Four Teams or more
Boston-Boston Red Sox (2007)
Los Angeles/Anaheim-Anaheim Ducks (2007)
Miami-Miami Heat (2006)
St. Louis-St. Louis Cardinals (2006)
Chicago-Chicago White Sox (2005)
Detroit-Detroit Pistons (2004)
New York City and East Rutherford-New Jersey Devils (2003)
Phoenix-Arizona Diamondbacks (2001)
Denver-Colorado Avalanche (2001)
Dallas-Dallas Stars (1999)
Atlanta-Atlanta Braves (1995)
Washington DC-Washington Redskins (1991)
Minneapolis-Minnesota Twins (1991)
Philadelphia-Philadelphia 76ers (1983)
Cleveland/Columbus-Cleveland Browns (1964)
Pittsburgh-Pittsburgh Steelers (2006)
Charlotte-Carolina Hurricanes (2006)
Tampa-Tampa Bay Lightning (2004)
Green Bay/Milwaukee-Green Bay Packers (1996)
Houston-Houston Rockets (1995)
Toronto-Toronto Blue Jays (1993)
Oakland-Oakland Raiders (1980) Note: The Raiders won a championship in Los Angeles in 1983
Seattle-Seattle Supersonics (1979)
Indianapolis-Indianapolis Colts (2007)
Baltimore-Baltimore Ravens (2000)
San Francisco-San Francisco 49ers (1994)
Cincinnati-Cincinnati Reds (1990)
Kansas City-Kansas City Royals (1985)
San Diego-Never Note: The Chargers won an AFL Championship in 1963
Buffalo-Never Note: The Bills won an AFL championship in 1965, but never an NFL Championship.
San Antonio-San Antonio Spurs (2007)
Montreal-Montreal Canadians (1993)
Edmonton-Edmonton Oilers (1990)
Calgary-Calgary Flames (1989)
Portland-Portland Trail Blazers (1977)
Ottawa-Ottawa Senators (1927)
As you can see, Cleveland sports fans haven't been able to celebrate a championship since the 60s, even though they have four teams. The Blue Jackets are pretty new to town, so it's understandable that they haven't won, but the Cavs, Browns, and Indians have been around forever. It's been a while. It would not be a stretch to say that New Orleans fans have suffered the most. The Saints have been awful forever now, they lost the Jazz in the 70s, and they just recently got another bad team, the Hornets. It's hard to say that cities like San Jose, Orlando, Jacksonville, Sacramento, and Ottawa have suffered. Their franchise is fairly new to town. Vancouver has had the Canucks for a while now. Buffalo is surprising. They have had two teams for a long time now. The Bills lost in four straight Super Bowls.In my mind, here are the five worst towns to be a sports fan in. These are in order.
1. Cleveland-The Blue Jackets are nothing special. The Cavs made their first Finals last year. The Browns have been awful almost every year since the 60s. The Indians haven't won since Bob Feller was their ace.
2. Philadelphia-The 76ers may be the worst team in the league this year, and they traded away Iverson for a group of scrubs. The Eagles lost a close one in the Super Bowl a few years ago. The Flyers aren't terrible, but they haven't won anything for a while. The Phillies are wishing Mike Schmidt never aged.
3. Seattle-The Mariners were amazing with Griffey, Rodriguez, and Johnson, but they never won it all. The Seahawks were close, but they couldn't beat the Steelers. The Supersonics haven't been good since Shawn Kemp and Gary Payton were their 1-2 punch.
4. New Orleans-The Saints just made it to their first NFC Championship Game last year after 35 years of futility. They couldn't retain the Jazz, and now they might lose the Hornets.
5. Buffalo-Four straight losses in the Super Bowl? That has to be the most painful stretch for any city.