether such cooperation qualifie[d] as ‘substantial assistance’ in

accordance with the policy of the United States Attorney for the Middle District of

Florida, warranting the filing of a motion . . . pursuant to [United States Sentencing

Guidelines] § 5K1.1[] or . . . 18 U.S.C. § 3553(e).” Id. at 6-7.2 The agreement

made clear that “the determination as to whether ‘substantial assistance’ has been

provided” and whether the government would file a corresponding motion “rests

solely with [the government].” Id. at 7.

       The agreement also set forth the penalties applicable to Armano’s offenses.

It stated that Armano faced a statutory maximum penalty of life in prison on the

child enticement count and a statutory maximum penalty of 10 years in prison on


       1
           Citations to “Doc. #” refer to the district court docket in this case.
       2
          Section 5K1.1 of the Sentencing Guidelines allows the district court to sentence a
defendant who has provided substantial assistance below the minimum sentence required by the
guidelines. Title 18 Section 3553(e) of the United States Code states that “[u]pon motion of the
Government, the court shall have the authority to impose a sentence below a level established by
statute as a minimum sentence so as to reflect a defendant’s substantial assistance in the
investigation or prosecution of another person who has committed an offense.”
                                                    3
              Case: 17-12132     Date Filed: 08/30/2018   Page: 4 of 15


the possession of child pornography count, and that the court could impose the

statutory maximum. The agreement provided that Armano “expressly waive[d]”

the right to appeal his sentence on any ground. Id. at 21. Through the agreement,

Armano stated that he was pleading guilty freely and voluntarily and without

“threats, force, intimidation, or coercion of any kind.” Id. at 22. He acknowledged

the charged offenses and the applicable penalties and agreed that he was satisfied

with the representation and advice he had received from his attorney.

B.     Plea Hearing

       At the plea hearing, Armano pled guilty to Counts 1 and 3. During the

hearing, the district court placed Armano under oath and confirmed that he had an

opportunity to meet with his attorney and discuss the case with her. Armano

testified that he had a bachelor’s degree, understood English, had never been

treated for a mental illness, and was able to think clearly. He stated that he

understood he was pleading guilty and confirmed that he had signed the written

plea agreement after reviewing “each and every provision” with his attorney. Doc.

70 at 8. He testified that he understood the agreement and did not have questions

about it.

       The district court specifically discussed with Armano the Substantial

Assistance provision to ensure that Armano was “absolutely clear on what the

government is agreeing to do.” Id. at 11. The district court explained that “[t]he


                                          4
              Case: 17-12132     Date Filed: 08/30/2018     Page: 5 of 15


government is not saying that if you cooperate with them . . . they will in fact . . .

file a motion for a downward departure.” Id. Instead, the district court explained,

the government agreed only that it would “evaluate in good faith whether any

information or assistance you provide them qualifies as substantial assistance.” Id.

at 12. Armano confirmed that he understood. The district court continued:

      If you cooperate with the government and, when we come to
      sentencing . . . the government declines to file [the substantial
      assistance] motion, there’s only one very limited circumstance that
      would allow me to intervene on your behalf and that is if you could
      make a substantial showing to me that the reason they didn’t file the
      motion was based on what we call an unconstitutional motive . . . .
      It’s a very heavy burden and unless you can prove that to me . . . the
      decision whether to file that motion rests with [the government].

Id. Armano again confirmed that he understood. The district court asked the

government if Armano had been cooperating, and the government responded that

he had.

      The district court then sought to confirm that Armano knew he was waiving

his right to appeal his sentence on most grounds, including on the basis of an error

in calculating the sentencing guidelines range. The district court noted that “in

these sex-related cases . . . there are all kinds of upward adjustments under the

Guidelines.” Id. at 15. The district court confirmed with Armano that he had

discussed those adjustments with his attorney and that he knew he was waiving his

right to appeal any determination that he qualified for such an adjustment. Armano

also confirmed that he and his attorney had discussed the guidelines and how they
                                           5
              Case: 17-12132     Date Filed: 08/30/2018      Page: 6 of 15


might affect his case. The district court told Armano that the court’s calculation of

his guidelines range “[would] control” even if it differ[ed] from any estimate his

attorney had provided him, and that he could not withdraw his guilty plea if his

attorney’s estimate turned out to be incorrect. Id. at 22.

