# U nit edStates C ou rt o f App eal s For th e Firs t C ircu it

No. 05-1566 UNITED STATES OF AMERICA, Appellee,

v . OMAR PARRILLA ROMÁN, Defendant, Appellant.

____________ No. 05-1863 UNITED STATED OF AMERICA, Appellee,

v. CARLOS JAVIER ORTIZ SANTIAGO, Defendant, Appellant.

APPEALS FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO [Hon. Juan M. Pérez-Giménez, U.S. District Judge]

Before Torruella, Circuit Judge, Selya and Tashima,* Senior Circuit Judges.Ramón García García on brief for appellant Parrilla Román.

Jorge L. Armenteros-Chervoni for appellant Ortiz Santiago. Nelson Pérez-Sosa, Assistant United States Attorney, with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, was on brief, for the United States.

May 9, 2007

__________ *Of the Ninth Circuit, sitting by designation.Originally, the airline listed Ortiz's job title as "ramp 1 agent." He later became a fleet service clerk. The district court and the parties s e e m t o have employed the two titles interchangeably. Because nothing turns on this nomenclative point, we use the latter title. -3-

SELYA, Senior Circuit Judge. These sentenc i n g appeals reverberate with the echo of a question that we thought we had laid to rest in United States v. Reccko, 151 F.3d 29 (1st Cir. 1998). This question involves the application of the two-level enhancement for abuse of a position of trust under the current version of the f e d e ral sentencing guidelines. See USSG §3B1.3 (2006). Concluding, as we do, that the district court erred in its application of this guideline, we vacate the defendants' sentences and remand for resentencing consistent with this opinion. I. BACKGROUND

Because these appeals follow the entry of guilty pleas,
we ta k e the relevant facts from the defendants' change-of-plea colloquies, the uncontested portions of the presentence investigation reports, and the transcripts of their disposi tion hearings. See United States v. Dietz, 950 F.2d 50, 51 (1st Cir. 1991). The tale follows.

In more tranquil times, defendants-appellants Carlos Javier Ortiz Santia g o (Ortiz) and Omar Parrilla Román (Parrilla) worked as fleet service clerks for American Airlines at the Luis Muñoz Marín International Airport in Carolina, Puerto Rico. Fleet 1 service clerks are responsible for loading and unloading cargo onto-4-

and off of passenger a i rcraft, handling mail and freight for shipment by air, and cleaning t h e i n terior areas of passenger aircraft. They also drive airline vehicles, operate machinery, guide aircraft through ground-level arrival and departure maneuvers, and help to de-ice airplanes when required. Judging by the defendants' rates of pay, fleet service clerks earn from $10.00 - $12.50 an hour.

In 2003, the defendants supplemented their workload (and, presumably, their income) by conspiring with othe r s to transport cocaine from Puerto Rico to various destinations on the mainland.
T h e basic scheme, with minor variations from caper to caper, operated as follows. Ortiz would receive a s u itcase containing cocaine, w h ich he would then carry or drive through security checkpoints without inspection. He then ensured that the suitcase was stowed safely aboard a designated departure-bound ai rplane. For his part, Parrilla made sure that his confederates knew that "the bird is in flight"; that is, that a cocaine-laden suitcase had been placed aboard a pre-selected flight. On at least two occasions, he provided coconspirators with a baggage claim ticket, flight information, and the assumed name that had been used for such a suitcase.

In d u e s e a s o n , f e d e r a l a g e n t s u n e a r t h e d t h e p l o t . An indictment followed apace. To make a tedious tale tolerably terse, both Ortiz and Parrilla eventually pleaded guilty to a count that-5-

charged conspiracy to p ossess with intent to distribute five or more kilograms of cocaine, in violation of 21 U.S.C. §§ 841, 846.

The district court sentenced Parrilla on March 11, 2005. The main battle was over the applicability vel non of the positionof-trust enhancement. See USSG §3B1.3. Parrilla argued that, given his duties as a f l e e t s ervice clerk, he had no managerial dis c r e t i on, played no supervisory role, and thus could not be deemed to occupy a position of trust. Parrilla buttressed his argument with a copy of the job description for the fleet service clerk position. The argument was in vain. T h e district court imposed the position-of-trust enhancement, stating: Now, you h a v e submitted a copy of the job description, and that is fine. But let's take it one step prior to the job description. If [Parrilla] did not have a security clearance from the Ports Authority whereby he had to comply with certain conditions to obtain the security clearance, he would not have been able to be emp loyed by American Airlines.

. . . . The facts that your client accepted when he pled guilty include[] the fa ct that once inside the airport, the suitcase was provided to the co-defendant, who insured that the suitcase made it on board . . . .

