Cleveland Cavaliers, Basketball (2010-2011, 25 straight games)
The Cleveland Cavaliers in recent years were known as a top contender in the Eastern Conference but with the loss of LeBron James to free agency, the Cavs have hit hard times. They are currently in one of the worst losing streaks ever seen in professional sports and are only two more losses from holding that sole distinction. The catch is that they aren’t exactly playing bad basketball, they just can’t seem to close out games in the fourth quarter.
Pittsburgh Pirates, Baseball (1993-present, currently 18 straight losing seasons)
It’s hard to believe that the Pittsburgh Pirates used to be a powerhouse in the National League East and were contenders in three straight seasons in the 90’s. It’s especially hard to believe considering they haven’t had a winning season since they got rid of Barry Bonds back after the 1992 season. It just goes to show how important it is to have good ownership that is willing to spend and quality baseball people who know who to spend the dough on. Those are two things the Pirates are in desperate need of.
Tampa Bay Buccaneers, Football (1983-1996, 14 straight seasons)
Tampa Bay has had it’s share of losing notoriety throughout the years but the ultimate pits for them came between 83-96 where they had 14 consecutive losing seasons. During that stretch, they had three two-win seasons, one three-win season and one four-win season. The most glaring negative to come out of this time however, besides their bright orange uniforms, was that they traded away a future Hall of Fame quarterback. A little known guy that goes by the name of Steve Young.
Detroit Lions, Football (2008 season 0-16)
Arguably one of the worst franchises in the NFL, the Detroit Lions have fallen on some pretty hard times over the years. The kicker came in 2008 where they lost an NFL record 16 straight games. For those that’s counting, yes that’s every game that season. This dismal stretch of games cost their GM and their Coach their jobs, for obvious reasons, and unless the league expands to 18 games, will hold up as the worst NFL season for all time.
Tampa Bay Buccaneers, Football (1976-1977, 26 straight games)
The Buccaneers entered the NFL as a member of the AFC West in 1976 (then moved to the NFC Central in 1977) and proceeded to lose all 14 games of their inaugural season. Filled with determination and firm resolve, they came out in the next season and lost the first 12 games of the season before finally getting their first W in week 13. The bad news is that the teams, for this stretch, was the butt of comedian jokes across the lands. The good news, however, is that they no longer hold the distinct pleasure of having the worst season in the NFL, thanks largely to the league expanding to 16 game seasons and the futility of the 2008 Detroit Lions.