Not for Publication in West's Federal Reporter 

United States Court of Appeals

For the First Circuit 

No. 14-1224 

UNITED STATES OF AMERICA, 

Appellee, 

v. 

SERGIO SANTA-OTERO, 

Defendant, Appellant. 

APPEAL FROM THE UNITED STATES DISTRICT COURT 

FOR THE DISTRICT OF PUERTO RICO 

[Hon. José Antonio Fusté, U.S. District Judge] 

Before 

Howard, Chief Judge, 

Torruella and Barron, Circuit Judges. 

Alejandra Bird López on brief for appellant. 

 Tiffany V. Monrose, Assistant United States Attorney, Nelson 

Pérez-Sosa, Assistant United States Attorney, Chief, Appellate 

Division, and Rosa Emilia Rodríguez-Vélez, United Sates Attorney, 

on brief for appellee. 

July 13, 2015 
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BARRON, Circuit Judge. The defendant in this federal 

gun crime case challenges his sentence on a number of grounds. We 

vacate and remand for resentencing consistent with this opinion. 

I. 

On August 12, 2013, Puerto Rico law enforcement officers 

performed a traffic stop after noticing a driver smoking what 

appeared to be marijuana. The officers asked the driver -- later 

identified as Sergio Santa-Otero, the defendant-appellant here -- 

whether, in addition to the marijuana, there was anything else 

illegal in the car. Santa informed the officers that he had a gun 

and some ammunition inside a black fanny pack. The officers seized 

a loaded Glock pistol from the fanny pack. At some point, Santa 

told the officers not to touch the gun's trigger because the gun 

had a "chip" and thus could fire as an automatic weapon. The 

officers also recovered from the car four loaded Glock pistol 

magazines, two additional loaded high-capacity magazines, and more 

than one hundred .40-caliber rounds of ammunition. 

Federal authorities charged Santa with unlawfully 

possessing a machine gun in violation of 18 U.S.C. §§ 922(o)(1) 

and 924(a)(2), and with unlawfully possessing a firearm as a 

convicted felon in violation of 18 U.S.C. §§ 922(g)(1) and 

924(a)(2). Santa pled guilty to both counts. 

The plea agreement recommended a sentence between 33 and 

41 months in prison, which was the range recommended by the 
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sentencing guidelines assuming that Santa's criminal history 

category was II. The probation office subsequently determined, 

however, that Santa's criminal history category was III, not II, 

and thus that the proper guidelines range for Santa was 37 to 46 

months. 

The District Court did not sentence Santa within even 

that higher range. The District Court instead imposed a sentence 

of 65 months in prison. At the sentencing hearing, the District 

Court explained that, due to the seriousness of the "arsenal" Santa 

possessed at the time of arrest and Santa's "prior convictions at 

the state level," a "nefarious" purpose motivated Santa's unlawful 

possession of the automatic weapon and ammunition. 

One of Santa's two prior convictions was for domestic 

violence. Santa apparently had "[p]unched the woman in the face 

and body, [and] broke[n] her nose." The other conviction was for 

simple possession of controlled substances. The District Court 

repeatedly mischaracterized that conviction, however, as one for 

possession with intent to distribute. Santa now appeals his 

sentence chiefly on the basis of that error.1

 1 Because the District Court did not sentence Santa within 

the terms of the plea agreement, the government rightly 

acknowledges that the agreement's waiver-of-appeal clause does not 

bar the present appeal. 
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II. 

Santa argues that the District Court clearly erred in 

finding that Santa had been convicted of possession with intent to 

distribute controlled substances, when in fact he was convicted of 

simple possession. Santa is right, and even the government now 

concedes the point. The dispute, then, is over the consequences 

of the District Court's error. 

The government contends the error was harmless. To 

decide whether it was, we look to see if the error "affect[ed] the 

district court's selection of the sentence imposed." United States 

v. Tavares, 705 F.3d 4, 26-27 (1st Cir. 2013) (quoting Williams v. 

United States, 503 U.S. 193, 203 (1992)). "If the party defending 

the sentence persuades the court of appeals that the district court 

would have imposed the same sentence absent the erroneous factor, 

then a remand is not required . . . ." Williams, 503 U.S. at 203. 

In contending the error did not affect the sentence, the 

government argues that the error did not alter Santa's criminal 

history category under the sentencing guidelines. Under the 

guidelines, the criminal history category helps to determine the 

recommended sentencing range. But the District Court did not 

impose a sentence within the guidelines range. The District Court 

instead imposed a sentence that varied considerably upwards from 

that guidelines range. The government's argument for why the error 

was harmless is therefore insufficient. 
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Instead, the key question is whether the error affected 

the extent of the variance. As to that point, the District Court, 

in explaining its rationale for the upward variance, expressly 

referenced the supposed drug trafficking offense three times 

during the sentencing hearing. And the District Court, in 

justifying the sentence, both highlighted Santa's "prior 

convictions at the state level" and concluded that "any reasonable 

person can infer [that] a person with [Santa's] history and his 

criminal history, and that amount of ammunition and kind of gun 

and arsenal, . . . had no good purposes or intents by having . . . 

that firearm and those high capacity magazines." (Emphasis added.) 

But the District Court may have viewed Santa's criminal history -

- and the plausibility of his alleged innocent intention for 

possessing the firearm, ammunition, and magazines -- differently 

had it properly understood that the defendant's prior drug 

conviction was for mere possession and not possession with intent 

to distribute. Then again, maybe not. Ultimately, however, while 

Santa's sentence "might well have been the same regardless of" the 

error, given the emphasis the court placed on it "we are not 

certain enough to find harmless error." United States v. McGhee, 

651 F.3d 153, 158 (1st Cir. 2011). We thus cannot say the 

government has met its burden of showing that the District Court's 

mistaken understanding of the defendant's prior drug conviction 
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had no effect on the sentence. See Tavares, 705 F.3d at 26-27. 

We therefore vacate Santa's prison sentence.2

III. 

That leaves one final issue. The District Court orally 

imposed a three-year term of supervised release, but the final 

written judgment purported to impose a five-year supervised 

release term. Santa asks that we vacate the supervised release 

portion of the sentence and remand so that the District Court may 

conform the supervised release term to the term set forth in the 

District Court's oral sentence. Because "an oral sentence prevails 

over a written judgment if there is a material conflict between 

the two," United States v. Riccio, 567 F.3d 39, 40 (1st Cir. 2009), 

the government rightly concedes that the District Court erred in 

imposing the five-year supervised release term set forth in the 

written judgment. We therefore vacate Santa's supervised release 

term so that it may be corrected on remand. 

IV. 

For the reasons provided above, we vacate Santa's prison 

sentence and supervised release term and remand for resentencing. 

 2 Because we reach that conclusion, we need not address 

Santa's separate contention that insufficient evidence supported 

the District Court's conclusion that Santa necessarily had a 

"nefarious" purpose in possessing the weapon and ammunition.