2. 2015: Eliminated in NLCS
After president of baseball operations Theo Epstein took over in 2011 and took the time to assemble a contending roster, 2015 was the first time in the Ricketts era the Cubs were ready to compete. The team also thrived in a particularly difficult year in the NL Central. Despite winning an impressive 97 games, the Cubs finished third in the division behind the St. Louis Cardinals and Pittsburg Pirates.
But the team had new manager Joe Maddon leading the way, whose relaxed, vibes-based leadership style proved to be a successful approach for the young team. But great performance on the field also played a huge factor. Rizzo continued his cornerstone offensive production and Fowler's leadoff abilities helped set the table for exciting young rookies like Bryant and Schwarber, who were emerging as the best hitters on the team.
But the team's real weapon was ace Jake Arrieta, who was in the middle of one of the greatest starting pitching runs in baseball history. The bearded right-hander was also the key to the team's postseason success. Because of the third-place finish, the Cubs qualified for the NL Wild Card game. A game where Arrieta masterfully outdueled Pirates' ace Gerrit Cole and dominated the Bucs lineup with 11 strikeouts in a complete game shutout.
The success continued in the NLDS, where the Cubs had a date with the Cardinals. The Cubs spent years watching the Red Birds succeed in October and win two World Series in recent years (2011 and 2006). But 2015 saw the Cubs finally stick it to their longtime rival in the playoffs. The Cubs won the series 3-1 behind their potent offense, which included a booming home run off the scoreboard at Wrigley from Schwarber.
The magic ran out in the NLCS when they ran into a buzzsaw in the form of the New York Mets, whose starting rotation of Jacob deGrom, Matt Harvey, Noah Syndergaard, and Bartolo Colon contributed to another postseason sweep for the Cubs. Although they were denied a pennant, the Cubs went into the offseason feeling good about their roster and this season ended up being the first of several playoff births for the team in the 2010s.
1. 2016: Won World Series
Epstein got to work bolstering his 97-win squad in 2015 by signing some key veterans to help mentor his younger players. Ben Zobrist, John Lackey and Jason Heyward were the key additions to a team that dominated the league in 2016. The team cruised to a hefty lead in the NL Central early on and never looked back, finishing with 103 wins and 58 losses, the best record in MLB that year.
Bryant turned in a season for the ages, taking home the National League MVP after crushing 39 home runs, driving in 102, with a 148 wRC+ and 7.5 fWAR. The team featured 10 players with a WAR above 2.5 in 2016, including four members of the starting rotation. Jon Lester and Kyle Hendricks owned the two lowest ERAs in baseball during the regular season, flanked by stellar campaigns from Arrieta (3.10 ERA) and Lackey (3.35 ERA). The dominance was convincing enough for Epstein to send top prospects to the New York Yankees for ace closer Aroldis Chapman, who cemented the bullpen as a lockdown unit.
After a historic regular season, the Cubs broke their 108-year World Series curse, which is still the longest drought in MLB history. The playoffs were full of memorable moments, like a four-run rally in the ninth inning against the San Francisco Giants in game 4 of the NLDS. The Cubs fought through a tough Dodgers team in the NLCS, surviving back-to-back shutouts in starts from Clayton Kershaw and Rich Hill respectively. Chicago stormed back to win three straight games, clinching the series behind 7 1/3 shutout innings from Hendricks and a save by Chapman.
After securing their first NL pennant since 1945, the Cubs again overcame a deficit in the World Series against the Cleveland Indians. After going down three games to one, the North Siders won three straight and competed in one of the most nail-biting Game 7s ever played. The contest featured a game-tying home run off Chapman, a rain delay speech, and eventually a Cubs rally in extra innings which proved to be enough to take home the Commissioner's Trophy.
This is hands-down the best season the Chicago Cubs have ever played in the modern era of baseball. They reached 100 wins for the first time since 1935, rode a convincing lead to a division title, and orchestrated multiple playoff comebacks to break their infamous streak of losing.