Special Report

Once Great Sports Franchises That Have Fallen on Hard Times

Source: Patrick Smith / Getty Images

11. Baltimore Orioles
> League: MLB
> Most recent playoff appearance: 2016
> Total championships (most recent): 3 (1983)
> Recent playoff performance: one postseason series win since 1997

The Baltimore Orioles had an extended run of success from 1966-1983, making the World Series six times and winning three titles. But the O’s have faced stiff competition from AL East foes like the Yankees and Red Sox and have struggled to make it to the postseason. After their 1983 title, Baltimore did not make the playoffs again for over a decade, and when they did, they lost in the ALCS in 1996 and 1997. The Orioles’ most recent postseason bids ended in the 2012 ALDS, the 2014 ALCS, and the 2016 wild card game. Baltimore finished last in their division each of the last three seasons. Attendance has plummeted as the Orioles lost over 100 games in 2018 and 2019.

Source: Maddie Meyer / Getty Images

10. Toronto Maple Leafs
> League: NHL
> Most recent playoff appearance: 2019
> Total championships (most recent): 13 (1967)
> Recent playoff performance: one postseason series win since 2002

The Toronto Maple Leafs won 13 Stanley Cups in their first 50 seasons — and none in the next 51. The last Toronto title came in 1967, and the Leafs have not earned a spot in the Finals since. Toronto made the playoffs six straight seasons from 1999-2004, making it as far as the conference finals in 2002. After a labor dispute canceled the 2004-2005 season, the Maple Leafs missed seven straight postseasons. Since then, the team lost in the 2013 first round, missed three more postseasons, and then suffered three straight first-round exits from 2017-2019.

Source: Leon Halip / Getty Images

9. Detroit Pistons
> League: NBA
> Most recent playoff appearance: 2019
> Total championships (most recent): 3 (2004)
> Recent playoff performance: no postseason series wins since 2008

Detroit’s “Bad Boy” Pistons made nine straight playoff appearances from 1984-1992, earning three Finals appearances and two championships. Detroit enjoyed another long playoff streak from 2002-2009, winning the 2004 title. Since then, the Pistons have made the playoffs just twice — exiting in the first round in 2016 and 2019. In February 2020, the Pistons traded their top player Andre Drummond, signaling the franchise was rebuilding.

Source: Patrick Smith / Getty Images

8. Washington Redskins
> League: NFL
> Most recent playoff appearance: 2015
> Total championships (most recent): 5 (1991)
> Recent playoff performance: one postseason win since 2000

The Washington Redskins are one of just nine teams that has won at least three Super Bowls. Coach Joe Gibbs led Washington to titles in 1982, 1987, and 1991. The Redskins have sputtered in the years since, and their most recent playoff win, in 2005, came in Gibbs’ second stint at the helm. Since then, Washington made the playoffs in 2007, 2012, and 2015, losing by double digits in the wild card round each time.

Source: Mike Powell / Getty Images

7. Edmonton Oilers
> League: NHL
> Most recent playoff appearance: 2017
> Total championships (most recent): 5 (1990)
> Recent playoff performance: one postseason series win since 2006

After joining the NHL with a teenage Wayne Gretzky in 1979, the Edmonton Oilers won four Stanley Cups in the 1980s and a fifth in 1990, the last one largely thanks to players they netted from trading the Great One to the Los Angeles Kings. After that, the Oilers sputtered. The team has only made it past the second round of playoffs once since 1992, when they lost the 2006 Stanley Cup Final. The Oilers have only made the postseason once since, a second round exit in 2017. Edmonton’s new crop of young talented players seemed likely to propel the team to the 2020 postseason, but the NHL season was put on hold due to the COVID-19 pandemic.

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