Nearly winning has a certain cruelty to it. It’s probably worse than not winning at all, according to Annette Flynn of Kenosha, Wisconsin. She was watching the Brewers play the Chicago Cubs at American Family Field in Milwaukee on the evening of July 7, 2023, while holding one of ten 50/50 raffle tickets. The winning ticket was one of those. She owned it. She still didn’t have a dime when she returned home.
A rule was established by the Brewers Community Foundation, the nonprofit organization of the team that hosts these raffles during home games. After the winning number was revealed, winners had to pick up their prize within the first six outs. One complete inning is that. Breathless after ascending 57 steps, Annette Flynn reached the claim table on the loge level concourse sixty-six seconds after that window closed. The foundation declined.
What allegedly transpired between the announcement and her arrival is what elevates this tale beyond simple hardship. Flynn claims that because the scoreboard was behind her section and she didn’t hear any announcements, she was unable to even see the winning number from her seat. The clock was already working against her when someone nearby informed her that she had won. The family claims that an usher then led her to the completely incorrect level.
According to security footage, she can be seen racing through stadium hallways in an attempt to find the correct table. “I caught my breath, and then I proceeded to walk up 57 steps to the second floor,” she said to WISN, a local television station. “Breathless, I reach the table upstairs, where two gentlemen are present. I declare, ‘I’m the winner, Bob downstairs sent me up here.'”
In March 2025, she and her spouse, Matthew, sued the Brewers Community Foundation. During the proceedings, the foundation made a settlement offer, but the Flynns rejected it. Why? a mandatory gag order. That choice reveals that the couple is no longer merely pursuing financial gain. They appear to want the story to be told. Depending on which side of the debate you were on that evening, that may or may not be praiseworthy.
Recently, the Wisconsin appeals court decided against them, supporting the foundation’s argument that Flynn should not have received the prize because he arrived too late. Now it’s two losses. It’s still unclear if that decision represents a clear application of contract law or something more awkward, such as a major sports organization enforcing fine print with a rigidity that most reasonable fans probably wouldn’t expect from a charity raffle. The Flynns are currently considering their third attempt at an appeal to the Wisconsin Supreme Court.
It’s difficult to ignore the significance of the minute details as you watch this develop. The stadium usher’s deception. the location of the scoreboard. 57 steps. These are the kinds of details that stick with you, but none of those facts seem to have had much of an impact on the court. These individuals weren’t attempting to manipulate a system; rather, they were rushing through a stadium and missed by a little more than a minute.
This entire incident is genuinely awkward because the foundation raises funds for over 200 nonprofits in Wisconsin. Even if the legal position is upheld, it’s odd to see a charity organization standing firm on a technicality against a middle-aged couple from Kenosha, with lawyers and courtrooms now involved. The Flynns have already ensured that the story goes far beyond American Family Field, regardless of whether the Wisconsin Supreme Court agrees to hear the case.
