"Lovable losers" is a term that Chicago Cubs fans would probably prefer to never hear again. Unfortunately, there's only one way to really make it permanently go away.
The Cubs captured the NL Central crown in 2007 and 2008 thanks to a series of extremely aggressive acquisitions by former general manager Jim Hendry. While the organization had visions of ripping off a long run of success, it all came to a screeching halt after a roster that looked like it might be baseball's best won a disappointing 83 games in 2009. The Cubs sank further into the abyss, and Hendry was eventually fired during a 71-win season in 2011.