Is Jon Lester Really Worth 6 or 7 Years and More Than $140 Million?

Let me begin by saying that I think Jon Lester is a great pitcher and, by all accounts, an awesome guy who could fit right in with a team full of young players as a top-of-the-rotation arm. But my main question is: Will the team that signs him regret handing him a 6 or 7 year deal worth north of $140 million?

When Theo Epstein was first hired in 2011, he said this about free agent signings: “The key is to pay for future performance, not past performance.” Is handing Jon Lester an extremely large sum for the next 6 or 7 years paying for past performance or future performance? If the deal ends up being for 6 years, is any team going to feel great about paying a 37-year-old pitcher $20-25 million?

The Numbers

Lester, who will be 31 years old by Opening Day 2015, was selected in the 2nd round of the 2002 draft by the Red Sox and spent his entire career in the Boston organization, until he was traded mid-season to A’s in a deal for Yoenis Cespedes.

He has amassed a 116-67 record with two World Series rings and three All-Star appearances and has finished in the top 5 in Cy Young voting twice. Lester has accumulated 1680 innings pitched (including 84 postseason innings). Over his 9 years in the Bigs he has totaled 35.4 WAR, with most of that coming over the past 7 years, during which he averaged 4.8 WAR.

This past season would be considered one of his best years as a pro. He set new career lows for ERA (2.46) and BB/9 (1.97) and had his 2nd-best xFIP (3.10), all while staying above his career average in K/9 (2014: 9.01, career: 8.22). Lester’s 6.1 WAR was second in his career only to the  6.2 he put up in 2009.

Up to this point Lester has been very healthy; since becoming a fixture in the Red Sox rotation in 2008, he has not started fewer than 31 games in a season. With that in mind though, he has been ridden pretty hard as pitcher and has logged over 200 innings in 6 of the last 7 years.

Based off of these numbers, would the Cubs be paying for Lester’s previous body of work or for his projected future performance? An even better question might be: will Lester be able to keep this kind of success going as he moves into  his 30’s?

Two Reasonable Comps

Baseball Reference listed some comparable pitchers through their age-30 season, interesting names like Tim Hudson, Andy Pettitte, and even Freddy Garcia. I like the Hudson and Pettitte comps quite a bit because they both had relatively healthy runs with a season here or there impacted, but not fully lost, by injury.

For comparison’s sake, let’s say that Lester signs a 7 year deal. What kind of value can the team that signs him hope to derive during that stage of his career? I submit to you Tim Hudson and Andy Pettitte as examples of what could be with a long-term deal for Jon Lester.

Note: both of these pitchers have or had careers that stretched more than 7 years after turning 31, but I am focusing on just the time frame of Lester’s presumed contract.

  • Tim Hudson
    • Compiled 86-51 record, 3.32 ERA, 5.7 K/9 (career avg 6) and 2.5 BB/9 (career avg: 2.6)
    • Averaged 26 starts and 170 IP, including 2008-2009 (TJ surgery) and 2013 (broken ankle)
    • Earned around $75.5 million over these 7 seasons
  • Andy Pettitte
    • Compiled 101-65 record, 3.88 ERA, 7.1 K/9 (career avg: 7) and 2.6 BB/9 (career avg: 2.9)
    • Averaged 31 starts and 192 IP and won 21 games as a 31-year-old for the Yankees in 2003
    • Made around $80 million during these 7 seasons

These are what I could consider “best case” scenarios for Jon Lester’s career. Neither guy listed above was a liability to his team during the given period. Each had some elbow injuries, were able to bounce back and have productive years after the age of 31. You can combine their salaries and come pretty close to what Lester is going to get for the next 6 or 7 years in his deal.

Granted, the economy of the game has changed and there is more money than ever before available to teams due to increased revenue streams, better attendance, and huge TV contracts. I have always considered myself to be in the “well it isn’t my money” camp, so I don’t truly care what Lester gets paid. I just would hope it doesn’t handicap the Cubs later on down the road, not that it should.


  • Lester has been extremely healthy over his career and by all accounts has a very easy delivery that should hold up well.
  • The NL Central is strong, but not as strong as the AL East or AL West.
  • Weaker lineups due to lack of the DH.
  • Solid foundation to the rotation and would fit in nicely if the Cubs acquire more arms down the road.
  • Epstein and Hoyer have a history with Lester, drafted him, developed him and know what type of character he has; a point that I don’t think should be discounted.
  • He only costs money, no compensatory picks or trades required.


  • The enormous in both money and years will carry the expectation that he remains both productive and healthy for the long haul.
  • The team that signs Lester would be paying him for his past performance and not so much for his future performance.*
  • While comps were good after they turned 31, I don’t think you would look at their performance and think they should have a $20-25 million salary.


Okay, so not a lot of cons to signing Lester to a huge deal, aside from the fact that pitchers his age are no sure thing to continue success for that long a term. I do think the things that really tip the scale for me are the facts that the front office is familiar with him and he only costs money. No loss of picks or prospects is very valuable.

With the Winter Meetings upon us, a decision should be coming pretty soon. I will not be crushed if the Cubs don’t sign Lester, if only because there are so many other options out there. Even so, I say go for it; but front-load the deal as much as possible to pay for future performance (as in the first 3 or 4 years) instead of rewarding the past.


*I do think the first 3 years of the deal will probably fair for both sides, but it is the last 4 years at $20-25 million each that are in question.

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