Is Jon Lester Really Worth What He’s Reportedly Being Offered?

Sep 30, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher Jon Lester (31) throws a pitch against the Kansas City Royals during the first inning of the 2014 American League Wild Card playoff baseball game at Kauffman Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports
Sep 30, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher Jon Lester (31) throws a pitch against the Kansas City Royals during the first inning of the 2014 American League Wild Card playoff baseball game at Kauffman Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports

Jon Lester is going to get paid, but is he worth it?

According to numerous media reports this week, and last, Jon Lester is going to be offered The Big Bucks. According to sources obtained by CBSSports.com’s Jon Heyman, the Chicago Cubs have offered Lester a contract in the vicinity of six years, $138 million.

At the same time, there are rumblings that Boston has offered a similar deal with a few pennies less—six years, $130 million—to return to Boston, who traded him for Yoenis Cespedes at the July 31 trade deadline.

That potential “reunion” was hinted at even when Lester was traded away in July. The southpaw is revered in Boston first because of his class and triumphant spirit over cancer, which was on full display to the New England baseball fan back in September 2006. Lester was finishing his rookie campaign only to find out at the beginning of the season’s final month that he had lymphoma.

Credit: Ed Szczepanski-USA TODAY Sports
Credit: Ed Szczepanski-USA TODAY Sports

But the earliest form of “Boston Strong” exuded by Lester, in beating cancer, is only one of two primary reasons that he is so revered. He, of course also had an amazingly successful run on the mound from 2007 to mid-2014, pitching the clinching game of the ’07 World Series for Boston and then going on for his career to pitch 11 postseason games with 1.97 ERA, including three World Series starts where that thing was 0.43.

Thus it’s only natural that Lester is beloved in Boston. And it makes sense that key figures in the Boston golden age, which more or less began in 2004—namely Theo Epstein, now running the entire baseball operations for the Chicago Cubs—would be all in on the lefty, who turns 31 in January.

But there’s a seemingly very relevant question that no one seems to be asking. Is Jon Lester really worth six years and upwards of $20 million per year (some have suggested that when the bidding is finally completed it could escalate to around six years, $150 million)?

At first glance, I am tempted to say no. First off, at the completion of his contract he is going to be in the back half of his thirties. That is substantial. Plain and simple, few pitchers can sustain success that deep into their career.

You don’t find pitchers who remain as successful as he’d need to be to justify that contract until you start looking at all-time greats. And frankly, Lester does not qualify on that list—not yet anyway. As of now, he’d have to be considered the third best southpaw in the game.

Clayton Kershaw has cemented his status as the greatest regular season pitcher of this current generation. Then this past postseason Madison Bumgarner made a legitimate case that he is the best postseason pitcher maybe ever (if for no other reason than he pitched the final five innings in Game 7 of the World Series with his team clinging to a one-run lead with only two full days of rest from his Game 5 start).

It’s like this: You’ve been dating someone who you legitimately like a lot, but after a month, maybe two you realize this person’s great but…and the “but” is always that you know beyond a shadow of a doubt that there’s someone better out there—someone prettier or more handsome, someone who is smarter or funnier or more successful or plainly that you would just get along with better.

In comparison to Kershaw or Bumgarner, Lester is that person you’ve been dating. You really like him, and you know the two of you could be pretty darn happy for a while. But do you really want to settle down with him and raise a family with him (in the metaphor build an entire pitching staff around him)?

Jul 15, 2014; Minneapolis, MN, USA; American League pitcher Jon Lester (31) of the Boston Red Sox throws a pitch in the second inning during the 2014 MLB All Star Game at Target Field. Mandatory Credit: Scott Rovak-USA TODAY Sports
Jul 15, 2014; Minneapolis, MN, USA; American League pitcher Jon Lester (31) of the Boston Red Sox throws a pitch in the second inning during the 2014 MLB All Star Game at Target Field. Mandatory Credit: Scott Rovak-USA TODAY Sports

It may speak more to the depth of the Boston squads from 2007 to 2013, but Lester was never the unquestioned Ace, the guy who absolutely gets the ball Game 1 And Game 7 of the World Series.

He was a great pitcher, a guy whose stock rose undeniably as a result of the 2013 postseason when he was basically Madison Bumgarner before there was a Madison Bumgarner (now a noun which could be used as a verb; “to Madison Bumgarner is to pitch lights out throughout an entire postseason and singlehandedly win the World Series for your team”).

Here’s what it comes down to in the perspective of this writer. Lester has been lights out on postseason teams which featured incredible offenses (2007 Boston, 2013 Boston). There is no question he pitched incredibly well in most, if not all of his postseason starts in Boston.

But then, in the one-game playoff to enter the Divisional round this past October with Oakland, Lester wasn’t so great. In fact, his entire time in Oakland, he wasn’t so great. Looking at common metrics, you’d say that he was.

But his park adjusted ERA (ERA+) rose from 154 in Boston to 159 during his time in Oakland. And his FIP (Fielding Independent Pitching) rose more dramatically from 2.62 to 3.13, according to Baseball-Reference.com.

In other words, Oakland’s mediocre defense could not be blamed for the rise in Lester’s numbers. In fact, his ERA actually went down in Oakland. But as the numbers above show, it had more to do with his surroundings than it did his own improvement.

This leaves us with the key question: If you’re the Cubs and playing half your games in Wrigley Field do you really want to rely on a guy who proved that pitching outside of Boston he’s really good, but not great? And pay him the kind of money you’ve reportedly offered?

I don’t question Epstein and the Cubs’ brass, other than to say it goes a bit against what they had been saying up until this offseason. It seems they were deflecting questions about acquiring a top notch staff ace, and now they’re ready to throw money at the first shiny toy in front of them.

These are questions worth asking. I don’t have the answer. Maybe Lester is that good. Maybe he is worth it for Chicago or Boston or some other team.

At the end of the day I’m just glad it’s not my money or my job on the line.

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