Red Sox

Jon Lester Has Plenty in Common with Andy Pettitte, and You Can Bet the Yankees Know It

I can’t be the only one who watched that smarmy Hat Tip to Derek Jeter commercial (sweet mustache, MJ) and wondered whether a certain pitcher he’s facing might end up following him in pinstripes next season.

I’m generally not big on the if-the-Sox-don’t-sign-him-the-Yankees-will scare tactics — some New York writers are already suggesting the Yankees could shop Jacoby Ellsbury 60 percent of the way through the first year of his seven-season deal.

Usually, the Yankees should only be a cursory consideration when it comes to the Red Sox’ personnel decisions. The best practice is to do what is best for their franchise without paying much heed to which players their rivals might covet.

But the troubling idea of Lester changing sides in this rivalry is at least something that has to be considered, not just because it’s something we always consider, but because it makes sense should the Red Sox foolishly allow him to get to free agency.

The Yankees need Jon Lester. I hate being an alarmist about this, and I even hold out hope that something between the 30-year-old lefty and the Red Sox gets done during the All-Star break. It would be a swell outlier of good news in this maddening 2014 season, which so far has been the bizarro version of ’13.


With occasional exceptions, the Yankees tend to get what they both want and need. Again: they need Jon Lester. Masahiro Tanaka is their Matt Harvey, for reasons thrilling and sad. CC Sabathia looks cooked. Ivan Nova is recovering from Tommy John surgery. Hell, they’re one more injury from giving Tommy John himself a start or two.


(Joke you surely see coming: Most of Tommy John’s parts are 71-years-old, but his elbow is just 40! I will not apologize.)

Lester would be an ideal fit right now and going forward — but he also draws easy similarities to a Yankees star who threw his final pitch last year. The Replacement-Level Red Sox Blog featured a thoughtful post recently comparing Lester to some of his most similar pitchers through age 29, per baseball-reference. No. 2 on that list was a pitcher who has a similar pedigree to Lester — a sturdy, durable lefty who may not be the hardest thrower but certainly has enough velocity, features a killer cutter, and tends to deliver in big moments.

You think the Yankees would like another Andy Pettitte?

The comparison matters for reasons beyond the obvious style and skill similarities. It doesn’t take much sleuthing to identify any concerns the Red Sox may have about paying Lester long-term. Lucrative contracts for players in their 30s tend not to be wise investments. That’s especially true for pitchers.

Such collateral-ligament carnage this season — whether to budding aces like Tanaka and Jose Fernandez or a presumed rubber-armed veteran like Bronson Arroyo — has served as a repeatedly cruel reminder that a pitcher’s future is at risk every time he releases the baseball.

Some survive better than others, and there is increased value in those who do. Lester has pitched at least 191 innings every season since 2008. This year, he is on pace for his sixth season of at least 200 innings. He is also tracking toward having the best season of his career. As measured by adjusted ERA, here are the top five seasons of his career:


Lester’s best five seasons are fairly similar to Pettitte’s top five:


Now look closer. Anything jump out at you? How about this? Three of Pettitte’s five best seasons came after age 30 — and it’s four of six if you include his 2012 season, when he had a 148 OPS+ in 12 starts at age 40.

Yes, two of those seasons came in the National League with Houston, and he did admit to using HGH to recover from an elbow injury in 2002. We’ll never really know if it played a greater role in his longevity, but we do know this:

Jon Lester, a pitcher similar to Pettitte in most every meaningful way, has improved in relevant ways as he’s entered his 30s. He’s had one lousy season, but the only thing to prevent him from taking the mound every fifth day was bleepin’ cancer. No pitcher is a certain bet to thrive into his 30s. But if I’m taking that bet, I’m putting that money on Lester.

Speaking of money: Pettitte made $105.75 million in salary from age 31 until the end of his career. For that, he provided $134.6 million in value.

Forget four years and $70 million. If the Red Sox want to keep Lester, a well-above average pitcher who doesn’t miss his turn and delivers when you need him most, the next offer should be in the range of $120 million.

Based on what Pettitte was worth for so many years, it’s more than fair. Hell, it may even be a discount.


Yes, sure, there’s risk. There always is with any pitcher, any player over 30.

This is one worth taking. I do not know how they would replace him.

And this is not a scare tactic, but a legitimate baseball fear: if the Red Sox do not take that risk, a certain team that knows precisely what a pitcher so similar to Lester is worth gladly will.

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