MILWAUKEE, Wis. — The Wisconsin Supreme Court has rejected the final appeal of Matt and Annette Flynn, the Kenosha couple who spent more than three years fighting the Milwaukee Brewers Community Foundation over a $12,849 winning 50/50 raffle ticket that they were never allowed to cash. The state’s highest court denied the couple’s petition for review on Wednesday, October 14, 2026, without providing an explanation, bringing their lengthy legal battle to an end. However, the Flynns are not backing down from their position that critical evidence concerning the disputed raffle was never fully examined by a judge or jury. The couple has now provided Kenosha County Eye with additional documentation showing that they specifically requested information about when the winning number appeared on the Brewers’ website and sought additional surveillance footage that they believe could have helped establish whether Annette reached the prize-claim location before the deadline. The dispute has also raised questions about behind-the-scenes communications between senior Brewers officials and Milwaukee television stations, including an email in which a Brewers vice president explicitly expressed his hope that a news report about the controversy would not air.
The Supreme Court’s order, issued in case 2026AP233, denied the petition without costs. The decision leaves intact an earlier ruling by Milwaukee County Circuit Court Judge Carolina M. Stark, who dismissed the Flynns’ lawsuit without a trial, and a subsequent Wisconsin Court of Appeals decision affirming that dismissal. Neither court conducted a trial to determine the precise moment Annette Flynn arrived at the raffle claim location. Instead, the lower courts concluded that the raffle rules gave the Brewers Community Foundation discretion to determine whether a winning ticket had been claimed on time. The Supreme Court’s denial does not constitute a new factual determination that Annette was late.
The dispute dates back to July 7, 2023, when Annette Flynn purchased $20 worth of 50/50 raffle tickets while tailgating before a Milwaukee Brewers game at American Family Field. One of those tickets, numbered 5632027, was drawn as the winner of a $12,849 prize. After discovering she had won, Annette sprinted toward the claim location while her husband, Matt, followed behind at a slower pace. Annette initially went to Guest Services after receiving directions from stadium personnel, only to be redirected to another location. By the time she reached the designated 50/50 raffle desk, employees informed her that she was too late and that another winning number had been selected.
The Flynns have consistently disputed the Brewers Community Foundation’s timeline. They maintain that Annette reached Guest Services before the end of the top of the seventh inning, the deadline established under the raffle rules at the time. Matt has also maintained that he personally witnessed the final out and believes Annette was already at Guest Services before that occurred. The couple argues that the surveillance footage, including their movements relative to one another, raises questions about the timestamps used to support the Foundation’s determination.
New Documents Reveal Dispute Over Website Posting Time
One of the central issues raised in the newly provided documentation concerns the exact time the winning raffle number was posted on the Brewers Community Foundation’s website. The Flynns say this information was particularly important because Annette could not see the winning number displayed inside the stadium from her seating location and instead checked the Foundation’s website on her phone. Knowing precisely when the number appeared online could help establish how much time Annette actually had to reach the claim location after discovering she possessed the winning ticket.
In their second set of discovery requests, the Flynns specifically asked the Foundation to identify the time of day that the winning number was posted online on July 7, 2023. According to the discovery documentation provided to KCE, the Foundation objected to the request on several grounds, including relevance, timing and proportionality. The Foundation also characterized the request as redundant or cumulative, referred to evidence already produced, and declined to provide an additional response or documents. The exact website-posting time was not supplied in the materials described by the Flynns.
On September 29, 2025, the Flynns filed a motion to compel discovery responses, specifically identifying the unanswered website-posting question as an issue they wanted the court to address. The couple argued that the information could be compared against surveillance footage showing Annette checking her phone and subsequently leaving her seating area to claim the prize. However, on December 22, 2025, Judge Stark granted summary judgment in favor of the Brewers Community Foundation and dismissed the lawsuit with prejudice. The written summary judgment order did not separately decide the motion to compel, according to the Flynns’ documentation.
