You are here

The 11 Cleverest Sports Playoff Bets

When cities put their pride on the line, it means a lot of wagers on pizza, pastrami sandwiches, and even artwork.
The 11 Cleverest Sports Playoff Bets

What’s better than playoff sports?

Entire cities coalesce in support of a common team. The buzz is different, the air is pure and the excitement is palpable. Fans get closer to the individual players, the team, and their fellow fans.

The 10 Best NBA Playoffs Performances of All Time >>>

Total strangers are united by their devotion to a single goal. Everyone, even the fair-weather fan, wants in on the action. And when fair-weather fans start multiplying in numbers, politicians are the last to follow, figuring they can endear themselves to voters in perhaps the easiest of ways: watching sports. That’s why, when playoff time comes around, politicians lavish their attention on the sports world. And what better way to demonstrate your interest with a good old friendly wager? It shows you’re backing the team and that you’re one with the people. Genius.

The 15 Greatest Underdog Sports Stories of All Time >>>

For decades, politicians have been making cordial, meaningless bets on playoff series with their counterparts in other cities. It started with signature foods—pastrami sandwiches in New York, clam chowder from Boston. Since then, it's expanded from the realm of food and politics into more sophisticated realms, like art and late-night comedy.

Here are 11 of our favorites:

8 Quirky Days With the Stanley Cup >>> 

If only Pete Carroll had just given Marshawn Lynch the ball, the Seattle Seahawks probably would have been Super Bowl champs. That’s how most Americans—and certainly most Seahawks fans—feel to this day. And the loss must have been especially difficult for the folks at the Seattle Art Museum, who, because of that play, lost one of their prized paintings: Albert Bierstadt’s Puget Sound on the Pacific Coast (1870).

Before the game, the Seattle Art Museum made a high-stakes bet with the Clark Art Institute in Williamstown, Massachusetts: winner got one of the loser’s paintings on a three-month loan.

This bet, the first of its kind, helped connect the two cities and set the framework for Pittsburgh and San Jose’s 2016 Stanley Cup Finals bet, which also included some famous art.

10 Biggest Disappointments in Super Bowl History >>>


Before the 2014 Eastern Conference Stanley Cup Finals, Jimmy Fallon reached out to the Montreal Canadiens via Twitter in support of his hometown New York Rangers. Fallon proposed that if the Rangers won, the Canadiens would have to change their Twitter account photo to a picture of Fallon, and that the Canadiens' mascot would have to travel to ten Montreal landmarks wearing a Rangers jersey. If the Canadiens won, Fallon would have had to wear a Canadiens jersey during one of his monologues. The result:

The 17 Toughest, Gnarliest, and Most Terrifying Hockey Players to Ever Throw a Punch >>>

The late 1990s was a productive time to be a Yankees fan with a gambling streak, and that was doubly so for then-New York City Mayor Rudy Giuliani, who made bets on almost every Yankee playoff series. And that meant bad news for Arlington Mayor Elzie Odom.

The rivalry started with the 1996 ALCS between the Yankees and the Texas Rangers. The Yankees won the series 3-1 and Giuliani, in turn, won a pair of cowboy boots. In 1998, the Yankees and the Rangers faced off once again. Unsurprisingly, Giuliani went back to the well (if only we all had the 114-win '98 Yankees in our corner) and made another bet with Odom. The Yankees swept the series and Giuliani came away with a ten-gallon hat to match his cowboy boots.

Yankees Recreate Epic Scene from The Sandlot >>>

Before the 2011 Super Bowl, Pittsburgh Mayor Luke Ravenstahl and Green Bay Mayor Jim Schmitt bet that the loser would have to find an opposing team’s fan and—in the middle of February—shovel their driveway.

Green Bay, of course, emerged triumphant. So who did Schmitt pick for Ravenstahl to help out? That of Packers head coach Mike McCarthy, who, ironically, is a Pittsburgh native. Schmitt asked Ravenstahl if he would clean the front steps of the McCarthys' church, and Ravenstahl made good.

 James Harrison Executes a Pushup You Couldn't Do >>>

Super Bowl XLII was perhaps the greatest football game of all time. Eli Manning, David Tyree, Tom Brady, Michael Strahan—17-14 Giants win. You already knew that.

What you probably did not know was that before the game, NYC Mayor Michael Bloomberg and Boston Mayor Thomas M. Menino made a friendly wager of epic proportions. The stakes: If the Patriots won, Bloomberg agreed to ship up to Boston with a truckload of the Big Apple's signature foods: pastrami and corned beef sandwiches from Carnegie Deli, 42 Big Blue Cheese Eli Mann-Eater burgers from Gallagher’s Steak House, one case of beef cocktail patties, one case of chicken cocktail patties, 5 pizzas, 42 pounds of rugelach, 42 pounds of layer cakes and cookies from Junior’s, 5 gallons of ice cream, 100 servings of Manhattan clam chowder, one bushel of Blue Point Oysters, 20 pounds of porterhouse steak from Peter Luger’s, and 6 bottles of Luger’s steak sauce.

