A low-key visit to a Martha’s Vineyard veterans post just turned into a generational windfall. The 2026 Dad and Daughters Trust of Vineyard Haven has claimed a $15 million top prize from the Massachusetts State Lottery after buying a winning scratch ticket on the island. Trustee John Kennan Jr. chose a one-time lump-sum payment of $9,750,000 before taxes, according to the trust’s representative. The ticket was sold at VFW Post 9261 in Oak Bluffs, which will collect a $50,000 retailer bonus for selling the winner.
According to Boston 25 News, lottery officials identified the claimant as the "2026 Dad and Daughters Trust of Vineyard Haven" and confirmed this was the third and final $15 million grand prize in the state’s "Millions" instant ticket game. The outlet also quoted the trustee saying the winners plan to put the money toward family needs, keeping the focus close to home.
Prize-tracking data compiled from official Lottery reports showed that the $30 instant game carrying a $15 million top prize had only one such top prize left as of March 29, 2026, which means this claim likely wiped out the game’s highest remaining award. ScratchSmarter maintains a daily rundown of top prizes and odds for Massachusetts instant tickets.
VFW post and island reaction
The winning ticket came from VFW Post 9261 at 14 Towanticut Avenue in Oak Bluffs, a longtime island hangout that doubles as a hub for community events and fundraisers, according to local listings. The post will receive a $50,000 retailer bonus tied to the sale, a solid payday for a neighborhood gathering spot, as noted by Boston 25 News. Event schedules and the post’s address are listed in the Vineyard Gazette community calendar.
How winners and retailers are paid
Large instant-ticket winners frequently steer away from annuities and go straight for lump-sum payouts. In this case, the trust took a single $9.75 million payment before taxes, the claim representative said. Retailers that sell top-prize tickets are also rewarded, typically with a $50,000 bonus on a $15 million win. That same pattern showed up when a DAO Trust claimed a different $15 million ticket sold in Sterling last year. Yahoo reported on that earlier prize and the related retailer payment.
The Massachusetts Lottery returns its revenue to the commonwealth for services that include education and grants, with instant tickets supplying a major share of those dollars. WBUR reported in 2025 that scratch games made up most Lottery sales and helped fuel strong profits for state programs. On the island, locals said they were pleased to see the VFW land a sizable bonus and to hear that a Vineyard-based trust turned a routine scratch-off into a genuinely life-changing moment.