The Flynns subsequently sought reconsideration, but Judge Stark denied that request on January 15, 2026. In her order, Stark stated that the court was “well aware of the discovery issue cited in the motion” when it granted summary judgment. The ruling establishes that the court knew about the discovery dispute, although the Flynns maintain that the underlying information they sought was never provided. Their latest documentation does not establish what the missing website timestamp would have shown, but it does establish that the couple requested the information and challenged the Foundation’s refusal to provide it.
Surveillance Footage Raises Another Unanswered Question
The second major issue concerns the movements of Matt and Annette Flynn during the final moments of the seventh-inning deadline. According to the couple, surveillance footage produced by the Brewers Community Foundation follows virtually Annette’s entire route toward the claim location, with the exception of her movements along ramps leading to the lower-level concourse. The Flynns maintain that the footage consistently shows Matt following behind Annette and that none of the footage provided to them shows Matt passing her.
That distinction matters because the Flynns contend that the Foundation relied upon selected, time-stamped surveillance evidence to establish where Annette was when the final out occurred. Their discovery documentation specifically references approximately 9:12:34 p.m., when the Foundation’s evidence purportedly placed Annette near the Stadium Bar while Matt was elsewhere watching the final out. The couple questions how that timeline could be reconciled with footage they say shows Annette remaining ahead of Matt throughout the recorded portions of their movements.
During discovery, the Flynns requested additional timestamped surveillance footage depicting both of them traveling from Section 234 toward the raffle claim location. Requests numbered 7 through 13 sought footage of specific portions of Matt’s route, including concourse areas and his movements toward the claim desk. According to the documentation, the Brewers Community Foundation objected to those requests, including on the grounds that Matt’s location at a particular time was not relevant to whether Annette had claimed her prize within the required period.
The Foundation did produce surveillance clips during discovery and identified video evidence it intended to present if the case proceeded to trial. However, because the lawsuit was dismissed on summary judgment, no trial occurred and no judge or jury evaluated the complete surveillance sequence in a trial setting. The Flynns say the footage should be examined as a continuous sequence rather than relying exclusively on individual images and timestamps. The documents provided to KCE do not independently establish that the Foundation’s timeline was incorrect, but they demonstrate why the couple continues to question it.
In a statement issued following the Supreme Court’s decision, the Flynns described their concern as a “sword and shield” problem. They contend that the Foundation used selected surveillance evidence to support its version of events while the broader sequence they wanted examined never received a full factual hearing. The couple has made clear that they are not asking the public simply to accept their account over the Foundation’s. Instead, they want the evidence made available so others can examine the competing timelines.
Supreme Court Decision Ends Litigation, But Not the Questions
The Supreme Court’s October 14 order is brief and does not explain why the justices declined review. The decision ends the couple’s attempt to obtain further review through Wisconsin’s appellate courts, leaving the circuit court’s dismissal in place. It also means the Flynns will not receive the $12,849 raffle prize through this lawsuit, despite having pursued the dispute through the circuit court, the Court of Appeals and the state’s highest court.
The Flynns previously told KCE that the Brewers Community Foundation offered them $10,000 to settle the case before discovery was completed. The proposed agreement included confidentiality language and would have required dismissal of the lawsuit. The couple, who have ten children, objected in part to the breadth of the proposed release, which defined the releasing parties to include their heirs, assigns and successors. They declined the settlement, maintaining that their objective was to obtain evidence and answers about the handling of the raffle rather than accept a confidential resolution.
The Brewers Community Foundation also changed its raffle procedures after the original dispute. At the time of the July 2023 game, winning ticket holders had until the end of the top of the seventh inning to claim their prizes. Shortly before the first pitch of the Brewers’ 2024 home opener, the Foundation revised its website to extend the claim period until the ballpark closed. The Foundation subsequently adopted a policy allowing winners 30 days after the drawing to claim their prizes. The Flynns say those changes underscore their longstanding concerns about whether the original deadline provided fans enough time to navigate the stadium, particularly elderly fans and people with disabilities.
