A former Connecticut resident has been sentenced to 90 months in prison for operating an investment fraud scheme and committing tax evasion. John A. Masanotti, Jr., 71, of Bonita Springs, Florida, received the sentence from U.S. District Judge Victor A. Bolden in New Haven.
David X. Sullivan, United States Attorney for the District of Connecticut, announced the sentencing and detailed Masanotti's actions as owner and managing member of Middlesex Mortgage Group, LLC (also known as Middlesex Group, LLC), based in Darien, Connecticut. According to court documents and statements made in court, Masanotti acted as an investment advisor and told clients that their funds would be pooled together and invested in foreign currency and other investments.
Between 2016 and 2023, Masanotti defrauded 14 clients out of more than $4 million by using their money for personal expenses and to pay returns to other clients. He also provided fraudulent monthly account statements showing fake profits.
For several tax years—2016, 2017, and from 2019 through 2022—Masanotti failed to report over $3 million in income to the IRS. This resulted in a tax loss of nearly $1 million. Additionally, he made false statements to the FBI during the investigation and filed false records to obstruct it.
"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."
He 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 is required to report to prison on March 19.
The case was investigated by multiple agencies including the Federal Bureau of Investigation; Internal Revenue Service Criminal Investigation Division; U.S. Postal Inspection Service; with assistance from the U.S. Securities and Exchange Commission. Assistant U.S. Attorney Heather L. Cherry prosecuted the case.
