The Long, Dumb History of Mayors Making Sports Bets

Boston Mayor Marty Walsh and Montreal Mayor Denis Coderre make their bet on the Bruins-Canadiens series.
Boston Mayor Marty Walsh and Montreal Mayor Denis Coderre make their bet on the Bruins-Canadiens series.
City of Boston Mayor’s office

With the Boston Bruins and Montreal Canadiens facing off for the 34th playoff series in their history, mayors Marty Walsh and Denis Coderre got into the sports bet game Thursday. As mayoral bets go, this one was tame. The losing mayor must tour the winning mayor’s city. The winning team’s flag will fly outside the loser’s city hall.

Mayors love this stuff. They get associated with a winning local team, there’s almost never a political backlash, they’re convinced it’s wicked funny, and they get free air time on the local news. What’s not to love?

But placing the perfectly vapid sports bet is more art than science. Cash wagers are out of the question, and while we’d all love a “How I Met Your Mother” style slap bet, no mayor is going to go for that. In the end, they usually stick to either a trade of local delicacies and goods or some sort of embarrassment.

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Every once in a while, however, mayors think outside the box and get an actually entertaining bet off the ground. Here are a few of the best (and worst) mayoral bets over the years.

2004 World Series

The teams: The Boston Red Sox defeated the St. Louis Cardinals

The mayors: Boston’s Tom Menino and St. Louis’s Francis Slay

The stakes: Tasty(?) local food

Local delicacies are a tried and true wager between cities, but not every city has the same quality stuff. In 2004, Mayor Menino put together a package of goods against a similar basket from St. Louis Mayor Francis Slay. Menino included cases of Sam Adams and Harpoon, a clam bake dinner from Yankee Lobster, and more.

Slay responded in kind with Budweiser, toasted ravioli, chocolate, and the swag he won in previous bets. It was like a sad bachelor Happy Meal. Maybe that’s why Slay didn’t want to wager on last year’s Sox-Cards World Series; He was too embarrassed from the last time around.

Super Bowl XLV (2011)

The teams: The Green Bay Packers defeated the Pittsburgh Steelers

The mayors: Green Bay’s Jim Schmitt and Pittsburgh’s Luke Ravenstahl

The stakes: Manual labor

Sports website The Score called this the stupidest Super Bowl bet in NFL history, and it’s hard to disagree. The mayors decided they’d shovel the walkway of a rival team’s fan in their city. With Green Bay’s win, that meant Ravenstahl had to shovel a Piuttsburgh church’s walkway (Green Bay coach Mike McCarthy’s parents attend the church).

The Post-Gazette was the big winner here, capturing video of Pittsburgh’s mayor complaining about the bet while wearing a Packers shirt.

“I was hoping and had my fingers crossed that we wouldn’t have to do this,” said Ravenstahl. About shoveling a walkway. For a church.

Super Bowl XVII (1983)

The teams: The Washington Redskins defeated the Miami Dolphins

The mayors: We’re cheating a little here, because the bet was so good. This was between Virginia Gov. Charles Robb and Florida Gov. Bob Graham

The stakes: Live animals

In perhaps the most memorable political sports bets of all time, Robb put up a live pig named Josephine against Graham’s wager of 3,000 bees. According to Mental Floss, the pig was a reference to Washington’s non-official “Hogs” nickname, and the bees referred to Miami’s “Killer B’s” defense.

2013 Florida high schools’ rivalry game

The teams: The Zephrillis High Bulldogs defeated the Pasco High Pirates (Pasco High is in Dade City, Florida)

The mayors: Zephrillis’s Danny Burgess and Dade City’s Camille Hernandez

The stakes: Embarrassment

You’ve never heard of the teams, the rivalry, or even the towns, but as embarrassment wagers go, this was a good one. The losing mayor had to wear the mascot costume of the winning team, according to The Tampa Tribune. Burgess donned the giant, cartoonish head of the Pasco Pirate during his next city council meeting.

2010 NBA Championship

The teams: The Los Angeles Lakers defeated the Boston Celtics

The mayors: Menino and Los Angeles Mayor Antonio Villaraigosa

The stakes: Celebrities

Listen, we all love Matt Damon and we, you know, tolerate Ben Affleck, but putting the pair up against Jack freaking Nicholson? Even at two celebs to one, Los Angeles wins on the stakes alone. The winner got the loser’s star(s) to film a commercial touting tourism in the winning city.

1989 World Series

The teams: The Oakland A’s defeated the San Francisco Giants

The mayors Oakland’s Lionel Wilson and San Fran’s Art Agnos

The stakes: Unbridled fury

You could really write a book about the 1989 World Series (people have), which featured a devastating earthquake, the Bash Brothers Mark McGwire and Jose Canseco, and the most bitter mayor feud in sports betting history.

It all started when Agnos told a local news station that he wasn’t going to make a wager because there was nothing in Oakland he would ever want, according to The Atlantic Cities. An apoplectic Wilson then fired off an angry letter to Agnos. After that, he stopped returning Agnos’s calls. Wilson later said “I know what I’ll bet him. Maybe I’ll have a plastic foot made he can put in his mouth,” according to the Chicago Tribune.