Quincy Attorney Represents His 50th Lottery Winner

Attorney David Spillane of Quincy, Trustee of the Tommy D Nominee Trust, collecting winnings for a $10 Million winner on New Year’s Eve at Massachusetts Lottery Headquarters in Dorchester sporting a New Year’s tie. Courtesy Photo

Folks wonder how David Spillane can be so lucky. A thorough review of the Massachusetts State Lottery website will show Spillane cashing major prize winnings at the Lottery an amazing Fifty times! It’s because Spillane, an attorney who practices in Quincy and Hanover, represents winners of the Lottery who wish to remain anonymous.

“People keep asking me, ‘How can you be so lucky?’” Spillane mused. He always shares the “secret of success” with a whisper in the ear: “Buy a ticket!”

Spillane spent part of New Year’s Eve collecting a $10 Million prize for a scratch ticket winner who then had the greatest New Year’s Celebration of his life. That was Spillane’s fiftieth time going to the lottery for his lucky clients since he started doing it back in 2015. He breaks his own record with each new Lottery client.

His first Lottery client was referred by a friend, who was speaking with a North Shore minister who won a $1,000,000 Lottery prize on a scratch ticket, but who did not want his parishioners to know he won. It was not so much that he was worried about them wanting to borrow money from him, but more so because gambling is against his religion. He didn’t want them to know he was breaking a rule he preaches.

“I have had three multi-major prize winners who won twice each, and one who won three times! All of them are still scratching, hoping that lightning will continue to strike,” said Spillane, who lives in Quincy. Winners have included two doctors and an Ivy League professor, as well as others from all walks of life. “I’ve had four winners from out of state, one who lives one block from my son’s apartment in New York and who coincidentally grew up a few blocks from my childhood home in Dorchester.” Small world.

Several people told no one that they were lottery winners, except for Spillane. One couple from Worcester who won $1,000,000 said they weren’t telling their children, so Spillane asked them if it was going to change their lifestyle, which would have been a giveaway to their kids. “They told me that they were contemplating purchasing a vacation home in the mountains, and that they would simply buy a little nicer home with a little smaller mortgage,” Spillane explained. “I asked them if they would invite me to the cookout when they were going to tell their children so I could see the looks on their faces.”

Spillane’s Lottery clients are typically $1,000,000 winners, but he has had one $15,000,000 winner (a couple in their thirties with two small children), three $10,000,000 winners, and multiple $4,000,000 winners. “The lowest amount I ever collected for winners was $100,000,” Spillane said. “It was hardly worth the expense, considering the after-tax net payout, but she told me that she had a fiancé who hung around a bar, and that if he and his friends found out about the winnings, they would pressure her to share it with them. My advice to her was to shop around for a new fiancé.”

Spillane has represented winners from every corner of Massachusetts, from Chicopee to Amesbury to New Bedford. A Cape Cod winner hit for $4,000,000, and decided to take the annuity, which will pay her $200,000 per year for twenty years. It represented about five times as much per year a she had ever earned. She said she was going to retire and spend her time caring for, and spoiling, her first grandchild.

“Most people who win the Lottery and retain us to collect their winnings anonymously are not used to having large sums of money,” said Spillane. “My advice to them is always to engage the services of a financial planner and establish an estate plan. About 60% of them come back to us  to create an estate plan for them.” The majority of Spillane’s practice relates to estate planning and real estate.

A $4 Million winner from Hingham who had won the Lottery twice said he wasn’t going to tell his only child about his good luck. He plans to keep working at his family business, with his only indulgence being to purchase a new boat. He wants to give his daughter a nice surprise when he passes on.

One lucky winner from Worcester thought he had won $1,000,000 on a game called 100X CASHWORD. He had put off scratching a portion of the ticket that indicates whether there is a multiplier on the face amount. When he came into Spillane’s office, he scratched it realized to his glee that he had actually won $2,000,000.

“I always ask the client what they would like to name their trusts,” explained Spillane. “Some want to use a combination of initials, but I encourage them to have a little fun with the naming of the trust, Spillane said. “I typically suggest to name the trust after something to do with a super hero.” Other names have included a character from a movie (The latest trust was called the Tommy D Trust after Joe Pecci’s character in Goodfellas). “One couple from Framingham brought their two little girls with them to my office,” Spillane recounted, smiling, “so I suggested we call the trust the Two Cuties Trust.”

No one else in the history of the Massachusetts Lottery has collected more winnings for clients under a trust that David Spillane. In total, Spillane has collected a face value of over $100 Million for his very lucky clients.

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