Former Connecticut Resident Sentenced to 90 Months for Operating $4 Million Investment Fraud Scheme, Tax Evasion

David X. Sullivan, United States Attorney for the District of Connecticut, announced that JOHN A. MASANOTTI, JR., 71, of Bonita Springs, Florida, was sentenced today by U.S. District Judge Victor A. Bolden in New Haven to 90 months of imprisonment and three years of supervised release for offenses stemming from an investment fraud scheme.

According to court documents and statements made in court, Masanotti, who formerly resided in Darien, Connecticut, was the owner and managing member of Middlesex Mortgage Group, LLC, also known as Middlesex Group, LLC ("Middlesex"), based in Darien. Through Middlesex and while acting as an investment advisor, Masanotti purported to manage a pooled investment vehicle on behalf of investors. Masanotti claimed to clients and potential clients that invested funds were going to be, and were in fact, pooled together and invested in foreign currency and other investments. Between approximately 2016 and 2023, Masanotti defrauded 14 clients of a total of more than $4 million by using their money for personal expenses, and to pay returns to other clients. Masanotti provided clients with fraudulent monthly account statements from Middlesex that showed fake investment profits.

In addition, for the 2016, 2017, and 2019 through 2022 tax years, Masanotti failed to report to the IRS more than $3 million in income, resulting 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 investigation.

Masanotti has agreed to pay $4,361,632 in restitution to the victims of his crime, and to cooperate with the IRS to pay all 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. Released on a $100,000 bond, he is required to report to prison on March 19.

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. The case was prosecuted by Assistant U.S. Attorney Heather L. Cherry.