Friday evening, the Milwaukee Brewers defeated the Tampa Bay Rays 3-2 in the first game of the World Series. In the best-of-seven series, the ultimate victor must win four games. But there’s another friendly wager taking place beyond the ballpark.
St. Petersburg Mayor Ken Welch and Milwaukee Mayor Cavalier Johnson have announced a challenge that could leave the losing mayor wearing the opposing city’s team jersey around town.
There’s a communal benefit, though, beyond sheer bragging rights.
“We’re challenging our cities to turn all this baseball enthusiasm into something good for our neighbors,” Welch said in a social media announcement.
Both mayors are encouraging their cities to raise money for community organizations, with the mayor whose city raises less agreeing to wear the opposing team’s jersey and publicly congratulate the winning city.
For St. Pete, the beneficiary is St. Pete Free Clinic, one of Pinellas County’s largest providers of food assistance. The organization helps thousands of residents access nutritious food and healthcare. Milwaukee is supporting seven local homeless shelters through United Way.
“It’s a win-win in a lot of ways,” Welch told the Catalyst.
The two mayors share similar priorities, particularly when it comes to housing and addressing the everyday needs of residents.
“Mayor Welch and myself are both part of the United States Conference of Mayors,” Johnson told the Catalyst. “We decided to connect and put our staff together.”
Johnson said the challenge was about more than baseball or the prospect of wearing an opposing team’s jersey.
“What was most important to me and Mayor Welch is how we can make an impact off the field,” Johnson said. “Not just wearing opposing jerseys.”
Both mayors have emphasized housing as a priority, with Johnson declaring 2026 Milwaukee’s year of housing.
“What I’ve tried to tell people since I’ve been mayor: People are people, no matter where you are,” Johnson said. “All of us face the same challenges. It’s just a matter of scale.”
He pointed to the natural disasters St. Petersburg has faced and the significant rainfall Milwaukee has experienced this year – which caused many basements to flood – as examples of similar struggles.
“You can be a thousand miles away, but we face the same sort of challenges,” Johnson said.
“There’s a good synergy between his approach and mine,” Welch noted.
The mayors have also pledged to exchange gifts showcasing their respective cities. Welch’s collection includes contributions from St. Pete businesses, artists and cultural organizations, including Kahwa Coffee, the Dalí Museum, Green Bench Brewing Company and the St. Pete Youth Farm.
Johnson is no stranger to St. Petersburg. A big WWE fan, he has visited the city and relished its unique characteristics.
“My family really enjoyed being down in St. Petersburg,” Johnson said. “My wife and I spent so much time walking on the beach.”
Welch, in turn, has been a fan of Milwaukee craftsmanship long before the Rays faced the Brewers. He owns a Milwaukee-made, blacked-out Harley-Davidson Road King Special motorcycle, a longtime dream he fulfilled after taking office.
“The kids got a puppy, and I got a Harley,” Welch said.
If the Brewers win, Welch will ride his motorcycle around St. Pete wearing a Brewers jersey. Conversely, if the Rays win, Johnson will wear a Rays jersey, walk along the Milwaukee RiverWalk and light up a Milwaukee bridge in Rays colors.
Johnson, however, isn’t particularly worried about having to fulfill his end of the bargain.
“I feel very confident we will not have to follow through,” he said, while suggesting Welch might have gotten the better end of the deal: “He’s a fan of Milwaukee already with his love of Harley-Davidson motorcycles, so Welch has gotten off easy,” Johnson joked.
The World Series marks a moment of celebration for St. Petersburg after the city repaired Tropicana Field and brought the Rays back home.
“We’re going to the game on Monday. It’s an exciting time. The Trop will be rocking. It was a good game last night. The Brewers are the real deal, but I’m hoping we win this thing in the fifth game,” Welch said.
The mayor has emphasized the stadium’s importance as both a home for baseball and an economic driver for the city.
“I can’t imagine where we would be if we didn’t make the decision to fix the Trop,” he said.
The World Series gives both teams a chance to make history. Neither franchise has won a championship, adding more stakes and excitement to a matchup that has brought two cities together for a charitable cause.
Regardless of which team takes home the trophy, the mayors say their communities have an opportunity to come out ahead.
“On the field, the stakes are high, but between mayors, it’s a friendly wager,” Johnson said in the city’s announcement. “By incorporating a charitable element, everyone in both cities is a winner during this World Series.”
Welch is encouraging the public to donate to St. Pete Free Clinic at stpete.org/give. Residents can make monetary contributions or drop off needed items at 25 participating city facilities.
This is the first time the Rays and Brewers have faced each other in a World Series. Milwaukee previously reached the championship in 1982, losing to the St. Louis Cardinals in seven games. The Tampa Bay Rays made it in 2008, losing to the Philadelphia Phillies, and again in 2020, falling to the Los Angeles Dodgers.