MILWAUKEE, Wis. — After Kenosha County Eye became the first news outlet to report on Matt and Annette Flynn’s dispute with the Milwaukee Brewers Community Foundation over a $12,849 50/50 raffle prize, the story spread to Milwaukee television stations and other media outlets. Now, as the Kenosha couple asks the Wisconsin Supreme Court to review their case, newly disclosed emails reveal that Tyler Barnes, the Milwaukee Brewers’ Senior Vice President of Communications and Affiliate Operations, privately urged a television station not to air a story about the controversy.

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Barnes made the request on May 20, 2025, after CBS58 contacted the Brewers for comment regarding the Flynn lawsuit. According to emails disclosed during litigation, Barnes wrote that the Flynns “continue to beat the media drum despite the evidence firmly backing our position” before adding, “Our hope is that the story does not air — it’s just not productive to discuss through public channels.” Despite Barnes’ request, CBS58 ultimately aired its report on the dispute. The emails provide a rare look at how Brewers officials responded to media inquiries while coverage of the dispute was being considered.

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Notably, Barnes did not send his response to the CBS58 assignment editor who requested comment. Instead, he directed the email to Anne Brown, Vice President and General Manager of CBS58, writing that while his inclination was not to respond to the reporter, the Brewers would provide a statement “out of respect for you and others at CBS-58.”

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The case began on July 7, 2023, when Annette Flynn purchased 50/50 raffle tickets while tailgating before a Brewers game at American Family Field. One of those tickets was initially identified as the winning ticket worth $12,849. The Brewers Community Foundation later determined that Flynn failed to reach the designated claim location before the deadline and awarded the prize to an alternate winner. The Flynns challenged that determination, arguing that Annette rushed to claim the prize, was directed first to Guest Services, and that the Brewers’ timeline and video evidence should have been subjected to greater scrutiny.

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The litigation did not end the way the Flynns hoped. Milwaukee County Circuit Court Judge Carolina M. Stark dismissed the lawsuit without a trial, and the Wisconsin Court of Appeals later affirmed that decision. Neither court conducted a trial or made a factual finding regarding the exact moment Annette Flynn arrived at the claim location. Instead, the courts concluded that the raffle rules gave Brewers Community Foundation discretion to determine whether a claim was timely. The Flynns are now asking the Wisconsin Supreme Court to review the case, arguing that the dispute presents broader questions regarding judicial review of charitable raffle disputes and the use of “sole discretion” clauses when the organization administering the raffle also controls the evidence being challenged.

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The litigation history contains another notable detail. According to the Flynns, Brewers Community Foundation made a pre-discovery settlement offer that would have ended the case and required dismissal of the lawsuit. The offer was for $10,000 and included a confidentiality provision. The proposed settlement agreement defined the releasing parties as “the Flynns and their heirs, assigns, successors, agents, representatives, attorneys, and insurers.” The Flynns, who have ten children, objected to the breadth of the proposed release because it defined the releasing parties to include their heirs, assigns, and successors, even though none of their children were parties to the dispute.

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The Flynns declined the offer. “The issue for us was never just the money,” the Flynns said. “Had our goal been a payout, the case would have ended before discovery ever began. We wanted transparency, access to the evidence, and changes to the rules that affected every fan who purchased a raffle ticket.”

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The Brewers Community Foundation later changed its raffle rules. At the time of the Flynn dispute, winners were required to claim their prize before the end of the top of the seventh inning. Shortly before first pitch of the Brewers’ 2024 home opener, the Foundation revised its 50/50 raffle rules to extend the claim period until ballpark closing. The Foundation later adopted a policy giving winners 30 days to claim their prize. According to the Flynns, the revised 30-day rule could not be considered during the court proceedings because it was not part of the record before the courts.

The Flynns maintain that the evidence itself remains an important issue. The request for clarification was filed before the Court of Appeals issued its decision. Prior to that decision, they sought clarification regarding the status of the Brewers’ video exhibits after reviewing the appellate record and being unable to determine whether the actual video files had been transmitted as part of the record on appeal. The filing notes that the Brewers identified Exhibit 15 as “multiple video clips reflecting the events and locations of Mr. and Mrs. Flynn on July 7, 2023.”

Fox6 investigative reporter Jenna Sachs also spent months pursuing the story in 2024. In a January 11, 2024 email, Sachs requested an interview with Brewers Community Foundation officials and outlined concerns raised by Annette Flynn, including whether the shortened pitch-clock era made it difficult for older fans, disabled fans, parents with children, and fans seated farther from the claim location to claim a winning ticket. Months later, Sachs followed up after discovering the rule change. In an April 16, 2024 email, she noted that the claim period had been expanded and wrote that the story was not intended to be a “take-down” of the raffle program, but rather an examination of whether the previous timeframe was fair to fans. Sachs also wrote that there had been “some discussion between our organizations about this report” while she continued seeking interviews and information from Brewers representatives. Despite months of reporting efforts and communications with Brewers officials, Fox6 never aired a story on the dispute.

The newly disclosed communications provide a rare look at how Brewers officials responded to media scrutiny after Kenosha County Eye first brought public attention to the dispute. One communication references discussions between Brewers personnel and Fox6 representatives. Another shows Barnes expressing his hope that CBS58 would not air its story. Whether the Wisconsin Supreme Court agrees to hear the case remains unknown. As the legal battle enters its next chapter, however, the newly disclosed emails have created a separate debate involving media access, corporate influence, and how aggressively powerful organizations respond when faced with unfavorable publicity.

For the Flynns, the dispute is no longer just about a raffle ticket. It is about whether a powerful organization can control the rules, control the evidence, avoid a trial, and simultaneously seek to limit public scrutiny of the controversy.

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