Canadian Politicians vs. American Politicians: Who’s better at betting on sports?

The Toronto Blue Jays, alas, are on the sidelines now as the Cleveland Indians — triumphant over “Canada’s team” in the American League Championship Series — continue their battle with the Chicago Cubs for World Series supremacy.

But one notable Jays’ fan, Toronto Mayor John Tory, can still overcome the bitter taste of defeat to Cleveland by savouring the club’s earlier Divisional Series victory over the Texas Rangers — and the tasty barbecued brisket he won in a bet with his mayoral counterpart from Dallas.

Before the ALDS began between the Jays and s Rangers, Tory was challenged to a friendly wager — via Twitter — by Dallas Mayor Mike Rawlings. Rawlings said he was willing to bet some Texas brisket in favour of the Rangers if Tory was willing to put some Canadian beer on the table for the Blue Jays.

Tory quickly accepted and the bet was on between the two mayors.

The Blue Jays would go on to sweep the Rangers 3-0 in the series, advancing to the ALCS and earning a memorable divisional win for Canada — plus the beefy prize for Tory.

Frequently in recent years, whenever a Canadian sports team faces off against an American club in a playoff series or international competition, the cross-border rivalry draws in politicians keen to grab some limelight by challenging their U.S. or Canadian counterpart to a bet on the outcome.

So while Tory awaits his shipment of brisket from Texas, let’s look back at some other bets between Canadian and U.S. politicians to see which country has produced the better gamblers.

Larry O’Brien Doubles Down in 2007

In 2007, then-Ottawa mayor made a bet with Buffalo mayor Byron Brown on the outcome of the Senators-Sabres battle for the NHL Eastern Conference title. Since O’Brien and Brown were the 58th mayors of their respective cities, 58 was the magic number for the bet.

O’Brien wagered 58 bottles of maple syrup, 58 baseball hats from the city’s police, fire and paramedic servicees, and 58 saplings. In return, Brown bet 58 trees, 58 ball caps and 58 beef sandwiches — a Buffalo specialty. Each mayor also threw in a case of local beer to top things off.
O’Brien hauled in his winnings after the Sens won the series 4-1.

With the Sens facing the Anaheim Ducks in that year’s NHL finals, O’Brien and Anaheim mayor Curt Pringle upped the ante.

If the Senators took home the Stanley Cup, Mayor Pringle and his council would have to wear Sens jerseys and RCMP Stetsons, along with flying the Senators and Canadian flags at city hall. If the Ducks won the Cup, O’Brien and his fellow Ottawa council members would wear Ducks jerseys and Mickey Mouse Ears, and fly the Ducks and U.S. flags above Ottawa’s city hall.

The Ducks took the Cup in five games, and Ottawa’s mouse-eared mayor was soon working under the Stars and Stripes.

Harper gets the hat trick against Obama

Say what you will about Stephen Harper’s tenure as prime minister. But when it came to betting against U.S. President Barack Obama, Harper knew when to make his move.

The first bet between the two leaders came during the 2010 Vancouver Winter Olympics when Canada met the U.S. in the gold medal hockey game. The bet was straightforward: Harper would get a case of Molson Canadian if Canada won; Obama would receive a case of Pennsylvania-brewed Yuengling if the Americans won gold.

Canada, memorably, won thanks to Sidney Crosby’s “golden goal” and Harper collected his amber prize. U.S. Ambassador David Jacobsen personally delivered Harper the case of Canadian — plus an extra case of Yuengling courtesy of Obama.

Then, during the 2014 Sochi Winter Olympics, the two leaders made the same bet — twice —as Canada played the U.S. in both the men’s hockey semi-final and the women’s gold medal game. Canada was victorious in both matches and Obama shipped Harper two more cases of beer.

Vancouver mayor, B.C. premier bet on Canucks for 2011 Stanley Cup

Stanley Cup fever hit Vancouver fans hard when the Canucks faced the Boston Bruins in the 2011 NHL finals. And the series brought out the gambling spirit of B.C. politicians.

Vancouver Mayor Gregor Robertson and then-Boston mayor Thomas Menino made a multi-layered bet in favour of their beloved teams. If Vancouver won, Menino would have to pony up some fresh Boston lobsters, local Boston beers and a personal donation to Robertson’s charity of choice — then raise a Canucks flag at city hall for a day.

If Boston won, Robertson would send wild B.C. smoked salmon, some Vancouver craft beers and a charity donation to Boston — and raise the Bruins flag above Vancouver city hall.

A confident Robertson insisted on increasing the stakes by having the losing mayor wear a full-body spandex suit in honour of Vancouver’s famous Green Men. But Menino refused to accept that part of the bet.

B.C. Premier Christy Clark also got in on the action as she made a similar wager with then-Massachusetts governor Deval Patrick. If the Canucks won, Clark would receive Massachusetts clam chowder, and if the Bruins won Patrick would receive Nanaimo bars and smoked salmon. The loser would also have to wear the winning team’s jersey.

The most obscure bet from the 2010 series came between Stanley Park in Vancouver and Stanley Park in Boston. The winning park would receive a new bench dedicated by the losing park.

The series went the distance. The Bruins won Game 7 and left Vancouver with the Stanley Cup,a bounty of goods for the governor and Boston mayor, and a nice park bench.

Toronto and Brooklyn get musical in 2014

There was a lot of hype surrounding the Toronto Raptors and Brooklyn Nets as the faced off in the first round of the 2014 NBA playoffs — especially after Raptors general manager Masai Ujiri infamously yelled “F— Brooklyn” before Game 1 in Toronto.

In the wake of Ujiri’s crude utterance, Brooklyn Borough president Eric Adams wrote a letter to then-Toronto mayor Rob Ford making a friendly wager as a way to promote good relations between the two cities. The two sides agreed to a simple bet that would see the winner receiving a CD of their favourite local artist, courtesy of the losing mayor.

Brooklyn swept the Raptors 4-0 and it cost Ford a CD — “anything but Justin Bieber,” Adams insisted.

Montreal wins back-to-back over Boston

The Montreal Canadiens-Boston Bruins rivalry is one of the oldest in the NHL, and that history spurred Montreal Mayor Denis Coderre and Boston Mayor Marty Walsh to place their bets over the 2014 NHL Eastern Conference semi-finals.

If Montreal won, Walsh would have to wear a Canadiens jersey and fly a Habs flag over Boston City Hall for a week; Coderre and Montreal would do likewise if the Bruins won.

Montreal won the series 4-3 Walsh donned Montreal’s colours.

The next year, when the Canadiens and Bruins played in the 2016 NHL Winter Classic, the two mayors made another bet on that game.

This time, the losing mayor would have to put together a list of the 10 greatest things about the winning city. Montreal skated to a 5-1 and Walsh became the city’s temporary publicist.

Kansas City and Toronto get dramatic in 2015

Before the 2015 American League Championship Series between the Jays and the Kansas City Royals, Kansas City mayor Sly James challenged Tory in a YouTube video backed by a bunch of Royals fans. James said he was willing to offer ribs and sauces from three of his city’s top barbecue restaurants against “something good” from Tory’s Toronto.

Tory responded with a video of his own from in front of Toronto’s city hall, wagering a selection of Toronto-made beer. But Tory warned James that: “Number one, our beer is stronger, number two, our pitchers are stronger, and number three, our hitters are stronger.” Then he flipped a baseball bat like Blue Jays slugger Jose Bautista.

Despite his tough talk and haughty gesture, Tory would have to eat his words — not tasty ribs — as the Royals won the series 4-2.