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Memorial principal Oldenberg wins $131,773 raffle at Brewers World Series game

Le
Leader-Telegram, Eau Claire, Wis.
By Leader-Telegram, Eau Claire, Wis.
10/27/2026, 1:52:00 AM
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EXECUTIVE SUMMARY

It was an opportunity die-hard Milwaukee Brewers fan Dave Oldenberg couldn’t pass up. And it provided him with a memory of a lifetime. The Eau Claire Memorial High School principal secured tickets to attend Game 2 of the World Series on Saturday, the first time the Brewers had reached the World Series since 1982. Oldenberg was still in high school back then. Now 44 years later he watched as ...

Key Takeaways

  • Memorial principal Oldenberg wins $131,773 raffle at Brewers World Series game.
  • It was an opportunity die-hard Milwaukee Brewers fan Dave Oldenberg couldn’t pass up.
  • And it provided him with a memory of a lifetime.

It was an opportunity die-hard Milwaukee Brewers fan Dave Oldenberg couldn’t pass up. And it provided him with a memory of a lifetime.The Eau Claire Memorial High School principal secured tickets to attend Game 2 of the World Series on Saturday, the first time the Brewers had reached the World Series since 1982.Oldenberg was still in high school back then. Now 44 years later he watched as the Brewers came back for a thrilling 5-4 win over the Tampa Bay Rays at American Family Field to take a 2-0 series lead.“It was insane,” Oldenberg said. “I have never been to an event that electric in my life.”Leaving Milwaukee, Oldenberg said the memories and emotions from the night will stick with him forever.Oldenberg, however, didn’t expect to leave Saturday with a little extra to celebrate, as he won $131,773 from the Brewers Community Foundation 50/50 Raffle.“I’m like ‘This is a once-in-a-lifetime opportunity,’” Oldenberg said. “Clearly, the return on the investment for the tickets has paid off with a great game, and then this goofy thing.“It was completely dumb luck. It’s like being struck by lightning. Just right place, right time.”Like any Brewers fan, Oldenberg has waited and waited for Milwaukee to end its World Series drought, which dates back to the team’s founding in 1970 and it’s seven-game loss to the St. Louis Cardinals in 1982.When the Brewers clinched their trip to the Fall Classic with a sweep of the back-to-back defending champion Los Angeles Dodgers, Oldenberg wanted to be a part of it.“I bought the tickets last week,” Oldenberg said. “I went with several friends of mine.”The $2,400 price tag didn’t scare Oldenberg away from the chance to see his team potentially make history.Oldenberg’s history with the Brewers also involves a tradition. Every game he attends, he throws $20 in the 50/50 raffle.“The 50/50 folks were out in the tailgate,” Oldenberg said. “It was one of the very first things I did.”Participants have a chance at winning 50% of the proceeds from the tickets, with the rest going to the Brewers Community Foundation.With it being the World Series, that pool skyrocketed to $131,773, the highest prize pool ever awarded in the stadium’s history, breaking the previous record of $112,410 set during Game 1 the night before.In the sixth inning, the winning digits were announced.“I took a picture of the scoreboard so I could just have the number,” Oldenberg said. “I said, ‘I’ll check when I get a chance.’ So, middle of the seventh inning, I checked, and I’m like, ‘Well, this can’t be right.’”Oldenberg glanced down at his 10 tickets and couldn’t believe his numbers, 6015455, matched those on the screen.Oldenberg checked with a security guard, who saw Oldenberg’s ticket was correct and directed him to guest services who also confirmed Oldenberg as the winner.“Chaos ensued,” Oldenberg said. “People (were) coming up, shaking my hand, hugging me and trying to buy me beers. So, that’s when it became real.”Adding to the elation was when the Brewers tied and took the lead for good Saturday.“In the middle of signing all the paperwork, (Brewers outfielder) Sal Frelick hit the (game-tying) home run,” Oldenberg recalled. “I’m like, ‘You’ve got to be kidding me right?’”The foundation posted a photo of Oldenberg with his winning check on its social media, giving way to thousands of congratulatory messages being sent his way since Saturday.“The reaction to it, the kind comments and congratulations have been overwhelming,” Oldenberg said.Now suddenly $130,000 richer, Oldenberg said he hasn’t thought about where to use his winnings. Well, except for two possibilities.“If there’s a game six or seven in Milwaukee, I will be going,” Oldenberg said. “I can buy any seat I want now.”It’s the cherry on top of an already celebratory school year for Oldenberg, who recently announced he would be retiring next June after 20 years in Eau Claire and 32 years in education.“You know when it’s time to turn the page,” Oldenberg said. “I love Memorial. I love everything about Memorial High School. You know it’s time for the next chapter of life.”Wherever that chapter brings him, Oldenberg is thankful.“I joke with people,” Oldenberg said. “The things I really care about in life are my two daughters, Diet Pepsi; I drink lots of Diet Pepsi. I care about the Milwaukee Brewers and Memorial High School.“By far and away, being principal at Memorial is the best thing that anybody could ask for, and then you put this on top of it.”

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