Flynns Seek Greater Transparency In Brewers Raffle Operations
The couple’s concerns have also expanded beyond their own winning ticket. In correspondence dated October 15, 2026, Annette Flynn sought additional clarification from John Dillett of the Wisconsin Division of Gaming regarding public access to raffle drawing recordings. Her letter referenced a July 8, 2026 response from the Division that, according to Flynn, determined the Foundation’s previous drawings had not been conducted “in public” as required by Wisconsin law. The Division reportedly accepted a procedure allowing individuals to review recordings of particular drawings in a designated Foundation office area, provided they possessed a game ticket for the corresponding drawing.
Annette questioned why access to recordings of drawings required to be conducted publicly would be limited to individuals possessing tickets for the particular games. She also asked whether journalists, non-attendees and other members of the public could independently review the recordings, whether the Division could obtain copies in response to complaints, and how long the recordings must be retained. The Flynns indicated that they wanted to review certain drawings listed as claimed for which they had not located corresponding winner photographs on the Foundation’s Facebook page. They expressly acknowledged that the absence of photographs does not itself establish any irregularity.
The Flynns also want to know how much the Brewers Community Foundation spent defending the litigation over a prize worth approximately $13,000. Their statement questions why the dispute continued for more than three years when, in their view, additional objective evidence could have helped resolve the underlying disagreement. The Foundation had the right to defend its position in court, and the courts ultimately ruled in its favor. The Flynns nevertheless believe the public should be able to examine the evidence underlying a charitable raffle dispute, even after the legal proceedings have ended.
Brewers Vice President Privately Urged CBS58 General Manager Not To Air Story
The controversy also raised questions about the Brewers’ behind-the-scenes efforts to discourage unfavorable news coverage. On May 20, 2025, Brewers Senior Vice President of Communications and Affiliate Operations Tyler Barnes sent an email directly to Anne Brown, Vice President and General Manager of CBS58, rather than responding to the station employee who had requested comment about the Flynn lawsuit. Barnes wrote that the Flynns continued to pursue media attention despite what he characterized as evidence supporting the Brewers’ position. He then made his preference unmistakably clear: “Our hope is that the story does not air — it’s just not productive to discuss through public channels.”
Barnes also acknowledged that his inclination was not to respond to the original CBS58 employee, but that the Brewers would provide a statement “out of respect for you and others at CBS-58.” Although CBS58 ultimately aired its report, the correspondence raises questions about why a senior Brewers executive chose to communicate directly with the station’s general manager while expressing his desire that the story never reach viewers. The email documents Barnes’ preference and his communication with station leadership, although it does not establish that CBS58 changed any editorial decision because of it.
Kenosha County Eye was the first news outlet to report extensively on the Flynns’ dispute, which subsequently attracted attention from Milwaukee television stations and other media organizations. Fox6 investigative reporter Jenna Sachs spent months pursuing the story in 2024, requesting interviews with Brewers representatives, information about the raffle rules and access to surveillance footage. In an April 16, 2024 email, Sachs acknowledged there had been “some discussion between our organizations about this report.” Despite those efforts, Fox6 never aired its investigation. The correspondence does not establish that the Brewers caused Fox6 to abandon the story, but it provides additional context about communications taking place while coverage was being considered.
For Matt and Annette Flynn, the Supreme Court’s denial marks the end of their legal battle, but not the end of their questions. They maintain that the most important issues remain the exact time the winning number appeared online and the locations of both spouses when the final out occurred. The couple says the evidence should speak for itself, rather than requiring fans to choose between competing accounts of what happened that night. As they put it in their statement following the Supreme Court decision: “A screenshot captures a moment. A video shows what happened before and after that moment.”
2 Responses
They were initially offered $10k, but didn’t want to sign the NDA. So they’re looking for the story more than the money? A big organization isn’t going to go along with a shakedown for more money… which would be the only reason for not signing.
Should’ve taken the money and let it go.
Thank you, Kevin, for your continued interest in our story and for taking the time to review the documents and evidence. Annette and I truly appreciate you following this case and giving readers the opportunity to consider the facts and unanswered questions for themselves.