Massachusetts attorney accused of stealing inheritance, faces legal reckoning

Melrose, Massachusetts – A prominent attorney, Henry Rappa, is facing embezzlement and larceny charges after allegedly misappropriating hundreds of thousands of dollars entrusted to him by a couple, Michael and Jannine Tipping, who were navigating a complex family inheritance. The case, now unfolding in Middlesex County, underscores a disturbing breach of trust and raises questions about oversight within the legal profession.

A family inheritance turns sour

The Tippings inherited a substantial sum following the unexpected death of Michael's mother. Initially, his sister served as the trustee, but her untimely passing necessitated a swift search for a replacement. Jannine Tipping diligently researched potential legal counsel, ultimately selecting Rappa. In March 2023, the couple transferred their inherited funds to Rappa's care, a decision they now deeply regret. What followed, according to their attorney Charles Dobens, was a rapid dissipation of their assets.

“We learned at his hearing that my client's money was gone almost immediately,” Dobens stated, highlighting the speed with which the funds vanished. The couple’s repeated requests for invoices documenting Rappa’s work were consistently met with evasive excuses. Jannine Tipping recounted a litany of deferrals, ranging from feigned illness to urgent care visits, and even a last-minute excuse involving Opening Day Red Sox tickets. “Every time we asked for an invoice… it was always, 'well someone is actually working on my books,'” she explained.

The situation reached a critical point when the Tippings decided to purchase a new home and requested a full accounting of the funds. Rappa’s request—to know how much money they actually needed—proved to be the tipping point, according to Jannine. “That's when I thought we are going to have a significant problem.”

While the road to recovery remains, Dobens expresses optimism that his clients will be made whole. “Massachusetts is one of the unique states that actually has a financial vehicle to make whole any person that has been hurt by a bad lawyer,” he noted, contrasting the state’s protections with those offered in other jurisdictions.

Adding insult to injury, a court order issued in July 2025 prohibited Rappa from practicing law. Yet, he allegedly continued to represent clients, culminating in accusations of stealing $21,000 from another client during a real estate closing. Rappa’s attorney has yet to respond to requests for comment from WBZ.

The case serves as a stark reminder of the vulnerabilities inherent in entrusting significant sums of money to legal professionals, and the crucial role of robust oversight in safeguarding client assets. The Board of Bar Overseers' permanent suspension of Rappa's license may finally pave the way for the Tippings to reclaim what was lost, but the emotional toll of this betrayal will likely linger long after the legal battles conclude.