Go back

History’s Greatest Friendly Political Wagers

The “Friendly Political Wager” is one of the great traditions of both sports and politics. Symbolic bets between two rival city’s political leaders is one of the most fun and creative practices in existence and they often eclipse the main event itself. You probably don’t remember who won Game 7 of the Canucks-Bruins series in 2011 but I know you definitely didn’t forget when mayor Gregor Robinson had to go in public wearing a yellow and black jersey! What a fun-loving, down-to-earth and cool guy! Who wouldn’t want to get a beer with him and then vote for him in the next election?

Anyway, here’s a list of some of the wackiest, most outrageous and, of course, greatest friendly political wagers of ALL TIME!

Julius-Caesar-Eleanor-Qu

Event: Ultimate Gladiator Championship 147

Participants: Julius Caesar and Arisnoe IV of Egypt

The Bet: If Caesar’s championed Roman gladiator, Maximus, were to win the big fight Arisnoe agreed to deliver him a jar of Alexandria’s Egyptian Pale Ale, her favourite beer, while wearing a Caesar-style leaf crown. If Arisnoe’s pick, a nameless Egyptian slave and man-eating tiger tag-team, were to win, Caesar promised to erect a Sphinx statue in the middle of Rome and leave it there until the start of the next gladiating season.

Outcome: I think it goes without saying, but Maximus was victorious at UGC 147 and Arisnoe had to deliver Caesar the jar of beer, although Caesar lessened her embarrassment by gracefully choosing not to use this opportunity to have her publicly executed.

british-mayor-Eleanor Qu

Event: 1888 FA Cup Final

Participants: West Bromwich Mayor, Tom Gilroy and Preston Mayor, Earl Tinney

The Bet: If Gilroy’s home club West Bromwich Albion F.C. were to take home the coveted FA Cup, Tinney agreed to wear a throstle’s nest on his head for the remainder of his mayoral term. If Preston North End F.C. won however, Gilroy would have to appoint a sheep as his vice-mayor.

Outcome: West Bromwich triumphed over North End in a 2-1 victory and since that day every mayor of Preston, Lancashire has spent the entirety of their mayoral career wearing a bird’s nest on their head, one of the town’s proudest traditions.

Charles-De-Gaulle-Eleanor Qu

Event: The Battle of France (September 1939)

Participants: Charles De Gaulle and Adolph Hitler

The Bet: If the Allies could prevent the German Army from capturing France, Hitler agreed to wear a french beret for the remainder of WW2. If the Nazis won, De Gaulle promised to wear and be photographed in the opposing side’s uniform.

Outcome: Despite outnumbering their opponents, the Allies just couldn’t handle the German Army’s strategy and were quickly defeated. France was divided into German occupation zones and an embarrassed De Gaulle was forced to wear one of Hitler’s old uniforms for which he received a lot of ribbing from his fellow political leaders.

JFK-Eleanor-Qu

Event: USA/Cuba Exhibition Baseball Game (1961)

Participants: John F. Kennedy and Fidel Castro

The Bet: If the US were to win the game against Cuba, Castro agreed to send JFK a box of authentic Cuban cigars. If Cuba were to win though, Kennedy promised to wear a T-shirt that featured the Cuban Revolution hero of Castro’s choice.

Outcome: Cuba won the game by a score of 7 to 4 and JFK agreed to wear a shirt depicting Ernesto “Che” Guevara. Despite the ironic intentions, the look was so popular that the shirt was mass produced and remains a staple of American mall T-shirt shops to this very day.

 

Event: 1972 United States Presidential Election

Participants: Spiro Agnew and Sargent Shriver

The Bet: In order to entertain themselves as they waited to see if their bosses would be elected, Richard Nixon and George McGovern’s running mates held a side bet on the results of the election. If Nixon won, Shriver would have to wear a Nixon-mask to the next Kennedy family function while in the case of a McGovern victory, Agnew would have to wear a Republican party baseball cap while serving a month’s service in the Vietnam War.