      After Armano stated that he wished to plead guilty to Counts 1 and 3, the

district court confirmed that Armano had understood the proceeding, answered all

of the court’s questions completely and truthfully, and did not need to confer with

his attorney any further. The district court found that Armano had pleaded guilty

freely, voluntarily, and intelligently. The court accepted Armano’s plea and

adjudged him guilty.

C.    Sentencing Hearing

      Prior to sentencing, in the Presentence Investigation Report (“PSI”), the

probation officer recommended a guidelines range of life in prison. That

recommendation was based, in part, on the fact that Armano’s plea agreement

included stipulations to targeting at least 60 victims, which resulted in the creation

of numerous “pseudo counts.” See U.S.S.G. § 1B1.2(c) (“A plea agreement . . .

containing a stipulation that specifically establishes the commission of additional

offense(s) shall be treated as if the defendant had been convicted of additional

count(s) charging those offense(s).”). At sentencing, Armano objected to the

proposed guidelines calculations on several grounds, including the creation of


                                           6
              Case: 17-12132      Date Filed: 08/30/2018    Page: 7 of 15


pseudo counts, arguing that the plea agreement’s reference to 60 victims should not

serve as the basis for additional counts. The district court overruled those

objections and adopted the PSI.

      The government recommended a sentence of life in prison. The prosecutor

argued that Armano was “obsessed with sexually exploiting kids” and that he

“[could not] stop himself even if he may want to.” Doc. 67 at 151. The

government argued that Armano was likely to be a recidivist because he “could not

control himself . . . [a] fact that’s impossible to deny.” Id. at 179. The district

court told the prosecutor to “[q]uit the histrionics” and “take it easy.” Id. at 180.

After hearing argument from Armano, the district court varied downward by one

offense level, sentencing Armano to 360 months of imprisonment on Count 1 and

120 months of imprisonment on Count 3, to be served concurrently, followed by a

lifetime term of supervised release. This is Armano’s appeal.

                         II.    STANDARDS OF REVIEW

      This Court ordinarily reviews de novo whether the government has breached

a plea agreement and whether a plea was made voluntarily. United States v. De La

Garza, 516 F.3d 1266, 1269 (11th Cir. 2008) (breach of a plea agreement); United

States v. Bushert, 997 F.2d 1343, 1352 (11th Cir. 1993) (voluntariness of a guilty

plea). If the defendant fails to raise either of these issues before the district court,

however, we review for plain error. De La Garza, 516 F.3d at 1269; United States


                                            7
              Case: 17-12132      Date Filed: 08/30/2018    Page: 8 of 15


v. Moriarty, 429 F.3d 1012, 1018 (11th Cir. 2005). Under plain error review, there

must be (1) an error, (2) that is plain, (3) that affects the defendant’s substantial

rights, and (4) that seriously affects the fairness, integrity, or public reputation of

judicial proceedings. United States v. Olano, 507 U.S. 725, 732 (1993).

                                 III.   DISCUSSION

A.    The Government’s Alleged Breach of the Plea Agreement

      Armano argues that the government breached its agreement by failing to file

a motion for substantial assistance under U.S.S.G. § 5K1.1. Because Armano

failed to make this argument in the district court, we review it for plain error.

When a guilty plea rests “in any significant degree on a promise or agreement of

the prosecutor, so that it can be said to be part of the inducement or consideration,

such promise must be fulfilled.” Santobello v. New York, 404 U.S. 257, 262

(1971). To determine whether the government has breached a plea agreement, “we

must first determine the scope of the government’s promises.” United States v.

Copeland, 381 F.3d 1101, 1105 (11th Cir. 2004).

      The government promised Armano that it would “consider” whether his

assistance qualified as substantial assistance under its policies and whether it

would introduce a motion to that effect. Doc. 40 at 6. The plea agreement

specifically stated that the decision as to whether the government would introduce

a substantial assistance motion to reduce Armano’s sentence “rest[ed] solely with


                                            8
              Case: 17-12132     Date Filed: 08/30/2018    Page: 9 of 15


the [government].” Id. at 7. And as the district court explained to Armano at the

plea hearing, the government agreed only to “evaluate in good faith whether any

information or assistance . . . qualifie[d] as substantial assistance.” Doc. 70 at 12.

