A Wisconsin couple has struck out twice in their legal battle with the Milwaukee Brewers over a $13,000 raffle prize, and they are now considering an appeal to the state's Supreme Court for a third attempt.
The Raffle Incident
Annette and Matthew Flynn of Kenosha, Wisconsin, sued the Brewers Community Foundation after Annette was denied the jackpot during a July 7, 2023, home game against the Chicago Cubs at American Family Field. The foundation holds a 50/50 raffle at every home game, with winners required to claim their prize within the first six outs—one full inning—after the winning number is announced.
Annette Flynn bought 10 tickets, and one was drawn. However, she could not see the display from her seat, which had the scoreboard behind her, and did not hear the number announced. By the time she learned she had the winning ticket and reached the claim table, the deadline had passed. She told local TV station WISN that an usher mistakenly directed her to the main level, and security footage shows her racing through the hallways. “I caught my breath, and then I proceeded to walk up 57 steps to the second floor,” she said. “Out of breath completely, I get to the table upstairs, two gentlemen are there, I show them my phone and my ticket, and I said, 'I'm the winner, Bob downstairs sent me up here.'” One of the men checked a TV screen and said, “Oh no, you weren't here on time. We called another number.”
Legal Proceedings
In March 2025, the Flynns filed a small claims lawsuit for the statutory maximum of $10,000 in damages, but the case was dismissed in December. Their lawyer withdrew, and they proceeded on their own to file an appeal in January. They argued the dismissal was improper because they had a pending motion to compel the Brewers to provide additional evidence. However, on Tuesday, Judge Nathan Petrashek of the Wisconsin Court of Appeals upheld the lower court's decision, ruling that “the clear and unambiguous terms of the Foundation’s official contest rules resolve this case.” He wrote, “Under these rules, there is no genuine issue of material fact regarding whether the Flynns won the contest. They did not, because the Foundation concluded that Annette was late in presenting the winning ticket.”
Ongoing Fight
The Brewers Community Foundation reportedly offered to settle after the lawsuit was filed, but the Flynns rejected the deal due to a gag order. Matt Flynn told WISN that he and his wife are considering appealing to the Wisconsin Supreme Court. Despite his bitterness, he remains a loyal Brewers fan. “I don’t hold it against the team. The front office, yeah,” he said. Since the incident, the foundation has changed the rules to give winners up to 30 days to claim prizes. Notably, the $13,000 prize the Flynns lost is relatively small compared to the $65,427 jackpot won during a March 25 game against the Chicago White Sox.
