A Kenosha couple who held the winning ticket in a Milwaukee Brewers 50/50 raffle has lost their legal bid to claim a $13,000 prize, after arriving at the redemption table just over a minute past the deadline. The Wisconsin Court of Appeals recently affirmed the circuit court’s ruling in favor of the Brewers Community Foundation. As first highlighted by BroBible and WBAY, Annette and Matt Flynn from Kenosha plan to take their case to the Wisconsin Supreme Court.
The incident occurred on July 7, 2023, during a Brewers game against the Cubs. Annette Flynn had purchased 10 tickets while tailgating before the game, and it is undisputed that she held the winning number when it was drawn midway through the sixth inning.
The rules at the time required the winner to redeem their ticket before the third out of the top of the seventh inning. Annette was seated in the upper deck in left field, with the scoreboard positioned behind her, so she did not see the initial announcement. After confirming the winning number on her phone, she began a frantic dash for the designated 50/50 table, during which an usher misdirected her to field level guest services instead of the correct table on the loge level concourse.
The foundation’s video evidence put Annette Flynn 66 seconds past the cutoff
According to the foundation’s timeline, the winning number was displayed on the scoreboard at approximately 8:51 PM on July 7, 2023. The critical deadline was recorded at approximately 9:12 PM. Video evidence showed Annette leaving her seating area at about 9:10 PM, arriving at the wrong desk at about 9:14 PM, and reaching the 50/50 table at approximately 9:15 PM. She was informed she had arrived 66 seconds late, and a new number was drawn.
The Flynns turned down a settlement offer and filed a small claims lawsuit seeking $10,000, the limit for such actions at the time. Milwaukee County Circuit Court Judge Carolina M. Stark granted summary judgment to the foundation, concluding that the official rules vested it with “sole discretion” to determine the winner and that this discretion had been reasonably exercised. Amid a broader wave of sports-related legal challenges, including a lawsuit filed against the NCAA by an NFL player arguing a sports organization profited from his likeness without adequate compensation, courts have consistently upheld the contractual authority of sports bodies to determine contest outcomes under their own rules.
On appeal, the Flynns argued genuine issues of material fact remained and challenged the foundation’s video evidence as inconsistent with their own recollections. They also attempted to argue that the foundation’s discretionary authority conflicted with Wisconsin law governing raffles, but the Court of Appeals found that argument was forfeited by failing to develop it before the circuit court.
The Court of Appeals upheld the circuit court’s decision. The court stated: “Under these rules, there is no genuine issue of material fact regarding whether the Flynns won the contest. They did not, because the Foundation concluded that Annette was late in presenting the winning ticket. The rules vest the Foundation with exclusive discretion to make that determination.” The court further noted that even if errors in the foundation’s video evidence could be shown, that would not create a genuine issue of material fact about whether the foundation had appropriately exercised its contractual discretion. The Flynns, as detailed by BroBible, have announced they plan to appeal to the Wisconsin Supreme Court.
Following the dispute, the Brewers have since updated their 50/50 raffle rules, giving winners a 30-day window to redeem a winning ticket. The inning-based deadline that cost the Flynns their prize no longer applies. Amid a run of notable court rulings this spring, a Love Is Blind: Argentina star was sentenced to 15 years in prison in a separate criminal proceeding, as courts across multiple jurisdictions handed down consequential decisions.
Published: May 27, 2026 06:00 am