Originally Posted on the Previous Iteration of Baseball.FYI by Chris Murphy
Between 1946 and 2014 the Chicago Cubs made the playoffs a whopping six times. This included a heartbreaking NLCS collapse against the Padres in 1984, the Steve Bartman game in 2003, and back to back first-round sweep exits in 2007 and 2008. Let’s just say things rarely went well on the Northside of Chicago, and when they did, it usually ended in catastrophe.
In a much shorter six-year span between 2015 and 2020, the Cubs played October baseball five times (barring an epic late-season collapse this year.) At the very least that run will include three NLCS appearances, one National League pennant, and a curse-breaking 108 years in the making World Series title.
So what changed between then and now? Jon Lester.
Ok, ok, maybe that wasn’t the only thing but it was a big one. When Lester signed with the Cubs in the 2014 offseason the team was coming off a 79-83 finish, their 5th losing season in a row. While the money was surely enticing (the Giants actually offered him more), and the Theo Epstein connection made Chicago feel a little more like home, Lester took a chance on an up-and-coming team that had proved little and generated a lot of hype.
This was an established big time pitcher willing to immediately step into a leadership role for a franchise with a horrible history and room to grow.
The day Lester signed with the Cubs the league was put on notice. As a Sports Illustrated cover immortalized forever, the team’s odds to win the World Series immediately shifted from 50 to 1 to 12 to 1.
While Jake Arrieta emerged as an ace, Anthony Rizzo developed into a clubhouse leader, Javy Báez became El Mago, and Kris Bryant took the league by storm, Lester held up his end of the deal.
The workhorse put up 200 innings in both of his first two years in Chicago and came pretty close to that mark for the next three. These efforts doubtlessly contributed to the bullpen success of guys like Pedro Strop, Wade Davis, and Hector Rondon.
Suddenly, the Cubs were consistently winning 90+ games a season, topping out at 103 during the magical 2016 run.
Now, free agents wanting to taste the postseason looked to Chicago as a top tier landing spot. Jason Heyward left the arch-rival Cardinals for a shot at that glory and Yu Darvish found a home after his disastrous 2017 World Series.*
While the Craig Kimbrel experience has been an up-and-down ride for Chicago, his signing is another example of how the perception around the Cubs shifted quickly after Lester joined.
In 2016, Lester came through when it mattered, sharing NLCS MVP honors with Javy Báez and locking down a crucial World Series game 5 victory when the team sat on the brink of elimination down three games to one.
In the ultimate nerve-wracker, game 7 of the World Series, Lester entered the game in relief and overcame a curse like 2-run wild pitch to contribute 3.1 innings and four strikeouts in that long awaited victory.
Lester’s postseason statistics speak for themselves. The guy is simply nails when the season is on the line.
As the years went on, Jon Lester moved down the rotation as his ERA grew. But the dreaded long-term-signing back-end-drop-off never felt like that of other big name free agents (looking at you Albert Pujols). Lester was still a significant contributor who fans wanted on the mound in big moments.
Ultimately, the Cubs could not possibly have asked Lester for anything more. He was the perfect piece at the perfect time. It’s hard to doubt that in addition to the play on the field, Lester’s playoff experience and even keel kept a young team focused when it could have fallen off.
The chain of events set in motion by #34 taking a chance on a down and out franchise lead to one of baseball’s, if not sports in general’s, biggest moment of the century.
Lester’s decision in 2014 marked the start of a new era of baseball in Chicago. An era of leadership, of playoff appearances, and of winning. With much of the team’s core set to become free agents after 2021, his departure could mark the beginning of the end.
So, with his future with the team uncertain (although he has expressed interest in returning), Cubs fans should take a moment to thank Jon Lester. If this is it, it was quite a ride.
And hey, who knows what the 2020 postseason might bring.