But Tyree snagged that famous catch on his helmet, and Bloomberg's truckload stayed in New York.

Instead, Menino had to send New York: 100 Cups of New England clam chowder, 42 pounds of Dunkin’ Donuts coffee, 12 dozen Boston cream pies, 12 dozen Parker House rolls, 100 Old Tyme hot dogs, 100 Alfresco chicken sausages, 20 pizzas, 5 gallons of ice cream, 5 cases of yogurt bars, and 100 servings of Stonyfield Farm organic yogurt.

But Bloomberg and the NYC government made the right call: They donated the food to City Harvest, an organization devoted to combating New York’s fight against hunger.

5 Best Plays in Super Bowl History >>>

One of the first bets between governors was also one of the weirdest. Before the '83 game, Virginia Governor Charles Robb and Florida Governor Bob Graham made a friendly wager. In a nod to the “Hogs,” as Washington was affectionately nicknamed,  Robb offered to bet a live pig named Josephine. On the other side, Graham bet 3,000 bees, a reference to the Dolphins’ “Killer B’s” defense.

The Redskins won the game 27-17. We can only assume that no animals were hurt during the transfer process.

5 Kettlebell Exercises For Beginners >>>

After his Texas-sized hauls in 1996 and 1998, Giuliani was at it again in '99. This time, though, Giuliani strayed from his proven strategy and bet on the Mets, who promptly lost to the Braves in the NLCS. Giuliani was finally on the hook.

The solution? Since the 1999 World Series featured the Yankees and the Braves, Giuliani went double or nothing with Atlanta Mayor Bill Campbell. The Yankees swept the Braves and Giuliani took home two slabs of ribs, two cases of Georgia peanuts, two cases of locally brewed ale and a Hank Aaron autograph.

Super Bowl XXXIX featured the Patriots and the Eagles, two team nicknames that embodied America.

Naturally, when Pennsylvania Governor Ed Rendell and Massachusetts Governor Mitt Romney made their wager, they took the cities’ rich histories into account. The bet: loser’s governor had to sing the National Anthem at a basketball game in the winner's town.

After the Patriots defeated the Eagles 24-21, Rendell shipped up to Boston to sing the National Anthem before a 76ers–Celtics game. Rendell not only sang the Star Spangled Banner, he did so alongside his wife...who just so happened to be an opera singer. Their rendition was so good that it inspired (or not) Allen Iverson to score 38 points and lead the 76ers to victory.

Allen Iverson is Still Out Here Talkin' About Practice >>>

Leave it to Peyton Manning to bring home a pizza. (And that was before he became the Papa John’s spokesman.)

In 2007, Indiana Governor Mitch Daniels made a cordial bet with Illinois Governor Rod Blagojevich. The Indianapolis Colts blew out the Chicago Bears, making Daniels a double winner. Daniels received cheesecake, chocolate beer, taffy apples, toffee, and famous Chicago-style deep-dish pizza from Lou Malnati's.

Peyton Manning Loses a Game of Egg Roulette >>>

In 2009, the Yankees won the World Series battle between Broad St. and Broadway, defeating the Phillies four games to two. Not only did the Bronx Bombers get to take home their 27th World Series trophy, but they also got some free labor. In a bet that was the first of its kind, a month after the world series, Philadelphia Mayor Michael A. Nutter traveled to New York to paint a Bronx school while wearing the jersey of Hideki Matsui, the Yankees' World Series MVP. New York City Mayor Michael Bloomberg would have painted a school in Philly had the Phillies won.

Remember When Randy Johnson Blew Up a Bird? >>>

The Penguins dominated the 2016 Stanley Cup Finals. Even though San Jose took two games, the Penguins out-shot the Sharks 206-137 and left little doubt which team was better. Before the final started, Pittsburgh’s Carnegie Museum of Art reached out to the San Jose Museum of Art, asking to bet on the finals, and San Jose answered the call.

The stakes: The loser’s city would have to loan the winner’s city a piece of art. The Carnegie ended up wagering “Measurement Plant (Palm)” (1969), a work created by Pittsburgh native Mel Bochner, while the SJMOA bet “Mom Posing by Green Wall and Dad Watching T.V.” (1984), a photo by the California based artist Larry Sultan.

Hopefully the people of San Jose weren't too attached to the Sultan piece too much, because it’s headed for a long vacation in the Steel City.

The 10 Best Stanley Cup Playoffs Goals of All-Time >>>


Want more Men's Fitness?

Sign Up for our newsletters now.