United States v. Legassa

Court of Appeals for the First Circuit·Decided July 30, 2025·No. 24-1209·Unpublished

Opinion

Not for Publication in West's Federal Reporter

United States Court of Appeals For the First Circuit

No. 24-1209 UNITED STATES OF AMERICA, Appellee,

v.

ARIEL LEGASSA,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Indira Talwani, U.S. District Judge]

Before

Montecalvo and Aframe, Circuit Judges, and Vélez-Rivé, District Judge.

Leslie Feldman-Rumpler for appellant.

Alexia R. De Vincentis, Assistant U.S. Attorney, with whom Leah B. Foley, U.S. Attorney for the District of Massachusetts, was on brief, for appellee.

July 30, 2025

 Of the District of Puerto Rico, sitting by designation.

AFRAME, Circuit Judge. Ariel Legassa, a former vice president at New England Sports Network ("NESN"), was charged with stealing nearly $600,000 from NESN by setting up a fake company and using it to charge NESN for work that was never done. Based on this conduct, a jury convicted Legassa of seven counts of mail fraud, 18 U.S.C. § 1341, and three counts of money laundering, 18 U.S.C. § 1957. Legassa appeals his conviction, arguing that erroneously admitted evidence tainted the verdict thus requiring a new trial. We affirm.

I. Background

We describe the relevant facts, taking a "balanced approach" to our description of the record. See United States v. Velazquez-Fontanez, 6 F.4th 205, 212 (1st Cir. 2021) (citation and internal quotation marks omitted).

NESN hired Legassa in September 2019 as vice president of digital operations, with a starting annual salary of $255,000 plus bonus compensation. Legassa reported to Raymond Guilbault, NESN's chief operating officer and chief financial officer. Guilbault, in turn, reported to NESN's former chief executive officer, Sean McGrail. This case involves Legassa's conduct in 2021 and early 2022.

Legassa's job duties included budgeting, strategic planning, staffing, and hiring vendors to strengthen NESN's digital capacity. Legassa set the 2021 budget for NESN's digital

operations. That budget allotted a substantial sum to pay outside vendors for various projects such as revamping NESN's website and designing new online products. Ordinarily, when a vendor completed work for NESN's digital operations, it would send an invoice directly to Legassa, who would approve the invoice and submit it for payment through NESN's invoicing system. Any invoice for $50,000 or more required additional approval from Guilbault, while invoices for less than $50,000 required only Legassa's approval. NESN paid approved invoices by paper check, which Guilbault and McGrail personally signed, and which NESN then mailed to the vendors.

In early 2021, Legassa reached an agreement with Alley Interactive, LLC ("Alley NY"), a New York-based vendor, to assist in the development of NESN's website. On March 3, 2021, NESN (through Legassa) and Alley NY signed a master services agreement that governed the work Alley NY would do for NESN. Legassa was Alley NY's only contact at NESN. At Legassa's request, NESN budgeted approximately $1 million to pay Alley NY for services provided in 2021.

Meanwhile, at around the same time, Legassa established a fictitious vendor in Connecticut, which he called Alley Interactive, LLC ("Alley CT"), and which he controlled. On February 8, 2021, he created a new email address, "alleyinteractivellc@gmail.com," for the business. The next day,

he applied for a mailbox in Stamford, Connecticut, and listed "Alley Interactive LLC" on the application. Two days later, he filed a signed certificate of incorporation for Alley CT with the Connecticut Secretary of State, using the newly created mailing and email addresses. And the following week, he opened a business checking account for Alley CT with Santander Bank.

As part of his scheme, Legassa created an Alley CT invoice that looked like an Alley NY invoice. To create the invoice, Legassa emailed Alley NY's chief executive officer to request an Alley NY invoice. This request came more than a month before NESN and Alley NY entered into the master services agreement. Alley NY did not send the invoice, so Legassa followed up a week later. Again, Alley NY did not send an invoice. Finally, on March 4, 2021, a day after NESN and Alley NY signed the master services agreement, Alley NY sent Legassa an invoice. Legassa then altered the invoice by adding the Alley CT address and removing Alley NY's banking information.

Soon after, Legassa began approving and submitting Alley NY invoices for work it performed on NESN's website. At the same time, Legassa also began submitting Alley CT invoices for work that was never performed. To evade any suspicion that might arise from the slightly different vendor names and invoice forms, Legassa told NESN's accounts payable and payroll supervisor that Alley NY and Alley CT were "two entities working together, but separately

incorporated. They plan to merge . . . at the end of the year and they asked me to please create a separate account and send payment [to Alley CT] separately until then."

Legassa submitted a total of eleven Alley CT invoices from March 2021 to January 2022. Guilbault gave the final approval to five of the first six, each of which exceeded $50,000. Legassa alone approved the next three because they each were for $48,500 and thus did not require Guilbault's approval. Finally, Guilbault rejected the last two invoices because, by then, Guilbault knew that Legassa owned Alley CT.

NESN paid the first nine Alley CT invoices through seven checks totaling $575,500. Legassa deposited each check into the Alley CT checking account. He then withdrew money and used it to fund various personal and family expenses, including approximately $250,000 in credit card bills, wires to a joint checking account owned by Legassa and his wife, two car loans, an airplane loan, home improvements, and taxes.

On September 19, 2021, following a threat by Legassa to leave NESN, Guilbault and McGrail increased Legassa's salary to $265,200. Following further negotiating by Legassa, NESN again increased his salary in November 2021 to $325,000. Also in November 2021, Legassa asked NESN's finance department to increase the 2022 Alley NY budget to $1.5 million. The finance department granted that request.

Legassa's scheme crumbled in January 2022, after Alley NY conducted a public records search and discovered both the existence of Alley CT and that Legassa owned the company. Word of this discovery reached NESN, which fired Legassa on January 6, 2022. Thereafter, a grand jury indicted Legassa on seven counts of mail fraud -- one count for each check NESN sent to Alley CT. It also charged him with three counts of money laundering for each withdrawal from the Alley CT checking account that exceeded $10,000. Legassa pleaded not guilty and proceeded to trial.

At trial, the district court allowed the introduction of evidence, sometimes over Legassa's objection, that involved witness characterizations alleged to be improper lay opinion testimony under Federal Rule of Evidence 701. The court also allowed the introduction of evidence, over defense objection, of Legassa's spending and certain bank transfers Legassa made from a personal account after he was fired. Legassa argued, unsuccessfully, that the admission of this latter evidence violated Federal Rules of Evidence 401 and 403, because it was irrelevant or, alternatively, because its unfairly prejudicial effect substantially outweighed its probative value.

As a defense, Legassa alleged that Alley CT was actually a joint effort among him, Guilbault, and McGrail to provide him extra compensation, so he would not leave NESN and thereby set back NESN's progress in digital operations during the COVID

pandemic. Unpersuaded, the jury found Legassa guilty on all ten counts. The district court subsequently sentenced Legassa to forty-two months of imprisonment and ordered that he pay $580,500 in restitution. This timely appeal followed.

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