USA Today Network//May 21, 2026//
IN BRIEF
Matthew and Annette Flynn say they’ll never go to another Milwaukee Brewers‘ home game again after a dispute over a 50/50 raffle that unfolded at American Family Field.
The Flynns have been fighting Brewers Community Foundation Inc. in court the last year to reclaim $13,000 in prize money they say they legitimately won during a Brewers home game three years ago.
An appeals court on May 19 disagreed with them. Now, the Kenosha couple says they are thinking about taking the case to the Wisconsin Supreme Court.
“This case was never just about one raffle payout,” said Matthew Flynn, 67. “It became about whether ordinary Brewers fans can have confidence that the process is transparent and fair — especially for fans seated far from the claim location, elderly fans, disabled fans, or fans relying on directions from stadium staff.”
Lawyers for the nonprofit foundation declined comment.
Proceeds from the foundation’s 50/50 raffle benefit more than 200 nonprofits throughout Wisconsin that focus on health, education, recreation and basic needs.
A fan can participate in the raffle by purchasing a $2 ticket at a Brewers home game.
The Brewers Foundation draws a winning raffle number during the middle of the sixth inning, and the number is announced through the public address system and displayed on the scoreboard.
The fan with the winning ticket gets the prize, which is 50% of the net proceeds from the day’s raffle ticket sales.
The raffle contest on July 7, 2023, didn’t go smoothly.
The Brewers were at home to play the Cincinnati Reds, who were leading the NL Central at the time.
Annette Flynn, 59, bought 10 raffle tickets while she was tailgating. In the stadium, she sat in section 234 row 9 seat 9. The scoreboard was behind her.
Court documents say she didn’t immediately see the winning number displayed. Nor did she hear it when the number was announced.
At some point, Annette Flynn, a candidate for Kenosha County supervisor in 2024, learned she was the one with the winning ticket.
Rules of the raffle at the time required the person with the winning ticket to claim their prize at a 50/50 table on the loge level concourse. The winner was given “until the end of the top of the 7th inning (or until the third out is recorded in the top of the inning)” to do so.
Annette Flynn asked an usher where to go and was eventually directed to field level guest services.
She was told by foundation officials when she reached the 50/50 table that she didn’t get there in time. A new winning ticket already had been drawn and announced, court filings show.
The other person ended up getting the $13,000 prize payout.
In an interview with the Milwaukee Journal Sentinel, the couple disputes the foundation’s assertion Annette Flynn was late to the table. They claimed she was misdirected.
“Once I found the winning number, I went to the usher in my section … to ask where I needed to go to claim the prize,” Annette Flynn said. “They told me to go down the ramp to guest services behind home plate to claim the prize. We were on the right level to begin with.”
The Flynns sued the foundation in small-claims court, alleging they were wrongfully denied the winnings. State law would have capped money judgments in small-claims court at $10,000 had they won.
A judge there ruled against the Flynns, and the couple later appealed.
The appeals court concurred that the Foundation’s contests rules are clear and failure to “claim the prize by the stated time and in stated manner” results in disqualification and forfeiture of the prize
According to the Flynns, the video footage they received during discovery does not conclusively support the foundation’s version of events. It, instead, raises significant questions regarding the sequence and timing of Annette Flynn’s efforts to claim the prize after being directed by stadium personnel away from the designated claim location, they said.
The Flynns said in the interview they are considering bringing their case to the state Supreme Court, if need be. They also are hoping state gaming officials can step in and examine what happened and, perhaps, recommend changes.
Until then, the couple says they are done with catching home games.
Annette Flynn has been a Brewers fan since 1982, but says she no longer has any interest in having anything to do with the team.
Matthew Flynn had been a Brewer loyalist since 1970, when the team came to Wisconsin from Seattle.
They’re now content with seeing their favorite team in visitors’ jerseys from here out.
“We just went to see the Brewers beat the Cubs in Chicago. We’ll always be [Brewers] fans and will always root for them,” Matthew Flynn said. “But we’ll never go back to American Family Field. Ever. Not after this.”