The Outcome: Nixon won the election and Shriver, who was a member of the Kennedy family wore the mask to their next event which happened to be a soiree dedicated to the 4th anniversary of the passing of Bobby Kennedy. It was the last party Shriver was ever invited to.

 

Event: 2007 Nathan’s Hot Dog Eating Competition

Participants: George W. Bush and Yasua Fukuda

The Bet: Japanese prime minister, Yasua Fukudu agreed that if world-champion Japanese competitive-eater Takeru Kobayashi lost to any of his American competitors, he would shave the US flag into the back of his head. For his part, Bush promised that if Kobayashi did win, he would have a map of Japan tattooed on his chest.

The Outcome: After six straight victories at Nathan’s, Kobayashi was finally defeated by American, Joey Chestnut. Fukudu would honour his commitment, although some have called foul on the cut which only had 30 stars instead of the traditional 50.

obama-Eleanor Qu

Event: Canada-US Olympic Hockey Semi-final Match (Sochi 2014)

Participants: Stephen Harper and Barack Obama

The Bet: While publically the bet was a simple exchange of beers from each other’s nation, behind closed doors the bet was a little more involved. If Canada won, it was agreed Obama would have to shotgun the 6-pack of beer Harper got him right before speaking to Russian president Vladimir Putin about the Crimea situation. If the US won, Harper was to officially change the Canadian national anthem to Loverboy’s “Working for the Weekend”.

Outcome: Canada came through with a huge win against the US and Obama had to kill six Molsons before getting on the phone with Putin. While he did have a good plan for resolving the situation, he decided instead to let Putin know how he really felt about him for three hours before crying and hanging up.

Was this article helpful?
0
0

Leave a Reply

Block title

SFU professor highlights the danger BC faces from natural disasters

By: Niveja Assalaarachchi, News Writer 2025 was one of the most destructive years on record for natural disasters. Though much of the damage to infrastructure and human lives was seen in the Global South, much of the economic cost was seen in Global North countries like Canada. The Peak interviewed Tim Takaro, a professor emeritus at SFU’s faculty of health sciences, to learn more about how the growing destruction of natural disasters specifically applies locally.  In 2025, BC faced disasters like the flooding of the Fraser Valley and forest fires. Takaro explained that these disasters as a whole had afflicted large segments of the population, especially marginalized communities. For one, he pointed to those with chronic illnesses, as chronic conditions can increase the chances of sickness...

Read Next

Block title

SFU professor highlights the danger BC faces from natural disasters

By: Niveja Assalaarachchi, News Writer 2025 was one of the most destructive years on record for natural disasters. Though much of the damage to infrastructure and human lives was seen in the Global South, much of the economic cost was seen in Global North countries like Canada. The Peak interviewed Tim Takaro, a professor emeritus at SFU’s faculty of health sciences, to learn more about how the growing destruction of natural disasters specifically applies locally.  In 2025, BC faced disasters like the flooding of the Fraser Valley and forest fires. Takaro explained that these disasters as a whole had afflicted large segments of the population, especially marginalized communities. For one, he pointed to those with chronic illnesses, as chronic conditions can increase the chances of sickness...

Block title

SFU professor highlights the danger BC faces from natural disasters

By: Niveja Assalaarachchi, News Writer 2025 was one of the most destructive years on record for natural disasters. Though much of the damage to infrastructure and human lives was seen in the Global South, much of the economic cost was seen in Global North countries like Canada. The Peak interviewed Tim Takaro, a professor emeritus at SFU’s faculty of health sciences, to learn more about how the growing destruction of natural disasters specifically applies locally.  In 2025, BC faced disasters like the flooding of the Fraser Valley and forest fires. Takaro explained that these disasters as a whole had afflicted large segments of the population, especially marginalized communities. For one, he pointed to those with chronic illnesses, as chronic conditions can increase the chances of sickness...