Red Sox

Seven Thoughts on Jon Lester While We Wait to Find Out Where He Will Pitch


The number of the day, kids, is seven. Seven-minute abs. Seven (at least) false Jon Lester-is-signing-with-[blank] rumors on Twitter. Seven years (we suspect) on his new contract. And seven things for us to think about while he considers where he’ll pitch the next several years …

1. Is there a specific salary threshold he wants to achieve? Actually, I think there are two possibilities at play here, and one of them will ultimately be how this all plays out.

Either he has a specific number in mind — I’d guess $150 million gets it done with either the Red Sox or the Cubs, with the Yankees always lurking. It still would not surprise me whatsoever if they come out of the woodwork with a seven-year, $175 million deal.

Or, theory No. 2: Lester and his agents have already decided to return to Boston but are being deliberately patient and thorough in a quest to make sure they make the Red Sox nervous and thus get every dollar out of them that they can before committing.

2. What in the name of Tuffy Rhodes were the Red Sox thinking in the spring? They can say four years and $70 million was intended as a starting point. They do say it. Maybe it even was. But that approach looks more ridiculous by the day.

The Red Sox had to know in the spring that if Lester resembled the superb pitcher in 2014 that he was in ’13 — and has been for most of his career — that offer was going to look like a disingenuous attempt for a 40-percent discount, minimum, starting point or not.


Lo and behold, that’s what it looks like right now. They’re lucky he liked it here so much, or he might have been insulted enough to say, “You had your chance. I’m gonna go pitch for Theo now.”

3. Are we overrating him? I really don’t think so. For a long time I thought of him as a very good No. 2 starter, maybe a 1A. But he never had the electrifying stuff or huge strikeout numbers of the select few we do consider true aces.

I mean, I don’t think anyone is comparing him to Clayton Kershaw — at least, the regular-season version of baseball’s best pitcher and the chief current reminder of how brilliant Pedro Martinez was in his heyday. Certainly no one in his right mind would do such a thing, though I suppose you could see Scott Boras making exactly that case if Lester were his client.

While Lester had some exceptional seasons — from 2008-10, he was never worse than 33 percent above league average — I began looking at him as a true ace perhaps at the same time you did. That, of course, is October 2013, when if not for David Ortiz’s puny 1.948 OPS in the World Series, Lester would have been the easy choice for Most Valuable Player.

Oh, and 2014 ended up being the best season of his career by measures conventional (2.46 ERA) and advanced (155 ERA+). He’s an ace, and he will be for a while.

4. He has incredibly appealing options. The consensus of Red Sox fans seem to want Lester back at any semi-reasonable price, which means if he doesn’t come back, there’s going to be a disappointed majority around here that may unfairly affect how he is perceived.


There will be caterwauling about the hometown discount thing. But I don’t know how we could blame him for leaving. If he signed with the Cubs — well, that’s an incredible city, he knows and trusts the front-office personnel, the roster is bursting with young talent, and he can seriously focus on his quest for his first big-league hit (he’s current 0 for 36).


5. Then there’s San Francisco. We know why the Giants are appealing; we’re reminded of all the reasons every other October. Can’t blame anyone for wanting to play in that city, in that ballpark, for that manager.

My question is this: If Lester chooses the Giants, then they go out and sign Chase Headley to replace Pablo Sandoval at third base, should Red Sox fans be envious of what ended up being behind Door No. 2?

I like the Sandoval signing, though NESN may have me rooting for the extinction of the panda before April is even over. But all things being equal, I’d prefer Lester to Sandoval … let alone Lester and Headley.

I probably should have also mentioned that playing for that general manager, Brian Sabean, can be pretty rewarding too. At least in those odd-numbered years.


6. He’s the best lefty the Red Sox have had in ages. To have seen a lefthanded pitcher who had a better career for the Red Sox, you would have had to have been watching baseball in 1956.

So if you were 8 years old then and watching Mel Parnell in his final season, you’re 66 now and probably have a distinct appreciation for how rare a lefty of Lester’s magnitude is in Red Sox history.


Oh, there have been some very good ones since — Bill Lee and Bruce Hurst among them. In a quest for context after Lester was traded to the A’s in July, the esteemed scribe Bob Ryan determined Lester was the fourth-best southpaw starter in Red Sox history.

Of the three ahead of him, Parnell was the kid, having thrown his last pitch in ’56. Lefty Grove, second on Bob’s list, was done at age 41 in 1941. And No. 1 was Babe Ruth, who pitched just five big-league games after 1919. Turns out he wasn’t a good-hitting pitcher, but a good-pitching hitter.

I’m not sure we knew it while it was happening, but it’s the truth. Lester is the best lefthanded Red Sox pitcher over a prolonged period that you — and probably your dad, and maybe even your granddad too — has ever seen.

7. The hell with Thomas Wolfe. In the figurative sense, Lester, like the rest of us mortals, of course cannot go home again. We can live in the moment and anticipate the future, but we can never truly revisit our fondest days past.

In the literal sense, he can’t go home again, either — he actually sold his place in Newton in November.

But by returning to the Red Sox, by returning to Fenway and the scene of so many successes, he could come as close to fulfilling an authentic return home as anyone can hope to achieve.

From someone who told you he was never coming back, I say this as genuinely as I can: Here’s hoping Jon Lester chooses the Red Sox, again.

Jump To Comments


This discussion has ended. Please join elsewhere on