The stakes will be somewhat lower — or at least will not involve live animals — on Sunday during Super Bowl LIII. Boston Mayor Marty Walsh has declared that his betting days are over, after a pair of brutal losses in 2014 forced him to sport a neon orange Denver Broncos jersey and fly the Montreal Canadiens’ flag above city hall. With that in mind, Boston City Council President Andrea Campbell has put up a relatively modest bet for the big game between the New England Patriots and Los Angeles Rams: Dunkin' coffee, razors from Gillette and some chocolate. If the Patriots win, Los Angeles City Council President Herb Wesson will be sending over a box of See’s Candies, a bag of Coffee Bean Coffee and a bottle of local wine. Both have pledged to wear the opposing team’s jersey at a council meeting if they lose.
The often eye-roll-inducing tradition of politicians placing friendly wagers before a big game is as old as the Super Bowl itself. A week before the first-ever AFL-NFL World Championship Game in 1967 (known later as Super Bowl I), Donald A. Tilleman, the mayor of Green Bay, Wis., sent a telegram to his counterpart in Kansas City, Mo., betting him a block of Wisconsin cheese that the Packers would win, and proposing that prime steaks would make for a good prize. The UPI reported that Kansas City Mayor Ilus W. Davis wired back immediately to accept the challenge, adding, “Hope you have the cheese packed." The Packers ultimately ended up beating the Chiefs, but Tilleman, who had been so confident that he didn’t bother to bring the cheese with him to the game, somehow managed to lose the steaks on his way home.
Since then, it has become practically obligatory for elected officials to enter into goofy, good-natured bets when their cities compete in major sporting events like the Super Bowl and the World Series. Even though critics deride the never-ending stunts as pointless and predictable, politicians apparently can’t resist the opportunity to show off their loyalty to local teams and tout their city’s regional specialties, all while demonstrating how hilarious and down-to-earth they are. As the Boston Globe noted in 2014, “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 airtime on the local news. What’s not to love?”
It’s hard to determine exactly how or when the custom started. As early as 1938, the mayors of New York and Chicago were betting on the outcome of the World Series, putting a box of cigars and a 500-pound dressed pig, respectively, on the line. By 1985, NFL legend John Madden had declared that he was sick of bets by mayors. Sports columnist Mike Downey agreed, writing in the Detroit Free Press that the contests had become “tiresome” and “ludicrous,” and that it was time to either give up or raise the stakes.
“What if the loser had to run naked through the winner’s business district during the next day’s rush hour?” he suggested. “Or let’s have the loser wear a T-shirt for 24 hours that reads: ‘I Am Mayor of the Worst City in the World.’”
Needless to say, neither scenario ended up happening. But rival cities' sports bets continued getting more and more ridiculous. The trend might have hit its apex in 1987, when Colorado’s governor shipped a 1,300-pound Angus steer to New Jersey after the New York Giants trounced the Broncos in Super Bowl XXI. (It was promptly donated to a farming museum.)
The tradition was firmly cemented in place by the ’90s, when Rudolph W. Giuliani became the mayor of New York. During his eight-year tenure as mayor, from 1994 to 2001, Giuliani “couldn’t wait to make bets with Democrats, Republicans, small-town mayors and big-city counterparts alike, just as long as a New York team was in the playoffs,” the New York Times would later recall. Even the Little League World Series merited placing a wager of H&H bagels and Nathan’s hot dogs. In one bet with a Texas mayor, Giuliani ended up winning a pair of cowboy boots that he subsequently concluded were good luck. He slipped them on for big games, he told the Times in 2011, and wore them to deliver stump speeches during his 2008 presidential campaign.
For years, most officials stuck to exchanging locally made products. A case of Napa Valley wine, 12 Dungeness crabs, and 12 loaves of sourdough bread from San Francisco. Buffalo steaks from Colorado. Spare ribs, Georgia peanuts and a case of Coca-Cola from Atlanta. A case of cereal, assorted nondairy products, and a crate of moisturizing lotion, bizarrely, from Buffalo. Two cases of barbecue sauce, 10 pecan pies, 10 gallons of chili, five gallons of hot sauce and 50 pounds of fajita meat from Dallas.
By 2008, it was no longer enough to merely offer up a single block of cheese. After the Packers lost in the NFC championship game to the Giants, New York Mayor Michael R. Bloomberg received a special delivery that contained 10 pounds of cheese spread, 20 aged strip steaks and three pounds of chocolate — plus a pair of cheese-wedge sunglasses for good measure.
A few weeks later, when the Giants faced the Patriots in the Super Bowl, Bloomberg teased a monstrous spread that would include 42 pastrami and corned beef sandwiches, five pizzas, Peter Luger steaks, a bushel of oysters and 42 pounds of rugelach. When the Patriots came up short, Boston Mayor Thomas M. Menino paid off the bet by delivering a truckload of clam chowder and Dunkin' coffee, which was donated to local homeless shelters and food banks. (As is common practice, the food came from corporate sponsors, not the city’s budget.)
On at least one occasion, when the Oakland A’s were set to play the San Francisco Giants in the 1989 World Series, mayoral betting led to hard feelings. Asked what the mayors of the two cities planned to bet, San Francisco Mayor Art Agnos replied that there wasn’t a single thing in Oakland that he wanted to win. The offhand remark enraged Oakland Mayor Lionel Wilson, who sent a wrathful note across the bay and then refused to return Agnos’s calls. “'I know what I’ll bet him,” Wilson told the Chicago Tribune. “Maybe I’ll have a plastic foot made he can put in his mouth.''
And there’s always the persistent question of whether politicians will follow through with their promises. In April 1997, more than two months after the Packers defeated the Patriots in that year’s Super Bowl, the Green Bay Press-Gazette reported that Mayor Paul Jadin still hadn’t collected the winnings from his bet with the mayor of Providence, R.I., Vincent A. “Buddy” Cianci Jr., who would later be sent to federal prison on racketeering charges. According to the terms of their wager, Cianci was supposed to have handed over 31 bottles of his own homemade marinara sauce and 31 pounds of tortellini. But Jadin told the paper that he didn’t feel it was his place to remind Cianci about the agreement.
When a Press-Gazette reporter called up Cianci to find out what had happened to the missing pasta, the Providence mayor claimed that he had brought it with him when he flew to New Orleans for the game and had planned to give it to Jadin in person. “I looked for him down there, but I couldn’t find him,” he said.
Instead, he told the paper, he had eaten 10 jars of the sauce himself, and given the rest to the Providence College men’s basketball team.