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A Kenosha couple’s long-term dispute with the Milwaukee Brewers has escalated into a formal legal action. The Brewers’ denial of the winning amount was deemed unfair by the fans, and the controversy has now sparked a much wider criticism against the franchise. 

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“They said I was late. They said I was 66 seconds late,” said Annette Flynn to explain the reason for the denial. 

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Annette and Matthew Flynn bought a 50/50 raffle ticket in the parking lot of American Family Field on July 7, 2023. They were supposed to get $13,000 as winners, but the franchise informed them that they arrived after the deadline. And now the fan couple is going for a formal lawsuit against the franchise. 

According to the rules, half of the money would go to the one with the winning numbers, while the remaining half would go to the Brewers Charity Foundation. So the Flynns earned their share when their ticket number was announced. Unfortunately, they missed the first announcement. By the time they realized it was their ticket that won the prize, they rushed to the designated spot. But again, they hit a roadblock. An usher directed them to the main floor. They were supposed to get to the loge level. 

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“So I caught my breath, and then I proceeded to walk up 57 steps to the second floor. Out of breath, completely. I get to the table upstairs, and two gentlemen are there,” Annett added.

She showed the ticket and the message she received on her phone to claim the prize. But they told her that she was a bit late. The couple needed to reach the spot before the sixth out in the game. And given their original seat, it was an incredibly tough task. 

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“Why would anybody buy a 50/50 raffle ticket under those conditions?” a fan asked the obvious question. 

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The main purpose of the lottery is charity. Some fans believe that having strict rules simply means an unwillingness on the part of the authority. And if you are an elderly or a disabled person, you can simply forget about the winning prize. 

Fans immediately questioned the fairness of the policy, especially for elderly or disabled attendees. The Brewers’ strict timeline was unusually harsh compared to standard MLB 50/50 raffle protocols. For example, the Los Angeles Dodgers allow fans to claim their prize anytime before the game ends, and many other MLB franchises offer a standard 30-day window

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The most frustrating part was the couple’s experience in the small-claims court. After they explained the scenario, the court rejected their claim, pointing out that the organization has sole discretion in awarding the prize. This means they can refuse to hand out the prize money for any reason. That’s why the fan couple is moving to a higher court for a formal lawsuit. 

“They are going to miss out on more than 13k in future sale proceeds now. Who is going to buy in now after reading this story? Extremely dumb by the brewers,” commented another fan. 

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Many considered the denial a cheap move by the Brewers. The amount wasn’t too big, but the way they handled it didn’t paint a pretty picture for the diehards. However, the franchise did try to make amends. 

Brewers changed the rules after the controversy 

The authorities told the Flynns that they announced a different ticket number as the couple wasn’t there on time. However, Annette and Matt have now acquired a video from the Brewers that shows how they rushed to the spot. 

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The Brewers Community Foundation timeline shows they waited just 15 seconds after the final out before posting that other winning number. It is easy to understand why many fans straightaway criticized the franchise. However, the Brewers have changed the 6 outs rules since then. The winner of a 50/50 raffle can now claim the winning money in 30 days. 

According to the Flynns, they even offered a settlement to the couple. But it came with a gag order. Matt and Annette couldn’t agree to that. That’s why they are standing firm on the lawsuit. 

While the organization tried to recover from the fan backlash, it didn’t really succeed. But that doesn’t mean that the baseball team has lost some fans. Matt Flynn was still wearing a Brewers T-shirt, as seen in the video shared by American Crime Stories. 

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“I don’t hold it against the team, the front office? Yeah,” he added. 

The change in the rule looks like a win for the couple, even though it’s a small one. But the Milwaukee Brewers have a lot to lose here while trying to save an amount that is merely a fraction of their payroll from this season. It is the faith of their loyalists. And it’s not something they can just earn even if they win the NL Central crown.

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Ritabrata Chakrabarti

191 Articles

Ritabrata Chakrabarti is an MLB journalist at EssentiallySports, covering Major League Baseball from the MLB GameDay Desk. With an engineering background that sharpens his analytical lens, he focuses on game development, strategic breakdowns, and league-wide trends that shape the season on a daily basis. With over three years of experience in digital content, Ritabrata has worked across editorial leadership and quality control roles, developing a strong command over accuracy, structure, and storytelling under fast-paced publishing cycles. His MLB reporting goes beyond surface-level analysis, offering fan-oriented explanations of individual and team performances, in-game decisions, and roster moves. Ritabrata closely tracks daily storylines by connecting on-field performances with broader seasonal arcs and offseason activity, helping readers make sense of both the immediate moment and the long view.

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Arunaditya Aima

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