The Weirdest Things Ever Wagered on Sporting Events

Laura Depta@lauradeptaFeatured ColumnistJune 11, 2014

The Weirdest Things Ever Wagered on Sporting Events

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    Betting and sports go together like Bill Belichick and hoodies—but sometimes, instead of just making things interesting, the wagering parties like to makes things very interesting.

    To really spice up a bet, either the terms need to be out of the ordinary, or the event itself does. Just how weird can it get? We’re going to find out.

    Recently, the mayors of New York City and Los Angeles made a Stanley Cup bet with nationally televised public humiliation at stake. An Olympian once agreed to wear an extremely tight, extremely neon male bathing suit to the opening ceremony.

    If bets and sports go together like Bill Belichick and hoodies, then weird bets and sports go together like Rob Gronkowski and bro-isms.

    Here are 15 strange wagers for your reading enjoyment.

    The honorable mention goes to Brandon Spikes and Roddy White’s Twitter antics.

NFL Parlay

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    In 2013, one NFL fan supposedly risked his life savings on a two-game parlay.

    Some guy who calls himself YouveJustBeenTanked on Reddit claimed to throw down over $65,000 on both the 49ers and Bengals covering in their Week 10 games. 

    It seems a little off to bet your life savings on a couple of football games (regular season games at that), and since he lost, the bet turned out to be a less than intelligent move. Then again, there are some who question the validity of this Reddit post to begin with (noooo).

Boston Roller Derby

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    In June 2012, two editors were apparently so bored with the state of sports (mid-June does kick off a bit of a slow period in sports) that they publicly decided to wager on women’s roller derby.

    Carly Carioli of the Boston arm of The Phoenix and Jeff Inglis of the Portland arm agreed to terms over a matchup between the Boston Massacre and the Maine Port Authorities.

    If the Massacre won, Inglis would eat a Poe Burger—a staple of Boston cuisine that has lobster, foie gras and black truffle stuffed into the meat. If the Port Authorities were victorious, Carioli would have to eat a wasabi lobster roll.

    Neither of those really seems like punishment, if you ask me, but the roller derby part is a bit odd.

    For those who are interested, roller derby results aren’t exactly as easy to find as, say, MLB scores, but it looks like Boston won.

Aaron Rodgers and Boyz II Men

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    Making bets with 90s boy bands? Yea, that’s sort of weird. According to TMZ Sports, in 2012, Aaron Rodgers made a bet with Boyz II Men and agreed to wear an Alex Smith jersey if his Packers lost to the 49ers.

    Shocker: the Packers lost to the 49ers. Rodgers later claimed the bet was “at best a joke between friends,” but it sure seemed like the band took it seriously.

Patriots and Giants Super Bowl

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    Here’s another gem from our friends at Reddit. Like many poor, innocent fools, imyourking12 bet on the 18-0 Patriots to win the Super Bowl in 2008.

    The problem here was that the terms of the bet included one item: a swift kick to the nuts. I’m no male, but I’ve heard that particular form of punishment is less than fun.

    Count it as just one more life ruined by David Tyree’s helmet.

Aaron Rodgers Defends Ryan Braun

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    What is with Aaron Rodgers making bets he doesn’t intend to follow through on? I’m starting to think that guy has no sense of humor to go with his lack of hand placement knowledge

    Even if you’re one of the highest paid players in the NFL, it’s still not smart to bet a year’s salary over Twitter—especially when your side of the bet is to contend that Ryan Braun did NOT do steroids.

    According to USA Today Sports, in 2013, Todd Sutton of Denver tweeted at Rodgers, calling him delusional for defending Braun against PED allegations. Rodgers responded with a tweet of his own, saying, “ya I'd put my salary next year on it.”

    We all know what happened next.

Christina Aguilera

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    Prop bets are a time-honored tradition associated with any major sporting event, and especially the Super Bowl.

    In 2011, one such bet included both how long Christina Aguilera would take to sing the national anthem and how long she would hold the last note, according to VH1.

    This seems like a weird thing to make a bet on, but the story is even funnier due to its results. Folks who took the over on the last syllable were happy campers, but those who took the over on the whole song, not so much. Xtina came in short…due to missing an entire verse. Lesson: don’t bet on pop stars.

    Other hilarious prop bets have included: how often a particular word or phrase will be mentioned in the broadcast, what color the Gatorade will be and headwear selections of musical performers.

Cross-Country Mayors

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    When the Los Angeles Kings crushed the repeat hopes of Chicago hockey fans on June 1, the Internet immediately exploded about L.A. and New York meeting in a major championship for the first time since the Yankees and Dodgers in 1981.

