Jon Lester Signs with the Chicago Cubs for $155 Million


The Jon Lester sweepstakes has finally reached its conclusion and Major League Baseball may now resume its regularly-scheduled offseason.

The pitching market has been in gridlock while the baseball world waited to see where Lester would sign. Now that he’s inked his new six-year, $155 million deal with the Chicago Cubs, the rest of the dominoes can begin to fall for other big name starters like Max Scherzer and James Shields.

Lester was always going to be the one to set the market for free agent arms. He’s an experienced lefty with solid numbers, big game experience, and he’s survived the rigors of the American League East for the better part of the last decade.

Lester drew a lot of early interest from the big market clubs with money to spend and holes in the rotation. The Cubs, Boston Red Sox, and San Francisco Giants all showed interest in Lester the minute he hit the market. The Los Angeles Dodgers joined the fray in the last week with hopes of a late push to land the Southpaw.

Many of the clubs tried to make their sales pitch as personal as possible for maximum impact on Lester and his agents.

Red Sox owner John Henry reportedly flew to Lester’s home near Atlanta late last week for a one-on-one meeting with Lester in an attempt to sway Lester to return to Boston and – potentially – to sweeten the offer the club already had on the table.

San Francisco’s All-Star catcher, Buster Posey reportedly joined Giants brass and manager Bruce Bochy on a trek to Georgia to meet with Lester last week. The meeting, particularly Posey’s impact, was dubbed “really impressive” by those in attendance.

Ryan Dempster, who recently retired as a member of the Cubs and joined the club’s front office, reached out to his former teammate to convince him how great it is to play in Chicago.

Personal touches are nice, but Lester made it pretty clear in recent days that he was holding out for big money. There is even some speculation that he was purposely drawing out negotiations with the intent of pushing the bidding up beyond $150 million.

As it turns out, when you’re really, really good at what you do and supply is limited, that number doesn’t seem so crazy to baseball executives. It was widely reported that Lester received similar six-year, $150 million offers from all four suitors before the end of the first day of the Winter Meetings.

Ultimately, that proved to be untrue with the Cubs winning his services with their six-year, $155 million offer, the Red Sox reportedly offered six-years, $135 million, and the Giants are believed to have offered six-years, $150 million and were reportedly willing to go as high as seven-years, $168 million if Lester indicated that’s what it would take to get it done. Any offers made by the Dodgers, whose interest seemed to be more of a smokescreen than anything concrete, aren’t know at this time.

The news began to break late Tuesday that both the Giants and Dodgers were out of the running and it had become a two-horse race between the Red Sox and Cubs.

Needless to say, Lester has been the guy at the top of everyone’s wish list thus far. Given his career-best year in 2014, this shouldn’t have been a shock to anyone. Lester, 30, was 16-11 with a 2.46 ERA, 1.10 WHIP, and a 4.58 K/BB ratio that eclipsed his previous career-high of 3.52 set back in 2009.

Lester also added to his value when he proved he was able to adapt to life outside of Fenway Park. The lefty went 6-4 with a 2.35 ERA in 72.2 innings for the Oakland Athletics after he was acquired in a blockbuster trade deadline deal in exchange for outfielder Yoenis Cespedes.

In his nine year career Lester has accumulated 116 wins, a 3.58 ERA, a 1.28 WHIP, and a 2.67 K/BB ratio. He’s a three-time All-Star and has finished in the top four in Cy Young voting twice. Now he’s a Cub.

lester-cubs2In choosing to Chicago, Lester immediately moves to the front of a hodge-podge rotation that will include some combination of the recently re-signed Jason Hammel, Jake Arrieta, Kyle Hendricks, Travis Wood, Tsuyoshi Wada, Felix Doubront, Jacob Turner, and Edwin Jackson.

While this is not the most imposing rotation, there is a lot of room for growth and improvement.

Arrieta had a breakout year, Wada showed signs of holding down a middle-of-the-rotation slot, and both Hammel and Wood have shown flashes of success plying their trade at Wrigley Field in the past. Turner was once a top prospect and Jackson, every now and again, can put together a solid season.

In addition to the in-house options, one has to think that after making a commitment of this size to land Lester, the Cubs aren’t afraid to go all-in and pursue another big arm on the market.

James Shields, Brandon McCarthy, and Ervin Santana have all had their names kicked around as potential second-tier options.

They might also explore trades for Jordan Zimmermann, Johnny Cueto, Mat Latos, Cliff Lee, or Cole Hamels if they’re willing to deal some of their prized prospects to bolster the front of the rotation.

This move – coupled with the acquisition of catcher Miguel Montero on Tuesday – makes the Cubs a better team than they were coming into the day, but it’s hard to see this move being enough to make them a contender right away.

The club has one of the most enviable collections of young talent in the game, but short of them all peaking very early in their careers, the Cubs are probably still a couple of years away from being viable contenders.

At the very least, Jon Lester figures to be the first of many moves that will turn this rebuilding club into a legitimate pennant hopeful, likely, much sooner than Theo Epstein and Jed Hoyer had originally envisioned.

It’s clear that Epstein and Hoyer still have more work to do this offseason, it’s safe to say that they are quite happy to have landed their ace and I’m going to go out on a limb and assume Lester is quite happy with the $155 million he’ll be collecting over the next six years.

As for the Red Sox, Giants and Dodgers – it’s back to the drawing board for all three clubs as they look to continue improving for the 2015 season.

About Jeremiah Graves

I am a professional library dude, a cheeseburger enthusiast, a wannabe writer, a slow-pitch softball center fielder, an avid hunter (of churros), a cat-person, and — hopefully — one of your two or three favorite Iowans.
This entry was posted in Baseball, Boston Red Sox, Cheap Seat Chronicles, Chicago Cubs, Free Agency, Jon Lester, Los Angeles Dodgers, MLB, MLB Winter Meetings, New York Yankees, Oakland Athletics, San Francisco Giants, World Series, Yoenis Cespedes. Bookmark the permalink.

8 Responses to Jon Lester Signs with the Chicago Cubs for $155 Million

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