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City of Losers: Cleveland, Toronto carry long history of heartbreak

Rich Arden/ESPN/Handout / Reuters

There aren't two cities in North America with more tortured sporting histories than Toronto and Cleveland, who are squaring off for a spot in the NBA Finals.

Toronto hasn't hosted a championship parade since 1993, while Cleveland's infamous drought dates back to 1964. Futility, disappointment, anguish, and anger - both cities have seen more than their fair share.

Toronto Maple Leafs

For a city enamored with hockey, love has been a one-way street. Torturous doesn't come close to detailing the futility of the Maple Leafs.

Full generations have passed since puck-crazed fans last saw the Leafs hoist the Stanley Cup in 1967. Since then, the Leafs have made four conference finals, but no farther.

The past decade has been especially lean. They've made one playoff appearance in the last 11 years - and that featured the Leafs blowing a three-goal, third-period Game 7 lead to the Boston Bruins.

Fortune might finally swing for the Leafs as they hold the No. 1 pick in the upcoming draft, but that only came about after the once-proud franchise finished with the NHL's worst record.

Cleveland Browns

It's been nothing but misery since Jim Brown carried Cleveland to the championship in 1964.

Since then, the Browns have been a model of instability. They've had five straight last-place finishes in their division. They've had one winning season since 2001. Before that, they made 14 playoff runs without sniffing the Super Bowl. They've battled middling owners, and zero continuity. They've sold fans on a slew of draft busts, including Trent Richardson, Brandon Weeden, and Johnny Manziel.

Cleveland even lost the Browns for a season before the franchise was re-established.

Cleveland Indians

The grounds crew in "Major League" said it best: "They're still shitty."

The Indians' last championship came in 1948. Since then, they've made three World Series appearances, only to lose each time - most recently in 1997 when a heavily favored Indians team lost in seven games when Game 7 was decided in extra innings on a softly hit single up the middle that bounced off a glove.

And, of course, the team's name is a matter of controversy.

Toronto Blue Jays

Like most expansion franchises, the Toronto Blue Jays toiled through some tough times in their first decade of existence. But the fanbase never wavered, and they were rewarded with a five-year stretch between 1989-1993 that featured four playoff appearances and culminated in back-to-back World Series titles.

Nothing was the same after Joe Carter touched them all.

The Jays then fell into one of the longest playoff droughts in North American sporting history with 21 years of unending futility. The bluebirds managed to be competitive, fielding nine teams that finished above .500, but they were the picture of mediocrity until one bat flip changed the narrative.

Cleveland Cavaliers

The two harrowed phrases that can never be uttered around Cavaliers fans: The Shot and The Decision. That's enough baggage for any franchise to carry.

But more than anything else, it's the disappointment that's weighed on Cavaliers fans. They've had nine years of LeBron James and no championships to show for it. Before the King rolled through, the Cavaliers suffered 10 first-round exits between two battles with Michael Jordan.

Having the audacity to hope was, and continues to be, the bravest act of any Cavaliers fan.

Toronto Raptors

The Toronto Raptors were doomed ever since Isiah Thomas' toothy grin burst through a cartoon dinosaur. Basketball has always been - and remains - the second fiddle (at best) in a hockey-crazed town, and quite frankly, the Raptors never gave the city much reason to be excited.

The halcyon days saw Vince Carter wowing crowds with breathtaking athleticism, but his teams only made three playoff runs and never moved past the second round. It looks great in highlight packs, but in truth the Raptors were a 47-win team at Carter's peak.

Carter's era ended on a sour note and his exit gave way to the harrowing trend of stars fleeing the north. Damon Stoudamire, Tracy McGrady, Chris Bosh - every player worth a damn jumped back to the U.S. where "the good cable" flowed freely.

Up until this season, the Raptors hadn't even won a seven-game series, hadn't moved past the second round, and never reached the 50-win plateau. This year's run has been a long time coming.

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