Even assuming that Armano fully cooperated with the government, therefore, the

government never agreed to introduce a substantial assistance motion and did not

breach the plea agreement by failing to do so.

      Armano argues that the government breached the plea agreement by failing

to evaluate “in good faith” whether he had provided substantial assistance. He

points to the prosecutor’s statements during sentencing that Armano was

“obsessed” with child pornography and that he could not stop himself from

committing another offense, arguing that these comments show that the

government never intended to offer the substantial assistance motion. We disagree

with Armano that these statements—which were made without reference to

Armano’s assistance—show that the government failed to evaluate his assistance

in good faith. And, in any event, because Armano failed to raise this argument

during sentencing, the district court did not plainly err by failing to consider sua

sponte whether the plea agreement had been breached on that basis. See United

States v. Forney, 9 F.3d 1492, 1500 (11th Cir. 1993) (explaining the defendant’s

“attempt to allege bad faith by the government for not making a [§] 5K1.1 motion




                                           9
               Case: 17-12132   Date Filed: 08/30/2018    Page: 10 of 15


[was] unavailing because he did not raise this objection with the district court at

the sentencing proceeding”).

      Armano further argues that his conviction and sentence should be overturned

because the government was motivated by an unconstitutional factor in declining

to make a substantial assistance motion. Although, in general, introducing a

substantial assistance motion is a matter of prosecutorial discretion, that discretion

“is subject to constitutional limitations that district courts can enforce.” Wade v.

United States, 504 U.S. 181, 185 (1992). A prosecutor may not, for example,

decide against introducing a substantial assistance motion because of factors such

as “the defendant’s race or religion.” Id. at 186. But as the Supreme Court has

explained, a defendant arguing that a prosecutor had an unconstitutional motivation

must make some showing beyond mere “generalized allegations of improper

motive.” Id.

      Armano makes only generalized allegations here. He argues that the

prosecutor’s comments about his obsession with child pornography were improper,

but he does not explain how those comments relate to an unconstitutional

motivation, like his race or his religion. Further, the prosecutor’s statements

suggesting that Armano would commit another offense related to child

pornography pertained to the factors the district court must consider during

sentencing, including the need for the sentence to deter criminal conduct and


                                          10
               Case: 17-12132       Date Filed: 08/30/2018       Page: 11 of 15


protect the public from further crimes. See 18 U.S.C. § 3553(a)(1)-(2). We thus

reject Armano’s argument that the prosecutor’s comments showed that the

government was unconstitutionally motivated in deciding not to introduce a

substantial assistance motion. Because Armano has identified no error with

respect to the government’s decision against introducing a substantial assistance

motion, we need not discuss the remaining prongs of the plain error test. 3

B.     The Knowing and Voluntary Nature of Armano’s Guilty Plea

       Armano argues that his conviction was not knowing or voluntary because he

was unaware that the facts he admitted in the plea agreement could be used to

enhance his sentence. Because Armano failed to make this argument during

sentencing, we review it for plain error. “A guilty plea involves the waiver of a

number of a defendant’s constitutional rights, and must therefore be made

knowingly and voluntarily to satisfy the requirements of due process.” Moriarty,

429 F.3d at 1019. This Court has recognized three “core principles” as necessary

to a knowing and voluntary plea. United States v. Mosley, 173 F.3d 1318, 1322

(11th Cir. 1999) (internal quotation marks omitted). The defendant must (1) enter

his guilty plea free from coercion, (2) understand the nature of the charges, and (3)




       3
         Armano argues that we should review his argument de novo, rather than for plain error,
but because he identifies no error, the standard of review makes no difference to the outcome of
his appeal.
                                               11
             Case: 17-12132    Date Filed: 08/30/2018    Page: 12 of 15


understand the consequences of his plea. Id. The district court addressed each of

these core concerns in accepting Armano’s plea.

      First, the district court ensured that Armano’s plea was not coerced.

Armano testified that he had not been induced by any promises or assurances other

than those contained in the plea agreement, and he stated that no one had made any

claims about the sentence the district court would impose on him. He also

confirmed that he had not been threatened or coerced into pleading guilty. Armano

agreed that he was pleading guilty only “because it’s what [he] want[ed] to do and

for no other reason.” Doc. 70 at 31.

