4. 2017: Eliminated in NLCS
Expectations were high for the Cubs in 2017. After finally winning the World Series in 2016, the North Siders were coming back with mostly the same roster as the year prior. Except now Kyle Schwarber was healthy, top prospect Ian Happ was ready to contribute and Albert Almora was poised for a larger role after center fielder Dexter Fowler departed in free agency.
The Cubs were never going to live up to the heights of 2016, but 2017 was still very successful. The team took home another division title after a 92-win campaign. The Bryant, Rizzo and Schwarber offense was fierce, backed by a supporting cast led by Baez, Happ and Contreras.
The team secured a spot in the NLDS, where they faced a fierce Washington Nationals team that featured back-to-back Cy Young award winner Max Scherzer. The Cubs were also able to overcome two starts from a prime Steven Strasburg, who shut out the Cubs in 14 innings while striking out 22 batters. The Cubs took the series three-games-to-two, with closer Wade Davis recording saves in all three wins. With a one-run lead in the ninth inning of Game 5 and the tying runner in scoring position, Davis struck out Bryce Harper to send the Cubs to their third straight NLCS appearance.
The Dodgers were on a World Series quest though and ended up taking care of the Cubs in five games. But it was still a fantastic accomplishment for this team to make three straight deep playoff runs for the first time since the early 1900s.
3. 2003: Eliminated in NLCS
After making the playoffs just three times over a 56-year period from 1946-2002, the Cubs fanbase was starved for a legitimate playoff run. Although they got that playoff run, it is one that will forever live in infamy and be listed at the heart of the team's 108-year championship drought.
But let's start with the team's regular season, an 88-win effort that was fueled by an elite starting rotation. 2001 first-round draft pick Mark Prior led the way with a 2.43 ERA over 211 1/3 innings pitched. Zambrano, Wood and Matt Clement all surpassed 200 innings as well, taking pressure off a bullpen that featured four arms with sub-4.00 ERA's.
The offense was again propelled by veteran slugger Sammy Sosa, who had spent the last decade-plus sending baseballs onto Waveland Avenue. After taking home just the third division title in team history, the Cubs upset the Atlanta Braves to advance to the NLCS, winning their first playoff series since the 1908 World Series.
Things continued to look promising after going up 3-2 in the NLCS against the Florida Marlins. But Cubs fans know all too well how all hell broke loose in Game 6. Prior started the game and pitched to near perfection for seven straight innings, striking out six with no runs and three hits. Chicago was six outs away from a World Series berth, but by the end of the eighth inning, the Marlins had scored eight runs.
This was the infamous Steve Bartman game, where the fan attempted to catch a foul ball that may have been in reach for left fielder Moises Alou to grab. We'll never know if he would have made the play, but we do know that Bartman received a mountain of unwarranted backlash. It wasn't his fault that Cubs shortstop Alex Gonzalez made a critical fielding error to load the bases. Or that Dusty Baker probably should have yanked Prior earlier than he did. Or that the Cubs went on to lose Game 7 the next day. In any case, many view this inning as the worst meltdown in team history, which says a lot for a team known as the Lovable Losers.
So why do I rank 2003 so highly? Well on paper, this was the closest the Cubs came to an NL pennant in nearly 60 years. They were right there and had the talent to win it all that season.