Westport investment advisor pleads guilty to federal tax charge


Date: January 5, 2023

Contact: newsroom@ci.irs.gov

Vanessa Roberts Avery, United States Attorney for the District of Connecticut, and Joleen D. Simpson, Special Agent in Charge of IRS Criminal Investigation in New England, announced that Thomas Pacilio, of Westport, waived his right to be indicted and pleaded guilty today before U.S. District Judge Sarala V. Nagala in Hartford to a federal tax offense.

According to court documents and statements made in court, in 2011, Pacilio and his partner started Clapboard Hill Advisors LLC, a financial services business headquartered in Westport. In 2013, Pacilio created Alcamo Holding Corporation Inc. ("Alcamo"), an 1120S corporation, and transferred his Clapboard Hill Advisors partnership interest to Alcamo. In 2014, Pacilio, through Alcamo, and his partner, through a separate 1120S corporation, sold Clapboard Hill Advisors to McGladrey Wealth Management LLC ("McGladrey"). Under the sale agreement, McGladrey agreed to make a lump sum payment at closing. Thereafter, Pacilio was to become an employee of McGladrey for three years subject to a non-competition provision. In addition to being paid a salary by McGladrey, if Pacilio remained an employee, Pacilio would receive a $350,000 payment on each anniversary of the sale for three years. He would also receive a portion of McGladrey's annual gross revenue of up to $150,000 for the first year, $350,000 for the second year, and $450,000 for the third year.

In pleading guilty, Pacilio admitted that, for the 2015 through 2018 tax years, he filed individual income tax returns that omitted installment payments related to the sale of Clapboard Hill Advisors to McGladrey. In total, he omitted approximately $1,476,425 that should have been reported either as ordinary income or as capital gains, which resulted in a tax loss of $286,328 to the IRS.

Pacilio pleaded guilty to one count of filing a false tax return, an offense that carries a maximum term of imprisonment of three years. Judge Nagala scheduled sentencing for April 6.

Pacilio is released on a $350,000 pending sentencing.

This investigation is being conducted by the Internal Revenue Service, Criminal Investigation Division. The case is being prosecuted by Assistant U.S. Attorney Heather L. Cherry.