Lovable Losers: Part One

[Washington, DC-based Ezra Troy offers the first of two articles on a topic that will be (devastatingly) dear to the hearts of anyone that resides in one of the cities on this list.  He alliteratively calls it, Lovable Losers.  The key thing, of course, is loving your team whether they are good or bad.  No one respects bandwagon fans.]    

With the Cavaliers winning the NBA championship, they broke the second longest active championship drought for a city with at least two pro sports teams. Now that Cleveland’s 51-year drought is over, what are the longest active championship droughts for cities with at least two cities?

Big League Cities with the Longest Droughts 

San Diego – 53 years

The California city has two teams, the Chargers and the Padres. The Chargers have been to the playoffs 18 times in the Super Bowl era, but have only made one Super Bowl! Meanwhile, the Padres have lost the two World Series they made, winning only one game in the process. To find the last time San Diego won a championship, one has to go back to one year before the Browns won Cleveland’s last championship before this year – 1963.


Buffalo – 51 years

Since their founding in 1970, the Buffalo Sabres have made three Stanley Cups but lost them all. The other Buffalo team, the Bills, made four Super Bowls in a row… and lost them all! The last championship won by Buffalo was the Bill’s AFL titles in 1964 and 1965.

Milwaukee – 45 years

The last Milwaukee championship was the NBA championship in 1971, when the Bucks had Kareem Abdul – Jabar (then Lew Alcindor) and Oscar Robertson. Then the Bucks traded Kareem, and Milwaukee hasn’t won a major championship since. (The other Milwaukee team, the Brewers, have never won a World Series.)

Teams with the Longest Droughts

Even though these teams had other teams in their cities win championships, they have long title droughts themselves. (teams that have never won a championship are not included)

Chicago Cubs – 108 years

The quintessential example of a championship drought in sports is that of the Chicago Cubs. The last time the Cubs won the World Series, Google was 90 years away from being born, Theodore Roosevelt was finishing up as the 26th president of the US and the first Model T was being produced. In addition to not winning for 108 years, the Cubs haven’t even made the World Series since 1945. According to legend, they were cursed by a man wanting to bring his Billy Goat into a game of the 1945 World Series. They haven’t a world series  since. Things that have prevented them, most notably 2003 and the Steve Bartman game, have all been attributed to the Billy Goat curse.


Arizona Cardinals – 69 years

The Cardinals are the league’s oldest franchise, founded in 1898. They only have won one title (and another disputed one) since their founding. The title came in 1947; they are still waiting for another. In the 69 years of waiting, they have won 8 playoff games, two last year and another three when they went to the Super Bowl in 2010.

Cleveland Indians – 68 years

Part of the long city championship drought just broken by the Cavaliers, the Indians are now the biggest loser in a city of losers. After beating the Braves in 1948, the Indians have only made the Fall Classic once since they brought home that first title. (But they lost to the Atlanta Braves in six games in 1995).

It is a tough list.  Unfortunately, there are multiple ways to look at poor performance and underperformance against expectations when it comes to professional sports.  I will touch a couple of more variants in my next installment of this series on Lovable Losers.

Ezra Troy

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2 comments on “Lovable Losers: Part One
  1. WGT says:


    I liked your article. The Royals had not won the World Series since 1985. Then, in 2015, they did it in 30 years. #curry30 Miracle do happen. These teams could win it. #indianscubshaveachance

  2. G-Turbo says:

    The Indians are doing really well this year. The Cubs especially are doing well. One of them could win the World Series. Who will it be? It will probably be the Royals. #youcan’tstealourcrown #royalsrule #wizardofhos #miracleshappen #insaneforcain

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