Once Great Sports Franchises That Have Fallen on Hard Times

The Philadelphia Flyers have made the playoffs in 39 of their 52 seasons — a 75% rate. The Flyers advanced into the postseason each season from 1973 to 1989, winning the 1974 and 1975 Stanley Cups. Philly also missed the playoffs just once from 1995 to 2012, but the Flyers have been up and down since. They missed the 2013, 2015, 2017, and 2019 playoffs, and were bounced in the first round in 2014, 2016, and 2018.

The Oakland Raiders were one of football’s most dominant teams after the 1970 NFL-AFL merger. The team made 12 postseason appearances from 1970-1985, winning Super Bowls in the 1976, 1980, and 1983 seasons. Since then, however, the team won just two playoff games in the 1990s. And after losing the Super Bowl in 2002, Oakland’s only subsequent playoff appearance was a wild card loss to the Houston Texans in 2016.

Michael Jordan and the legendary 1990s Chicago Bulls won six championships, but the team has struggled since MJ left. Chicago missed the playoffs six seasons in a row following their sixth title. The 2010s Bulls, led by Derrick Rose, seemed to be title contenders before Rose tore his ACL in the 2012 playoffs. Chicago has never made it past the second round since. After firing coach Tom Thibodeau in 2015, the Bulls have earned a spot in the playoffs just once. The team seems to be shaking things up going into the 2020s, firing general manager Gar Forman in April.

The Philadelphia Phillies’ history stretches back to the 1880s, featuring seven World Series appearances and two titles. The Phillies’ most successful stretch was 2007-2011, when the team earned five straight postseason bids and won the 2008 World Series. Since then, Philadelphia has never finished a season above .500 or higher than third in its division.

The Chicago Bears have more Hall of Famers than any other team, with 26, and rank second in NFL championships, with nine. Still, titles have been hard to come by as of late, with the legendary 1985 Bears securing the most recent championship. Chicago had just three playoff wins since 1995, and the Bears’ lone postseason appearance since 2011 ended in a heartbreaking wild card round defeat. After an 8-8 2019 campaign, Chicago may be searching to replace former second overall pick Mitchell Trubisky at quarterback.

After moving around in the 1970s and 1980s, the Devils franchise found a home — and success — in New Jersey. The team missed the playoffs just once from 1990-2010, winning the Stanley Cup in 1995, 2000, and 2003. New Jersey struggled after that run, however. The Devils made the postseason just twice since 2010, losing in the 2012 Finals and the first round of the 2018 playoffs.

Head coach of the Miami Dolphins from 1970 to 1995, Don Shula took his team to the playoffs 16 times, appearing in five Super Bowls and winning two. His 1972 squad is still the only team to win a Super Bowl after an undefeated regular season. Miami has not won a playoff game since 2000, though. The team lost in the first round in 2001, 2008, and 2016.

The Pittsburgh Pirates are one of just eight MLB teams to win the World Series at least five times. Pittsburgh’s most recent title came in 1979, and the team has not won a postseason series since. The Pirates have earned six playoff berths after that 1979 title, losing in the first round in 1990, 1991, and 1992. Pittsburgh earned wild card spots in 2013, 2014, 2015, only advancing to the NLDS in 2013, where they lost in five games to their NL Central rival St. Louis Cardinals.

One of the Original Six NHL teams, the New York Rangers have won four Stanley Cups — in 1928, 1933, 1940, and 1994. The team has struggled in recent years, missing the postseason from 1998-2004. Even after making it back into the postseason consistently in the following years, the Rangers could not earn a title, making it as far as the Finals just once, in 2014. The Rangers finished last in their division in 2018 and next to last in 2019. Despite having a winning record, New York was on pace to miss the playoffs again in 2020.

The Detroit Lions’ most recent playoff win was after the 1991 season. Their previous one was in 1957, in the NFL title game. The Lions won championships in 1952, 1953, and 1957 but struggled ever since. They never made the playoffs in the 1960s, and did so just once in the 1970s, and twice in the 1980s. Running back Barry Sanders propelled Detroit to six playoff berths in the 1990s. Apart from the one 1991 playoff win, the team exited in the first round every time. After another prolonged playoff drought, QB Matthew Stafford helped Detroit make the playoffs in 2011, 2014, and 2016, but those seasons ended in wild card round losses as well.

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.

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.

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.

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.

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.

The Detroit Tigers missed their championship window in the early 2010s and are now in the midst of a rebuild. All-star players like Miguel Cabrera, Max Scherzer, and Justin Verlander powered Detroit to four straight postseasons from 2011-2014. Detroit made the World Series just once in that stretch, getting swept by the San Francisco Giants in 2012. Detroit’s record has declined every season since 2016, posting a 47-114 record in 2019 — the second worst in the Tigers’ 119-year history.

Prior to the 2000s, the Montreal Canadiens won at least one championship in every decade since the beginning of the NHL in the 1910s, earning 25 in total. But the Habs have not won a Stanley Cup since 1993. In fact, Montreal has not even made it to the Stanley Cup Finals since that season, only making it as far as the conference finals twice. The Habs used to go decades without missing the playoffs, but their most recent playoff appearance was in 2017 and ended in a first round loss.

Cincinnati’s “Big Red Machine” dominated baseball throughout the 1970s, making the postseason six times and winning two World Series. Their next postseason appearance in 1990 netted the Reds their fifth championship. Since then, Cincinnati has only won a single postseason series in four playoff trips — the 1995 NLDS. The Reds were swept out of the 2010 NLDS, beaten in the 2012 NLDS, and lost the 2013 wild card game. Since then, Cincinnati has never finished higher than fourth in the NL Central.

After an extended run of success, the Detroit Red Wings are now the worst team in the NHL. Detroit made the 25 straight postseasons from 1991-2016, winning Stanley Cups in 1997, 1998, 2002, and 2008. After losing in the 2009 Cup Finals, the Red Wings failed to make it past the second round in their next seven playoff appearances. The team that had once been the model of consistency then missed the playoffs in 2017, 2018, and 2019. Before the 2019-2020 season was interrupted, Detroit was by far the worst team in hockey. The Wings earned 39 points in 71 games. No other team had less than 62.

The New York Knicks won two titles in the 1970s and were consistent title contenders in the 1990s, making the playoffs each season from 1988-2001 and earning a spot in the NBA Finals in 1994 and 1999. All changed when James Dolan became owner in 2000. The Knicks’ front office has been in disarray, shuffling through nine different general managers since 2003. New York has just four playoff appearances, two winning seasons, and one playoff series victory since 2001.

The Cleveland Browns have made the playoffs just once this century, in 2002, when they lost in the wild card round. The Browns last won a playoff game in 1994, and they have never made the Super Bowl. This is a far cry from how the team started its NFL journey. After joining the league in 1950, coach Paul Brown led Cleveland to seven NFL Championship games in eight seasons, winning three. Running back Jim Brown helped the team make two straight title games, winning in 1964 and losing in 1965.