Chicago Cubs: Was Jon Lester the right choice?


When Jon Lester turned down the initial offers made by the Boston Red Sox -most Cubs fans started to think about the idea of possibly the 2015 season with Jon Lester wearing Cubs pin stripes.  The whole season was a kind of “wait and see” because at no point during the season did anyone expect the Cubs to contend in 2014.  Because of that, it gave us Cubs fans a whole year to dream up of “what could be” once the season was officially over and the winter meetings started.

The free agency list this off-season was a better one than what we have seen in a few years as far as starting pitching was concerned. Going into this off-season it was no secret that Theo Epstein and Jed Hoyer had their sights set on one of the key free agent arms-question was what one was going to be pursued the most by the Cubs? With Jon Lester, Max Scherzer and James Shields being the top names available, the question then was which one was the best fit for the Cubs.

Scherzer, coming off another great season with Detroit had been linked to rumors of wanting a record-breaking contract.  Considering who Scherzer’s agent is, Scott Boras, it wasn’t out of the realm of possibilities that he would see that kind of money.  While his stats were there to warrant that kind of attention, it may also have scared off a lot of teams.  It was rumored that Scherzer turned down an offer from Detroit before the 2014 season that was worth $144 million over 6 years.

Jan 21, 2015; Washington, DC, USA; Washington Nationals pitcher Max Scherzer walks onto the stage prior to an introductory press conference at Nationals Park. Mandatory Credit: Geoff Burke-USA TODAY Sports

For a former Cy Young winner (2013) and finishing in the top 5 in the American League in strikeouts in three consecutive seasons; Scherzer would be considered an ace on any team. While I think the Cubs would have liked to have signed Scherzer, I don’t think he was ever truly considered their top choice.  I think the money was just too much for the Cubs who are still finalizing their plan and picking up what could have been a $200 million contract would compromise that plan.

James Shields I thought was for sure on the Cubs radar.  He was a power pitcher who was a key part of the success of the Kansas City Royals. But most importantly he was a former player of Joe Maddon.  While Shields may not have been as hyped as Lester or Scherzer, you cannot take away from what he brings to any team he has been with.  He’s a workhorse-averaging over two-hundred innings in his career.

What worked against Shields was for one his age.  Not many pitchers who’ve logged the amount of innings over their career have been able to stay that good for that long.  We have seen what that kind of work has done to similar pitchers as Shields.  Best and most recent example is Justin Verlander.  Since Verlander turned thirty years old, the innings haven’t gone down but his production has.  Shields, now at the age of thirty-three, could at any time start to show that same wear.

Oct 26, 2014; San Francisco, CA, USA; Kansas City Royals starting pitcher James Shields throws a pitch against the San Francisco Giants in the first inning of game five of the 2014 World Series at AT&T Park. Mandatory Credit: Elsa/Pool Photo via USA TODAY Sports

Considering Shields age, this off-season was going to be his first and probably only real chance at a big pay-day. Because of that, you know his agent was looking for most money and the longest contract.  After working hard to get the Cubs out of a few bad contracts that were signed by previous management, it would have made no sense for Epstein or Hoyer to sign another long-term contract to an aging veteran.

Jon Lester was immediately linked to the Cubs as soon as Epstein and Hoyer came aboard the Chicago Cubs management.  Myself being from New England, I can tell you that all Red Sox players that were closely tied to Epstein were rumored to be targets by the Cubs.  Jon Lester was number one on that list for many.

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Once Lester turned down the offer made by the Red Sox, the news media started to speak of rumors and grumblings about how it was considered a “low ball” offer by the Red Sox.  It was only a matter of time before those rumors of Lester to the Cubs would heat up.  Lester signing to the Cubs gave them everything they were looking for.  The right age, the right price, the right player.  A proven winner with Boston, one of the better post-season pitchers in baseball today, and a relationship with Epstein from back in Boston.

It was really the perfect match.  With the contract that was signed, it still gives the Cubs the financial flexibility to make more moves.  The 2016 free agent pitcher market is going to be one that all teams are already getting their books in order for.  I’d imagine the Cubs will be one of the main teams that will be involved with the biggest and best names available.

If the Cubs would have signed Scherzer early on, the price could have been close to that $200 million mark-if that happened, the Cubs would not be involved in next years free agent market.  If the Cubs would have signed Shields after the signing of Lester, it would compromise what could be done next year.  I know we are all in a “win now” kind of state and hate that term “next year”, but it really needs to be said.  While I can see the Cubs fighting for the wild card spots, I can see the Cubs contending and possibly winning with another starter being placed next to Lester.