A Wisconsin couple has struck out twice in a legal battle with the Milwaukee Brewers over a $13,000 raffle prize — so now they’re weighing a trip to the state’s Supreme Court for a third time at bat.
Annette and Matthew Flynn of Kenosha, Wisconsin, sued the team’s charity organization after she was denied the jackpot during the Brewers’ July 7, 2023, home game against the Chicago Cubs at American Family Field in Milwaukee.
“They said I was late. They said I was 66 seconds late,” Annette Flynn told local TV station WISN for a Thursday report.
The Brewers Community Foundation reportedly offered to settle with the Flynns after they filed a lawsuit last year, but the couple said they rejected the deal because it included a gag order.
Neither spokespersons for the team nor the foundation’s lawyers immediately returned inquiries from The Independent on Friday.
The foundation holds a 50/50 raffle at every Brewers home game, and the rules at the time gave the lucky ticket holder half the proceeds on the condition that they claim their prize within the first six outs — one full inning — after the winning ticket number was revealed.
One of the 10 tickets Annette Flynn bought was drawn but she couldn’t see it displayed from her seat, which had the scoreboard behind her, and she also didn’t hear the number announced, according to court papers.
By the time Flynn learned she had the winning ticket and made it to the claim table on the loge level concourse, the deadline at the top of the 7th inning had passed.
Flynn told WISN that an usher mistakenly told her to go to the main level, and security video — that was shared by the family — from inside the stadium reportedly shows her racing through the hallways trying to claim the ticket.
“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.'”
But one of the men “looks back at the TV screen, and he says, ‘Oh no, you weren’t here on time. We called another number.’ I’m like, ‘What do you mean you called another number?'” she added.
In March 2025, the Flynns filed a small claims lawsuit in Milwaukee County Civil Court for the statutory maximum of $10,000 in damages, but the case was dismissed by a judge in December.
The Flynns’ lawyer withdrew midway through those proceedings and they proceeded on their own to file an appeal in January.
In court papers, they argued that their lawsuit shouldn’t have been dismissed because they had a pending motion at the time to force the Brewers to provide additional evidence in the case.
But on Tuesday, Judge Nathan Petrashek of the Wisconsin Court of Appeals – District I upheld the lower court’s decision, ruling that “the clear and unambiguous terms of the Foundation’s official contest rules resolve this case.”
“Under these rules, there is no genuine issue of material fact regarding whether the Flynns won the contest,” Petrashek wrote. “They did not, because the Foundation concluded that Annette was late in presenting the winning ticket.”
Matt Flynn told WISN that he and his wife were considering appealing the case to Wisconsin’s highest court, and that he was still a loyal Brewers fan despite his bitterness over the raffle.
“I don’t hold it against the team. The front office, yeah,” he said.
Since the ill-fated drawing, the Brewers Community Foundation has changed the rules to give winners up to 30 days after each raffle to claim their prizes.
A list of recent results posted on the MLB website also shows that the Flynns lost out on a relatively small jackpot, compared to the $65,427 prize won during the Brewers’ March 25 game against the Chicago White Sox.