    The two teams have been light-heartedly jabbing each other on Twitter, and Will Ferrell even got involved. Naturally, the cities’ respective mayors decided to make a wager.

    The terms: No matter the outcome, someone is singing on Jimmy Kimmel Live!, according to

    If the Kings win, the tune of choice for New York City mayor Bill de Blasio is “I Love LA” by Randy Newman. If the Rangers come back to take the Cup, it’s “New York, New York” by Frank Sinatra for L.A. mayor Eric Garcetti.

Jason Terry’s Superstitions

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    Betting on a headband is not completely weird, but it is weird how seriously Jason Terry likely took it.

    According to, Terry and Jameer Nelson engaged in a CrossFit competition in 2012—the loser of which had to wear the winner’s shoes at the next meeting of their two teams (at the time, the Dallas Mavericks and Orlando Magic, respectively). In addition, if Terry lost, he would have to hang up his high socks and headband for the night.

    Terry lost and, therefore, had to give up one of his famous superstitions. He followed through, but did say, “I think I may get through the first quarter, but if I miss my first two shots, I'm gonna do a quick wardrobe change.”

Restaurants and Cheerleaders

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    Super Bowl XXXIII in 1999 was John Elway’s last career game (nothing like goin’ out on top). It was also the basis for a ridiculous bet between two Atlanta and Denver restaurant managers.

    According to, Willy Cellucci of the Atlanta Palm Restaurant lost big to Scott Fickling of the Denver Palm, and he paid the price.

    That price? Working as maître d’ for a night in Denver while donning a Broncos cheerleading outfit.

    “I’m gonna look great,” Celucci said. I wouldn’t bet on it.

Wedding Colors

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    So, I’m no wedding expert here, but leaving the colors up to chance seems like a pretty bad idea. An even worse idea? Leaving the colors up to chance when the only possible outcomes are either green and yellow or red and gold. That’s a loss any way you slice it.

    One betrothed couple (via claimed to let the outcome of the 49ers and Packers 2013 Week 1 matchup make this decision for them.

    I wonder how those bridesmaids looked walking down the aisle dressed like Colin Kaepernick.

Snow Removal

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    Super Bowl XLV. Green Bay vs. Pittsburgh. Mayor versus Mayor.

    When the Pack met the Steelers in the big game, Green Bay mayor Jim Schmitt and Pittsburgh mayor Luke Ravenstahl made a friendly wager, according to the Pittsburgh Post-Gazette.

    Said wager stipulated that the loser hang an opposing team banner in city hall, which is boring. But the terms also required the loser to shovel show from the residence of an opposing fan, which is pretty unusual, not to mention unintelligent given the February weather patterns in these two cities.


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    The forced donning of Borat’s mankini sure constitutes a weird punishment for losing a bet. But that’s exactly what happened to Olympic gold medalist Russell Mark. The Aussie shooter lost a wager made on an Australian Football League match, according to The Telegraph.

    His team’s loss forced Mark to accept the terms of his defeat—wearing the skimpy green suit to the opening ceremony of the 2012 Olympic Games in London.

    Mark agreed to take it like a man, but it’s challenging to find any evidence that he actually did.

Zoo Animals

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    The Toronto Blue Jays beat the Phillies of Philadelphia in the 1993 World Series. Prior to any game action, there was a bet between two…zoos?

    The Philadelphia Zoo promised rare white lions to match the Toronto Metro Zoo’s offer of Tasmanian devils (via Two white lions (one of which was the first ever born in the western hemisphere) were slated to visit Toronto the following year.

Shaq's Pink Undies

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    An athlete and a late-night host make a bet on a video game. Then someone ends up on national television wearing pink underwear.

    In 2012, Shaquille O’Neal and Jimmy Fallon played NBA Jam on Late Night with Jimmy Fallon. Jimmy won, and Shaq had to take a long two-block walk of shame (via Yardbarker).

    A real man owns up to his bets—a lesson Aaron Rodgers could certainly learn from Shaq Diesel.

Pigs and Honeybees

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    In 1983, the Washington Redskins beat the Miami Dolphins to win Super Bowl XVII. At the time, Virginia governor Charles Robb and Florida governor Bob Graham had quite the wager going, according to the Ottawa Citizen.

    If the Dolphins won, Robb would send Graham a pig—apparently a nod to Washington’s offensive line, nicknamed “The Hogs.”

    But instead the Redskins won, and Graham had to send Robb the promised 3,000 honeybees—in reference to Miami’s defense, nicknamed the “Killer Bees.”