#4: 2008 Cubs
One might call this team the last truly huge disappointment in Cubs history before Theo Epstein arrived to finally change it all. After a tough 2007 season that saw them swept from the playoffs, it felt like 2008 might be a year of vindication for the Lovable Losers. They won 97 games. Lou Pinella was Manager of the Year and the roster featured an uncanny eight All-Stars headlined by slugger Alfonso Soriano and Rookie of the Year Geovany Soto.
There were warning signs though that the team was starting to crumble late in the year. They finished with a rough 12-12 record in September including losses in four of their final six games before the playoffs. Sure enough they came out flat in the NLDS against the Los Angeles Dodgers, a team that finished just six games over .500. The Cubs margin of defeat in that series was 20-6, losing both games at Wrigley Field 10-3 and 7-2. Just bad all around.