. . . . . . . But he is there in that position be c a u se he held a position of trust or a secured position within the airport, as authorized by Ports Authority.-6- So if he had not had th a t security clearance, he would not have been in a position to insure that the luggage got on the airplane. And tha t i s why his position of private trust did contribute in some significant way to facilitating the commission of the crime. Otherwise, the suitcases would not have been put on board. Combined with Parrilla's base offense level, other adjustments, and criminal history category (I), the offense level increase yielded a guideline sentencing range (GSR) of 87-108 months. Without the enhancement, the GSR would have been 70-87 months. The court levied an 87-month inc a r cerative term — the bottom of the calculated GSR.

The district court convened Ortiz's disposition hearing on April 28, 2005. The hearing unfolded and concluded in much the same manner. Pertinently, Ortiz argued that, as a mere baggage handler, he had no professional or managerial discretion and could
not b e deemed to occupy a position of trust. The government countered that because he had a security clearance that enabled him to pass unchallenged thr ough security checkpoints and transport drugs through restricted areas of the airport without being stopped, he occupied a position of trust.

The district court accepted the government's logic. It reasoned: [N]ot everybody can qualify for [the fleet

service clerk] position. First o f a ll, they have to go through a security check of the airport. They have to submit background information. They have to submit background-7- records. They have to have a police clearance from the polic e t h at no criminal record is involved, and after going through all that, then the airport personnel provides this indiv i d u a l w i t ha p a s s , w h i c h t h e yh a v e to carry all the time with their photograph, which allows them to go into a secured area.

So in that sense, the Defendant is b e i n ga l l o w e dt o g o i n t o a s e c u r e darea because he holds a position of trust. Otherwise, he wouldn't be going into the secured area. Once . . . he is identified as be i n ga p e r s o n o f t r u s t w i t h i n t h e s e cured area of the airport, then he's able to move in a n dout from the secured area to the other areas of the airport to b r i ng in suitcases without having them inspected, and furthermore, to being a ble to place them in the airplanes . . . . With this predicate in mind, the district court concluded that Ortiz, like Parrilla, should receive a position-of-trust enhancement because his position had contributed significantly to the commission of the offense of conviction.

The court increased Oritz's offense level accordingly. Combined with his base offense level, o t h er adjustments, and criminal history category (I), this increase yielded a GSR of 87- 108 months. Without the enhancement, the GSR would have been 70-87 months. The court sentenced Ortiz to serve a low-end 87-month incarcerative term and to pay a $5,000 fine.

Both Parrilla and Ortiz appealed their sentences. This court consolidated the two appeals.-8-

II. DISCUSSION

Th e p r i n c i p a l i s s u e o n a p p e a l i s t h e d e f e n d a n t s ' c laim that the district court erred in imposing the position-of-trust enhancements. Ortiz also attempts to raise a further claim that the district court abused its discretion in failing to reconsider the imposition of the fine. We consider these claims sequentially.

Our standard of review is fam i l i ar. Following the Supreme Court's decision in United States v. Booker, 543 U.S. 220, 245 (20 0 5 ) , which rendered the federal sentencing guidelines advisory, the guidelines remain the starting point for sentencing determinations. See United States v. Gobbi , 4 7 1 F.3d 302, 313 & n.7 (1st Cir. 2006); United States v. Jiménez-Beltre, 440 F.3d 514, 518-19 (1st Cir. 20 0 6 ) (en banc), cert. denied, 127 S. Ct. 928 (2007). This means that, as a first step in the sentencing pavane, the district court must calculate a defendant's GSR. In the typical case, the correct n e s s of that calculation is a necessary precondition to a reasonable sentence. See, e.g., United States v. Robinson, 433 F.3d 31, 35 (1st Cir. 2005).

In reviewing such a calculation, we accept the sentencing court' s findings of fact unless they are clearly erroneous. See United States v. Dixon, 4 4 9 F . 3 d194, 200 (1st Cir. 2006). We review de novo, however, the court's interpretation and application of the guidelines. See United States v. Pho, 433 F.3d 53, 60 (1st Cir. 2006).-9- A. Position of Trust. The guideline at issue here provides: If the d e f endant abused a position of public or private trust . . . in a manner that significantly facilitated the commission or concealment of the offense, increase [the defendant's offense level] by 2 levels. USSG §3B1.3. An application note elaborates:

'Public or private trust' refers to a position of public or private trust characterized by professional or managerial discretion (i.e., substantial discretionary judgment that is ordinarily given considerable deference). Persons holding such positions ordinarily are subject to significantly less supervision than employees whose responsibilities are primarily non-discretionary in nature. For this adjustment to apply, the position of public or private trust must have contributed in some significant way to facilitating the commission or concealment of the offense (e.g., by making the detection of the offense or the defendant's responsibility for the offense more difficult). This adjustment, for example, applies in the case of an embezzlement of a client's funds by an attorney serving as a guardian, a bank executive's fraudulent loan scheme, or the criminal sexual a buse of a patient by a physician under the guise of an examination. This adjustment does not apply in the case of an embez z l e ment or theft by an ordinary bank teller or hotel clerk because such positions are not characterized by the above-described factors. Id., cmt. n.1.

