Special Report

25 Hardest Teams to Root For

Source: Quinn Harris / Getty Images Sport via Getty Images

10. Chicago White Sox
> World Series: 3
> Playoff appearances: 9
> Last playoff appearance: 2008
> Win-loss pct.: 50.2%

The Chicago White Sox, a team that has been playing since 1901, has made it to the postseason just nine times. The team has not made it into the playoffs since 2008. The Sox had one of the longest championship droughts in American sports history, not winning a World Series between 1917 and 2005. Despite the postseason struggles, the White Sox have a winning percentage of greater than 50%.

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9. Minnesota Timberwolves
> Championships: 0
> Playoff appearances: 9
> Last playoff appearance: 2018
> Win-loss pct.: 39.6%

The Minnesota Timberwolves are the epitome of a boom or bust franchise. The team missed the playoffs in its first seven seasons. After drafting Kevin Garnett, the T-wolves made the playoffs eight straight years but were bounced in the first round seven times. Since then, Minnesota had a 13-year playoff drought before snapping it in the 2017-2018 season, led by All-Star center Karl-Anthony Towns. In the 2018-2019 season, the T-wolves reverted to form and failed to make the playoffs. This season, the team is one of the worst in the league, going 19-45 before the season was shut down.

8. Philadelphia Phillies
> World Series: 2
> Playoff appearances: 14
> Last playoff appearance: 2011
> Win-loss pct.: 47.2%

Throughout their history, the Philadelphia Phillies have lost over 11,000 games — more than any other franchise in American professional sports. Despite playing since the 1880s, the Phillies have won the World Series just twice, in 1980 and 2006. Philadelphia is one of just seven MLB teams that have won less than 47.5% of their games, and they have only made it to the postseason about once a decade. The team has not made the postseason since losing the NLDS to St. Louis in 2011.

Source: Joe Robbins / Getty Images

7. Tampa Bay Buccaneers
> Super Bowls: 1
> Playoff appearances: 10
> Last playoff appearance: 2008
> Win-loss pct.: 38.7%

Tampa Bay Buccaneers won their only Super Bowl in 2003, and they have not made the playoffs since 2007, when they lost the wild card game. The Bucs were hoping that quarterback Jameis Winston, drafted out of Florida State University, would return Tampa Bay to the Super Bowl. That did not work out as Winston has only led the Bucs to one winning season before signing with New Orleans. Now, with Super Bowl champions Tom Brady and Rob Gronkowski on the team, Bucs fans have a reason to be excited.

Source: Mike Ehrmann / Getty Images

6. Florida Panthers
> Stanley Cups: 0
> Playoff appearances: 5
> Last playoff appearance: 2016
> Point pct.: 49.9%

The Florida Panthers have made the playoffs just five times in the 24 years of the franchise’s existence. In the Panthers’ third season in 1995-96, the team made the Stanley Cup Finals but lost. Since then, they’ve never made it past the first round. They made it into the league’s unusual 24-team playoff format as a result of a COVID-19-shortened season in 2020, but they were eliminated in the play-in round by the Islanders in four games.

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