Stanley Cup

How Rahm's Stanley Cup Bet Compares to Other Mayors' Wagers

More is on the line in Monday night’s Game 6 between the Blackhawks and the Tampa Bay Lightning than the Stanley Cup.

Mayor Rahm Emanuel and Tampa Mayor Bob Buckhorn also made bets on the outcome of the series, following the longstanding tradition of betting between mayors whose cities are fighting for the Cup.

Most of the bets are ridiculous, some are hilarious and others are cringe-worthy. So how does Mayor Emanuel’s bet stand up to those in the past?

Emanuel has bet 122 slices of Eli’s cheesecake (one for each year of the Stanley Cup), a case of craft beer from Slap Shot Brewing, a mustard fried catfish and peach cobbler from BJ’s Market and a Giordano’s deep-dish pizza.

Buckhorn countered with an offer of a case of Cigar City Invasion Pale Ale, 122 Ybor City Cuban sandwiches and Columbia’s original “1905 salad,” courtesy of the Columbia Restaurant.

While food and drink are usually the themes of the mayoral bet, sometimes the wagering goes further. Here’s a look back at the mayoral bets in the last four years of the Stanley Cup Final.


Last year, New York Mayor Bill de Blasio had the embarrassing task of singing “I Love L.A.” on “Jimmy Kimmel Live” after the Rangers lost to the Kings in the Stanley Cup Final. He also wore an “I (heart) L.A.” t-shirt while doing it. Mayor de Blasio isn’t particularly gifted when it comes to his singing voice, so Los Angeles Mayor Eric Garcetti got a good laugh out of the performance while watching from the “Jimmy Kimmel Live” studio.

It goes without saying, if New York had won the series, Garcetti would have had to sing “New York, New York” live.


Emanuel took his first hockey bet as mayor in 2013 when the Hawks played the Boston Bruins, and he did not take the task lightly. He bet at least twice as much as Boston Mayor Thomas Menino, but fortunately he didn’t have to send a single package.

That year, Emanuel bet corned beef sandwiches from Manny’s Cafeteria & Delicatessen, potato pancakes, six-packs of Green Line beer and root beer from Goose Island, Vosges Haut-Chocolat, Robinson’s BBQ sauce, El Milagro tortillas, Al’s #1 Italian Beef Sandwiches, Argo Tea, a touristy photo of Emanuel next to “the Bean,” tickets to the Steppenwolf Theatre Company, a “Menino 13” Blackhawks jersey, a Revolution Brewing Co. T-shirt, a bottle of Sriracha sauce former L.A. Mayor Antonio Villaraigosa gave a previous year and a tree for a schoolyard of the Boston mayor’s choice. Whew!

Menino, meanwhile, bet some of Boston’s best seafood, access to the Boston city website to post a video promoting tourism in Chicago, two tickets to the Huntington Theatre Company, two tickets to Theo Epstein’s “Hot Stove, Cool Music” concert in Boston and a tree to be planted in a Chicago schoolyard.


Unfortunately, no bet was made between Newark Mayor Cory Booker and Los Angeles Mayor Antonio Villaraigosa in 2012.


Boston made it to the Stanley Cup Final again in 2011 to face off against the Vancouver Canucks.

Mayor Menino offered a typical Boston gift that year: fresh lobsters, a variety of locally brewed beer, a donation to Vancouver Mayor Gregor Robertson’s charity of choice and the raising of the Vancouver Canucks flag on the City Hall plaza for one day.

In response, Mayor Robertson wagered wild British Columbia smoked salmon, locally brewed beer, a donation to Mayor Menino’s charity of choice and the raising of the Bruins flag in front of Vancouver’s City Hall for one day.

Robertson took it one step further, too, and later offered to wear a full-body yellow Lycra spandex suit worn by some sports fans. Menino, however, refused to offer the same.

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