Consistent with this guideline and the quoted application note, we have constructed, and directed sentencing courts to use, a two-step proces s f o r determining whether a position-of-trust-10-

enhancement should be i mposed. The sentencing court must first answer the status question: Did the defendant occupy a position of trust? If not, the inquiry ends. If, however, the status question
pro d u c e s an affirmative response, the court must then answer the conduct question: Did the defendant use that position to facilitate significantly the commission or concealment of t h e o ffense? See Reccko, 151 F.3d at 31; United States v. Gill, 99 F.3d 484, 489 (1st Cir. 1996); United States v. Santiago-Gonzalez, 66 F.3d 3, 8 (1st Cir. 1995). The two steps are separate. As we explained in Reccko, 151 F.3d at 32, care must be taken not to conflate them.

In imposing a position-of-trust enhancement pursuant to section 3B1.3, the Reccko district court inc orrectly determined that the d e f e n dant, a switchboard operator at a municipal police headquarters, held a position o f t r u st precisely because her job provided her with the access needed to commit the charged crime (unlawfully tipping off a suspect to an impending raid). See id. The sentencing court's determination here suffers from much the same infirmity. Rather than first posing the status question — asking whether the fleet service clerk position was characterized by professional or managerial discretion and minimal supervision — the court jumped immediately to the conduct question, zeroing in on the defendants' r e a d y access to restricted areas of the airport. The court then used that access as the basis for a blanket answer-11-

to both the status and the conduct questions. That analysis merged the two distinct steps that Reccko requires.

Recognizing the inconsistency between the district court's approach and the Reccko paradigm, the government tries to distinguish Reccko on the ground that there was no evidence in that case to suggest that the defend a n t h ad obtained a security clearance. To support the relevance of this suggested distinction, the government cites United States v. Castagnet, 936 F.2d 57 (2d Cir. 1991), for the proposition that "[t]he primary trait that distinguishes a person in a position of trust from one who is not is the extent to which the position provides the freedom to commit a difficult-to-detect wrong." Id. at 61-62 (citation and internal quotation marks omitted). Castagnet is inapposite: that decision dealt with a now-obsolete version of section 3B1.3 that antedated the Sentencing Commission's clear focus on professional or managerial discretion and minimal supervision. See Reccko, 151 F.3d at 33. Without more, the security clearance awarded to Ortiz and Parrilla cannot transmogrify a menial position into a position of trust. Cf. United States v. Edwards, 325 F.3d 1184, 1187 (10th Cir. 2003) (rejecting position-of-trust enhancement for clerical position where government alleged "virtual exclusive control" over customer accounts).

Relatedly, the government indulges in an unabashed attempt at bootstrapping. It says that since the defendants were-12-

successful for a time i n smuggling contraband into the airport, their positions must have entailed minimal supervision. That turns the guideline on its head: it does not follow that, merely because a d e f endant's position enables him to commit an offense, the
po s i t i o n must have been unsupervised and, thus, a position of
trust. Cf. id. (explaining that "[o]pportunity and access" do not equate with substantial discretionary judgment); United States v. Sierra, 188 F.3d 798, 802 (7th Cir. 1999) (explaining that the ultimate success of the criminal enterprise is not an independent measure of significant facilitation).

The government's c i tation to our decision in United States v. Casas, 356 F.3d 104 (1st Cir. 2004), is equally unhelpful. While the district court in that case imposed a myriad of upward adjustments, including a position-of-trust enhancement, on a defendant who worked as a baggage handler for American Airlines, the status question was not an issue on appeal. Rather, insofar as the position-of-trust enhancement was concerne d, the panel dealt o n l y with an Apprendi challenge. See id. at 128 (discussing Apprendi v. New Jersey, 530 U.S. 466 (2000)). We werenot asked to decide, nor did we decide, whether the position-oftrust enhancement comported with the guideline.

There is no need to tarry. At bottom, the government's arguments vividly illustrate its lack of comprehens i o n of (or, perhaps, its stubborn unwillingness to accept) the standard that we-13-

delineated in Reccko. T hat is particularly unfortunate here because the facts, as developed in the district court, will not support a finding that the fl e e t service clerk positions are positions of trust within the meaning of USSG §3B1.3. After all, the government concedes that neither Ortiz nor Parrilla wasafforded discretion to establish policies or to supervise coworkers. Moreover, nothing in the record suggests that either of the two men toiled under minimal supervision. To the contrary, the kinds of tasks typically required of fleet servic e c l e rks (e.g., loading and unloading cargo, cleaning cabin interiors, and guiding taxiing aircraft) a r e the kinds of tasks that almost invariably require oversight.

