Even if you’re not a rabid baseball fan, you’d be hard-pressed not to envy Rick Schlesinger’s (’83) office. A panel of windowpanes offers a breathtaking vista of the right-field grass in American Family Field, the home stadium of the Milwaukee Brewers.
It’s a view Schlesinger, who graduated from UW–Madison with degrees in history and political science, has savored for the last 21 years since he was hired to oversee the Brewers’ business operations in 2003.
Schlesinger’s list of responsibilities is almost as long as a Major League Baseball season — ticket sales, sponsorships, broadcasting, media relations, stadium operations, community relations, legal, business analytics, IT, finance and human resources.
He’s faced with an equally long list of challenges, such as evolving to meet the changing needs of Brewers fans, incorporating new technology, generating new sources of revenue and finding ways to keep fan engagement high in a crowded and unstable media landscape.
“I like to say that we compete with sleep,” says Schlesinger, grinning. “We’re trying to be all things all the time — not just during games and not just during the baseball season. We want to engage with our audience all the time with as many different touch points as they want to allow.”
It isn’t always easy. The Brewers have had a remarkable run of on-field success in the last several years. They’ve made the playoffs in six of the last seven years, including a 2018 run to the National League Championship Series. But player payroll is routinely dwarfed by big-city rivals like the Los Angeles Dodgers and the Atlanta Braves. Major League Baseball is assuming the production and distribution of Brewers games starting next season, creating uncertainty in the Brewers’ local and regional media landscape.
“Baseball’s economic structure is so different from the other leagues,” Schlesinger says. “You have to deal with the realities of the economics of the sport you’re in. I don’t think we obsess about it or worry too much about it. We just try to make the best decisions.”
Schlesinger started his career on a common path for history and political science majors — he went to law school. He says that his first years as a lawyer in Los Angeles were brutal and uninspiring. Then, like the star athletes who win the World Series, he announced he was going to Disney World.
Or, rather, to Walt Disney Pictures and Television, where he handled production, development and finance. The House of Mouse already owned one professional sports team (the National Hockey League’s Mighty Ducks) when Schlesinger arrived, and then they added Major League Baseball’s then-Anaheim Angels to the fold. They asked Schlesinger to become general counsel for both teams. Schlesinger, who has always loved baseball — his father was offered a contract to play for the Chicago Cubs before enlisting and fighting in World War II — pounced on the opportunity. He handled both teams for five years before being recruited to Milwaukee.
Like most MLB squads, the Brewers have invested heavily in data and analytics. On the player side, that informs decisions on when to pull the starting pitcher. On the business side, it’s about figuring out who the fans are and how best to reach and engage them. For Schlesinger, data’s critical, but it can never fully trump baseball’s 12 decades of tradition.
“We’re trying to deliver the experience the individual fans want,” says Schlesinger. “There are 40,000 potential fans at every game, and there are 40,000 potential ways to reach them.”
Schlesinger likes to cite former MLB Commissioner Allan “Bud” Selig (’56) — an L&S alum who teaches an annual course about baseball and history — for describing baseball as a “social institution.” As a Wisconsinite, the sentiment resonates with Schlesinger, who takes the community relations piece of his gig very seriously.
We’re a regional team. It’s not just Milwaukee — it’s the entire state of Wisconsin.
“We’re a regional team,” he says. “It’s not just Milwaukee — it’s the entire state of Wisconsin.”
Schlesinger has a World Series ring from his time with the Angels — game seven of that series was played on Schlesinger’s birthday — but he’d love to win another with the Brewers. The Brewers’ win over the Chicago Cubs, their heated rival, in game 163 at Wrigley Field in 2018 to win the division and advance to the playoffs stands as his career high point — as both an executive and a baseball fan.
“Wrigley Field was 70% Brewers fans,” he chuckles. “And that made it even more special.”
When he’s not immersed in baseball biz, Schlesinger spends most of his time reading history books, usually on his iPhone. He’s partial to 19th-century U.S. history and 1930s-era European history, with particular interest in the Civil War and Winston Churchill, respectively.
“I’m never away from history, because I’ve got my iPhone in my hand all the time,” he says. “If I’m looking at box scores or our game broadcasts on the road, I’m also looking at history books.”
Schlesinger acknowledges that making decisions about the Brewers’ broadcast options is a far cry from making decisions about world events, but the lessons history has taught him about the value of leadership resonate sharply in his day-to-day.
“To be a good leader, a good role model, you have to be a good listener and juggle different viewpoints,” he says.
Schlesinger plans to end his career with the Brewers and remain in the Milwaukee area once he leaves his spectacular office view behind. He thinks often about following his friend Selig into teaching — combining his love of history and baseball.
“If I could reinvent myself, I’d go back and take history courses for the rest of my days,” Schlesinger says.
