MILWAUKEE, Wis. — Matt and Annette Flynn, of Kenosha, have spent decades rooting for the Milwaukee Brewers. But now, the team they’ve supported for generations is at the center of a legal battle over a $12,849 raffle prize the couple says they rightfully won—and were wrongly denied.

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The saga began on July 7, 2023, when the Flynns were tailgating outside American Family Field, like they had nearly 100 times before. A man in an orange vest approached Annette in the lot and asked if she wanted to buy tickets for the Brewers’ 50/50 raffle. She handed him $20 and received 10 tickets.

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Annette asked how the winning number would be announced—an important detail, since she’d missed it during a previous game. The vendor told her the number would be posted on the scoreboard following the sixth-inning sausage race. The 50/50 raffle is a familiar tradition: half the pot goes to the winning ticket holder, and the other half to charity. That night, the winner’s half of the prize pool reached $12,849.

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Annette and Matt, seated in Section 234 under Bernie the Brewer’s slide, were watching as the sixth inning quickly unfolded—a result of Major League Baseball’s newly implemented pitch clock that year. They didn’t spot the winning number on the scoreboard, but a nearby fan advised Annette to check the Brewers’ website. She did—and gasped. Her ticket, 5632027, was the winner.

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The fan warned that she had only until the end of the top of the seventh inning to claim the prize. Annette immediately took off running. Matt followed behind at a walking pace. An usher told them to head down the ramp toward Guest Services behind home plate. This would turn out to be a much longer path, twice as far, say the Flynns. A sheriff’s deputy confirmed Annette was heading in the right direction.

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Annette, out of breath, reached Guest Services and said, “I won the 50/50 and I’m here.” A staffer reassured her, told her to calm down, and pointed her up another 57 stairs to the actual 50/50 desk. Believing she had done what was required by reaching Guest Services before the end of the top of the seventh, Annette walked the final stretch.

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But when she presented her winning ticket at the desk, the response floored her: “Sorry, ma’am, you’re late. We called another number.” According to Brewers officials, Annette reached the desk 67 seconds too late. But the Flynns strongly dispute that account—both the timeline and the logic.

Matt, who saw the final out of the top of the seventh inning with his own eyes, says he’s certain Annette had already reached Guest Services by that time. More puzzling, the timestamp data provided by the Brewers appears to show that Matt, walking, arrived at Guest Services before Annette—who had sprinted the entire route.

“It just doesn’t add up,” Annette told Kenosha County Eye. “I ran as fast as I could. There’s no way Matt got there before me unless something about their timestamps is way off.” Adding to their frustration, the Flynns say they witnessed 50/50 raffle staff selling tickets to visibly handicapped fans seated in the accessible section—individuals who would have had no realistic way of reaching Guest Services in time under the one-inning rule. They found the practice not just impractical, but cruel.

The couple contacted Brewers management that night. A representative promised to review stadium footage and call them the next day. The call never came. After repeated attempts to follow up, the Flynns retained Kenosha-based attorney Todd Terry of Terry & Nudo. Terry sent a letter to the Brewers Community Foundation on July 13, 2023, demanding the team preserve all video evidence and asserting Annette’s claim to the winnings. He noted that the shortened pace of play created by the pitch clock made it nearly impossible for fans in outfield sections to reach Guest Services within one inning—especially without clearly marked procedures.

Weeks later, the Brewers allowed Matt, Annette, and Attorney Terry to view selected surveillance video during a closed-door meeting with a team attorney and technician. Matt was initially told he wasn’t allowed to be in the room—but he went in anyway. The team showed them the footage on a small laptop screen. They weren’t allowed to photograph or record the screen. The timestamp data was unreadable. They were only shown select clips—not Annette’s full sprint through the concourse, nor any footage of the so-called “exciting moment” that Brewers officials later claimed caused her to stop along the way.

“They said I paused to watch the game,” Annette said. “I absolutely didn’t. I was running the whole way.” On March 12, 2025, the Flynns filed suit in Milwaukee County Circuit Court. At an April 7 hearing, a court commissioner ordered the Brewers to turn over all videos and documents. The Brewers reportedly made a lowball settlement offer—“a couple grand and some tickets,” according to the Flynns—but they rejected it.

“We’re not doing this for the money,” Annette said. “We want the truth—and accountability.” Since the incident, the Brewers have quietly changed their 50/50 raffle policy. Winners now have 30 days to claim their prize. The Flynns also brought their story to investigative reporter Jenna Sachs of Fox6. Sachs spent nearly two hours interviewing them on camera and said she planned to attend the 2024 season opener to investigate. But the segment never aired. Sachs later told the Flynns, “I wrote the script weeks ago but it hasn’t been scheduled. I wish I could share more info, but I’m not sure it’s going to air.”

Kenosha County Eye also reached out to the Milwaukee Brewers multiple times seeking comment for this story. The team never responded. The Flynns believe Sachs wanted to report the story but was silenced by higher-ups. Now, nearly two years after the game, the Flynns are still fighting—not for a check, but for the principle.

“If they think we’re going to forget this,” Annette said, “they picked the wrong fans.”