NEW HAVEN – A former Darien mortgage company owner and investment adviser has been sentenced by a U.S. District judge to more than 7 years in prison and three years of supervised release for perpetrating an investment fraud scheme, according to the U.S. Attorney for the District of Connecticut David Sullivan.
John Masanotti, 71, of Bonita Springs, Florida, and formerly of Darien, also 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.
According to court documents and statements made in court, Masanott was the owner and managing member of Darien-based Middlesex Mortgage Group LLC, also known as Middlesex Group LLC.
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 was arrested on May 9, 2024, and pleaded guilty he pleaded guilty to one count of wire fraud and one count of tax evasion on Oct. 1, 2025. Released on a $100,000 bond, he is required to report to prison on March 19.
