6. 2018: Eliminated in NL Wild Card Game
The vibes in Wrigleyville in 2018 were honestly pretty darn good. The team seemed ready to shake off the World Series hangover form 2017 and get back to work. The regular season was fantastic, with 95 wins under Maddon while the offense remained pretty solid.
Although Kris Bryant sat out a large chunk of the season with an injury, he was still productive while healthy with a .834 OPS and 126 wRC+. Anthony Rizzo, Wilson Contreras and Kyle Schwarber provided steady numbers throughout the season, but Javier Baez was the real story. The energetic infielder realized his full potential in his age-25 season, with 34 home runs, 40 doubles and a second-place finish in the National League MVP voting.
Unfortunately, the team's luck ran out in October. Although the 95-win regular-season effort was fantastic, the team found themselves tied with the Milwaukee Brewers after the regular season. A very rare 163rd game was held to break the tie. Interestingly, the Colorado Rockies and Los Angeles Dodgers found themselves in the exact same position, creating a sort of pre-postseason playoff round with seeding and home-field advantage on the line.
The Cubs lost their game and had to face the Rockies in the NL Wild Card game. It was a frustrating game that went into extra innings, and Chicago took a tough 2-1 loss to end their season. The offense simply could not score, recording just six hits and one extra-base hit over a stagnant 13 innings. Had they simply won one more regular season game, the team could have avoided the winner-take-all Wild Card game and perhaps things would have turned out differently if the Cubs had made it to the Division Series.
5. 2008: Eliminated in NLDS
The Cubs built upon their 2007 success and emerged as a powerhouse in 2008. Pinnella's Cubs finished with 97 wins, good enough for tops in the National League and their second division title in as many years. The team saw potent production across the board from heavy hitters like Derrek Lee (111 wRC+), DeRosa (121) and Aramis Ramirez (129). Catcher Geovany Soto won NL Rookie of the Year and other additions like Kosuke Fukudome and Reed Johnson gave the lineup a good balance of power, defense and speed.
The pitching staff was again led by Zambrano, Lilly and Ryan Dempster. The 34-year-old Dempster posted a career year (2.96 ERA) after converting back to a starting role. Future Cubs Hall of Famer Kerry Wood locked down the closer job, with 34 saves and a 3.26 ERA in 65 games.
But the postseason was again a similar story. One of the Cubs' most promising teams in the organization's history suffered another clean sweep out of the NLDS. The Dodgers outscored the Cubs in the series 20-6 while Dempster, Zambrano and Rich Harden each took the loss in their respective starts. It was a disappointing end to a fantastic season that marked the 100-year point since the team's last World Series title.
2008 ended up being the last hoorah of the Tribune era. The team was sold to the Ricketts family in July 2009 for $900 million, ushering in a new era for the organization. But many Cubs greats from yesteryear played pivotal parts on the 2008 team and it is certainly a fun time to look back on.