Westport Financial Advisor Pleads Guilty In $1.5M Federal Tax Case

WESTPORT, CT — A 64-year-old Westport man waived his right to be indicted and pleaded guilty this week to a federal tax offense, announced United States Attorney Vanessa Roberts Avery, and Joleen D. Simpson, Special Agent in Charge of IRS Criminal Investigation in New England.

Thomas Pacilio pleaded guilty Thursday to one count of filing a false tax return before U.S. District Judge Sarala V. Nagala in Hartford. He is currently free on a $350,000 bond pending sentencing, which is scheduled for April 6.

According to court documents and statements, Pacilio admitted he omitted reporting approximately $1,476,425 in income from the sale of his business.

Pacilio and his partner started Clapboard Hill Advisors LLC in 2011, a financial services business headquartered in Westport. In 2013, he created Alcamo Holding Corporation Inc. ("Alcamo"), an 1120S corporation, and transferred his Clapboard Hill Advisors partnership interest to Alcamo, according to prosecutors.

In 2014, through Alcamo, Pacilio and his partner, used a separate 1120S corporation, to sell 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, prosecutors said.

Pacilio 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 his guilty plea, 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, by not reporting the money either as ordinary income or as capital gains, the IRS lost $286,328 in taxes, according to prosecutors.

The offense that Pacilio pleaded guilty to carries a maximum prison term of three years.

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.