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Annette and Matthew Flynn say missing out on a $13,000 jackpot during a 50/50 raffle at a Milwaukee Brewers home game has left them with new resolve — to face off with the ballclub in court.
Brewers Community Foundation Inc., the group that organizes the popular raffle that pops up during Brewers' home games, has maintained that Annette Flynn was too slow to pick up her winnings.
The Kenosha couple says that's not the case.
The Flynns say they're willing to continue to fight to get the money, despite a recent setback in their lawsuit to reclaim the money.
Here's what we know about the case and the couple behind it:
The Brewers Community Foundation is a nonprofit fund-raising arm of the Major League ballclub. It holds raffles during home games to help support more than 200 nonprofits throughout Wisconsin that focus on health, education, recreation and basic needs.
Tickets are $2 each.
The fan with the lucky ticket gets 50% of the net proceeds from the day's raffle ticket sales.
The winning number is drawn during the middle of the sixth inning, and the number is announced through the public address system and displayed on the scoreboard.
The rules say the winner has “until the end of the top of the 7th inning (or until the third out is recorded in the top of the inning)” to claim their prize at a 50/50 table on the loge level concourse of the stadium. If they don't do so in time, another number is drawn and another winner is selected.
Annette Flynn bought 10 tickets on July 7, 2023 . One of her tickets won.
Brewers officials say she arrived too late to pick up her winnings. She and her husband claim to have video evidence that backs up their story, but wasn't available in discovery during their small-claims case.
The Flynns filed a lawsuit against the Brewers in March 2025. They argued Annette Flynn arrived at the spot for winning ticket holders to claim their prize before the deadline, despite being momentarily misdirected there by an usher.
The case was heard by Circuit Court Judge Carolina Stark. She dismissed the case with prejudice, meaning the Flynns cannot bring the same suit back to court, on Dec. 22.
The couple filed an appeal on Jan. 26.
A state appeals court sided with Stark's ruling on May 19. In expressing their disappointment with the ruling, the Flynns publicly announced they are considering taking the case to the state Supreme Court.
The couple lives in Kenosha and run Sophisticatering, a catering business.
Annette Flynn ran twice to serve on the Kenosha County Board of Supervisors, in 2024 and 2026.
The 2024 race between her and incumbent Supervisor Jeffrey Gentz ended with Gentz winning the Dist. 3 seat by just nine votes after a recount.
In the April 2026 election, she lost to Riki Tagliapietra by 32 votes.
Chris Ramirez covers courts for the Milwaukee Journal Sentinel. He can be reached at [email protected].
This article originally appeared on Milwaukee Journal Sentinel: Kenosha couple sued Brewers over 50/50 raffle winnings: What to know
Continue reading...
Brewers Community Foundation Inc., the group that organizes the popular raffle that pops up during Brewers' home games, has maintained that Annette Flynn was too slow to pick up her winnings.
The Kenosha couple says that's not the case.
The Flynns say they're willing to continue to fight to get the money, despite a recent setback in their lawsuit to reclaim the money.
Here's what we know about the case and the couple behind it:
What is the Brewers' 50/50 raffle?
The Brewers Community Foundation is a nonprofit fund-raising arm of the Major League ballclub. It holds raffles during home games to help support more than 200 nonprofits throughout Wisconsin that focus on health, education, recreation and basic needs.
Tickets are $2 each.
The fan with the lucky ticket gets 50% of the net proceeds from the day's raffle ticket sales.
How does the 50/50 raffle work?
The winning number is drawn during the middle of the sixth inning, and the number is announced through the public address system and displayed on the scoreboard.
The rules say the winner has “until the end of the top of the 7th inning (or until the third out is recorded in the top of the inning)” to claim their prize at a 50/50 table on the loge level concourse of the stadium. If they don't do so in time, another number is drawn and another winner is selected.
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Why are Annette and Matthew Flynn suing the Brewers?
Annette Flynn bought 10 tickets on July 7, 2023 . One of her tickets won.
Brewers officials say she arrived too late to pick up her winnings. She and her husband claim to have video evidence that backs up their story, but wasn't available in discovery during their small-claims case.
Here's how the case has unfolded in the courts
The Flynns filed a lawsuit against the Brewers in March 2025. They argued Annette Flynn arrived at the spot for winning ticket holders to claim their prize before the deadline, despite being momentarily misdirected there by an usher.
The case was heard by Circuit Court Judge Carolina Stark. She dismissed the case with prejudice, meaning the Flynns cannot bring the same suit back to court, on Dec. 22.
The couple filed an appeal on Jan. 26.
A state appeals court sided with Stark's ruling on May 19. In expressing their disappointment with the ruling, the Flynns publicly announced they are considering taking the case to the state Supreme Court.
Who are Annette and Matthew Flynn?
The couple lives in Kenosha and run Sophisticatering, a catering business.
Annette Flynn ran twice to serve on the Kenosha County Board of Supervisors, in 2024 and 2026.
The 2024 race between her and incumbent Supervisor Jeffrey Gentz ended with Gentz winning the Dist. 3 seat by just nine votes after a recount.
In the April 2026 election, she lost to Riki Tagliapietra by 32 votes.
Chris Ramirez covers courts for the Milwaukee Journal Sentinel. He can be reached at [email protected].
This article originally appeared on Milwaukee Journal Sentinel: Kenosha couple sued Brewers over 50/50 raffle winnings: What to know
Continue reading...
