A former Connecticut resident has been sentenced to 90 months in federal prison for running a multi-million dollar investment fraud scheme and evading taxes. John A. Masanotti, Jr., 71, of Bonita Springs, Florida, received the sentence from U.S. District Judge Victor A. Bolden in New Haven.
According to court documents and statements made in court, Masanotti previously lived in Darien, Connecticut, where he owned and managed Middlesex Mortgage Group, LLC, also known as Middlesex Group, LLC. While acting as an investment advisor through this company, Masanotti told clients that their funds would be pooled and invested in foreign currency and other assets.
Between 2016 and 2023, Masanotti defrauded 14 clients out of more than $4 million by using their money for personal expenses and paying returns to other clients. He provided fraudulent monthly account statements showing fake profits.
For the tax years 2016, 2017, and from 2019 through 2022, Masanotti did not report over $3 million in income to the IRS. This resulted in a tax loss of nearly $1 million.
Masanotti also made false statements to the FBI during the investigation and filed false records in an attempt to obstruct the inquiry.
He has agreed to pay $4,361,632 in restitution to his victims and cooperate with the IRS on back taxes, penalties, and interest.
Masanotti was arrested on May 9, 2024. On October 1, 2025, he pleaded guilty to one count of wire fraud and one count of tax evasion. He had been released on a $100,000 bond but must report to prison on March 19.
The Federal Bureau of Investigation led the investigation along with the Internal Revenue Service’s Criminal Investigation Division and the U.S. Postal Inspection Service. The U.S. Securities and Exchange Commission also assisted. Assistant U.S. Attorney Heather L. Cherry prosecuted the case.
“This matter was investigated by the Federal Bureau of Investigation, the Internal Revenue Service, Criminal Investigation Division; and the U.S. Postal Inspection Service; with the assistance of the U.S. Securities and Exchange Commission,” according to officials.
