Darien Manager: 90-Month Fraud Term

Darien Investment Manager Sentenced to 90 Months for $4M Fraud

John Masanotti Jr. defrauded 14 clients through his Darien firm and lied to FBI investigators

The IRS would to like to remind the public that these hands are rated E: for everyone

Darien Investment Manager Sentenced in New Haven Federal Court

A Florida man who once ran a Darien investment firm was sentenced to 90 months in federal prison on February 17, 2026, after defrauding 14 clients of more than $4 million over seven years and lying to federal investigators during the inquiry.

U.S. District Judge Victor A. Bolden imposed the sentence in New Haven federal court on John A. Masanotti Jr., 70, of Bonita Springs, Florida, who formerly resided in Darien. Masanotti was also ordered to pay $4,361,632 in restitution to his victims and will serve three years of supervised release following his release from prison. He must report to authorities by March 19, 2026.

How the Scheme Worked

Masanotti was the owner and managing member of Middlesex Mortgage Group LLC, also doing business as Middlesex Group LLC, a Darien-based firm that he marketed as managing a pooled investment vehicle on behalf of clients. Between approximately 2016 and 2023, he defrauded those clients by diverting their funds for personal expenses and using new investor money to pay fictitious returns to existing clients — a hallmark of Ponzi-style fraud.

To conceal the losses, Masanotti provided clients with fraudulent monthly account statements from Middlesex that showed fabricated investment profits. The 14 victims collectively lost more than $4 million.

Tax Evasion and Obstruction

In parallel, Masanotti failed to report more than $3 million in income to the IRS across multiple tax years — specifically 2016, 2017, and 2019 through 2022 — resulting in a tax loss to the federal government of nearly $1 million. Prosecutors said he also made false statements to FBI agents during the investigation and filed fraudulent records in an attempt to obstruct the inquiry.

As part of his plea agreement, Masanotti must cooperate fully with the IRS to pay all outstanding back taxes, penalties, and interest in addition to the victim restitution.

Guilty Plea

Masanotti pleaded guilty on October 1, 2025, to one count of wire fraud and one count of tax evasion. The case was prosecuted by the office of U.S. Attorney David X. Sullivan and investigated jointly by the FBI and the IRS Criminal Investigation Division.

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