      Second, the district court ensured that Armano understood the nature of the

charges against him. We have held that “there is no one mechanical way” that a

district judge must advise a defendant of the charges to which he is pleading guilty.

Mosley, 173 F.3d at 1322 (internal quotation marks omitted). Instead, we assess

each plea colloquy “individually based on various factors, such as the simplicity or

complexity of the charges and the defendant’s sophistication and intelligence.” Id.

at 1322-23 (internal quotation marks omitted). Here, the district court confirmed

that Armano could read, write, and speak English; that he had a college education;

that he understood the proceeding; and that he was not under the influence of drugs

or any other substance. The district court also listed the elements of each offense

the government would have to prove beyond a reasonable doubt if Armano were to


                                         12
                Case: 17-12132   Date Filed: 08/30/2018   Page: 13 of 15


proceed to trial. Armano testified that he had reviewed the indictment and the plea

agreement, and that he understood the specific factual circumstances underlying

the offenses.

      Third, the district court ensured that Armano understood the consequences

of his plea. “To ensure compliance with this third core concern, [Federal Rule of

Criminal Procedure] 11(b)(1) provides a list of rights and other relevant matters

about which the court is required to inform the defendant prior to accepting a

guilty plea.” Moriarty, 429 F.3d at 1019. Relevant here, the district court must

inform the defendant of any maximum possible penalty and it must ensure the

defendant understands that the district court has an obligation to calculate and

consider the applicable guidelines range, to consider any possible departures under

the guidelines, and to consider the sentencing factors in 18 U.S.C. § 3553(a). Fed.

R. Crim. P. 11(b)(1)(M). Here, the district court informed Armano of the statutory

maximum penalties applicable to Counts 1 and 3. The district court also ensured

that Armano had discussed possible sentencing enhancements with his attorney,

noting that “in these sex-related cases . . . there are all kinds of upward adjustments

under the Guidelines.” Doc. 70 at 15. The district court also told Armano that its

calculation of the guidelines range would “[would] control” even if it were

different than the estimate his attorney had provided him. Id. at 22.




                                          13
               Case: 17-12132       Date Filed: 08/30/2018      Page: 14 of 15


       According to Armano, the district court should have explained to him that

the statement contained in the plea agreement that he had “targeted at least 60

children online” could be used to enhance his sentence. Doc. 40 at 24. But Rule

11 “does not require the court to specify which guidelines will be important or

which grounds for departure might prove to be significant.” United States v.

Bozza, 132 F.3d 659, 661-62 (11th Cir. 1998) (internal quotation marks omitted)

(discussing Rule 11(c)(1)). Instead, where the district court confirms “at the plea

proceeding that [the defendant] knew about the Sentencing Guidelines and that he

had discussed the effect of the Sentencing Guidelines on his sentence with his

attorney,” the plea is knowing and voluntary. Mosley, 173 F.3d at 1328. “With

respect to the Sentencing Guidelines, that is all we require the district judge to do.”

Id. We thus disagree with Armano that the district court should have rejected his

plea because it was unknowing and involuntary. Because Armano has identified

no error related to the district court’s acceptance of his guilty plea, we need not

address the rest of the plain error test.4



       4
         We decline to consider on direct appeal Armano’s argument that his attorney’s
performance was deficient. See United States v. Bender, 290 F.3d 1279, 1284 (11th Cir. 2002)
(“We will not generally consider claims of ineffective assistance of counsel raised on direct
appeal where the district court did not entertain the claim nor develop a factual record.”).
Because there is no factual record pertaining to whether Armano’s attorney was ineffective, that
claim would be better addressed in a 28 U.S.C. § 2255 motion. See United States v. Patterson,
595 F.3d 1324, 1328 (11th Cir. 2010) (“[T]he preferred means for deciding a claim of ineffective
assistance of counsel is through a 28 U.S.C. § 2255 motion even if the record contains some
indication of deficiencies in counsel’s performance.” (internal quotation marks omitted)).
                                              14
      Case: 17-12132    Date Filed: 08/30/2018   Page: 15 of 15


                       IV.   CONCLUSION

For these reasons, we affirm Armano’s conviction and sentence.

AFFIRMED.




                                 15