In all events, the government bears the burden of proving the applicability of the position-of-trust enhancement. See United States v. Connell, 960 F.2d 191, 197 (1st Cir. 1992). It suffices to say that the government has not carried that burden here. The fleet service clerk position appears to be on par with the switchboard operator position described in Reccko and with the bank teller and hotel clerk positions identified by the Sentencing Commission as non-trust positions. See USSG §3B1.3, cmt. n.1; see also Unite d S t a t e s v. West, 56 F.3d 216, 220 (D.C. Cir. 1995) (courier). Because neither of the defendants held a position of public or private trust, the district court erred in enhancing their offense levels under section 3B1.3.-14- B. The Fine.
A s a postscript of sorts, we briefly address Ortiz's objection to the $5,000 fine imposed by the district court (an objection that he couches in the form of an objection to the denial of his serial mo t i o n s t o reconsider the fine). As we explain below, he has waived his right to appeal that impost.

Ortiz pleaded guilty pursuant t o a negotiated plea agreement with the government (the Agreement). The Agreement included an explicit commitment that as long as the district court accepted t he Agreement and sentenced him in accordance with its terms, he "waive[d] a n d surrender[ed] his right to appeal the judgment and sentence in this case." The district court accepted the Agreement and, in doing so, received appropriate assurances that this waiver was knowing and voluntary. The court proceeded to sentence Ortiz within the parameters of the Agreement.

In his appellate brief, Ortiz does not mention this waiver. It is easy to see why: the waiver was u n e q u i v ocal. The only reservat i o n of a right to appeal concerned the possible application of the hotly contested position-of-trust enhancement. See supra Part II(A).

We consistently have upheld properly phrased waivers of the right to appeal from criminal sentencing decisions. See, e.g., United States v. Miliano, 480 F.3d 605, 608 (1st Cir. 2007); United States v. Gil-Quezada, 445 F.3d 33, 36-37 (1st Cir. 2006); UnitedAl t h o u g hi t m a yb e t a n t a m o u n t t o c a r t i n gc o a l t o N e w c a stle, 2 we note that a sentencing court has wide discretion in deciding whether or not to impose a fine. See United States v. Savoie, 985 F.2d 6 1 2 , 6 2 0 ( 1 s t C i r . 1 9 9 3 )
. T h e p r e s u mp t i o n i s t hat a sentencing court should "impose a fine in all cases, except where the defendant establishes that he is unable to pay and is unlikely to become able to pay any fine." USSG §5E1.2(a). The defendant bears the burden of showi n g that this presumption should not operate in his case. United States v. Peppe, 80 F.3d 19, 22 (1st Cir. 1996). To carry that burden, he must show an inability to pay the fine either presently or in the future. United States v. Rowe, 268 F.3d 34, 38 (1st Cir. 2001). Given Ortiz's work history, a finding of likely future ability to pay a relatively modest fine was well within the sentencing court's discretion. -15- States v. Teeter, 257 F.3d 14, 25-26 (1st Cir. 2001). There is no apparent reason to depart from this praxis today. See Miliano, 480 F.3d at 608 (explaining that where "the defen d a n t simply ignores the waiver [of appeal] and seeks to argue the appeal as if no waiver ever had been executed, he forfeits any right to contend either that the waiver should not be enforced or that it does not apply"). The waiver, then, undercuts Ortiz's a ttempt to appeal from the imposition of the fine. 2

It makes no difference that Ortiz has couched his claim of error in terms of the denial of his serial motions to reconsider
t h e fine. Because Ortiz waived his right to appeal the fine itself, see text supra, we discern no legally cognizable basis on which he can challenge the denial of motions to reconsider its imposition. A criminal defenda n t w h o, like Ortiz, knowingly and volu n t a r i l yw a i v e s h i s r i g h t t o a p p e a l a l l o r s o m e p a r t o f h is sentence, cannot evade the effects of that waiver by the simple-16-

expedient of moving to reconsider the unappealable sentence and then appealing the denial of that motion. Cf. United States v. Joiner, 183 F.3d 635, 645 (7th Cir. 1999) (explaining that waiver of appeal of sentence constitutes an implied waiver of the right to raise an ineffective assistance of counsel claim based on "gardenvariety attacks on his sentence . . . in the gu i s e of a claim of ineffective counsel"). III. CONCLUSION

We need go no further. Because the district court erred in imposing position-of-trust enhancements, we vacate the defendants' sentences and remand for resentencing without resort to those enhancements. The guidelines are, of course, adviso r yin nature, see Booker 543 U.S. at 245, and the district court remains free, after properly calculating the guideline range, to impose reasonable sentences of such duration as it deems fitting. That court, if it so chooses, may also reimpose the disputed fine.

Vacated and remanded.