It’s Tough to See Jon Lester Go, but Acquiring Yoenis Cespedes is a Fascinating Move

I believe I’m among a majority around here in that I wanted the Red Sox to pay the steep going rate for a pitcher of Jon Lester’s accomplishment and ability, even with the over-documented risks of committing multiple years and millions upon millions of dollars to a player over 30.

I wanted him to be Red Sox lifer, to be their Andy Pettitte (minus the Houston detour), to win third championship and maybe more for this team. I imagine you did, too. And I’m convinced he did, too.

Instead, he’ll be pitching for his third title — and second in a row — in the green and gold of the Oakland A’s. The Red Sox sent him west, along with Jonny Gomes, for dynamic, flawed outfielder Yoenis Cespedes and a competitive balance draft pick this morning. It’s a fascinating deal, invigorating and disappointing all at once.


At the least, it will be nice to see a couple of important members of last year’s champs play meaningful games this October. It’s sure not happening at Fenway this fall.

Some reasons for desiring to retain Lester were sentimental, sure — he loved it here, grew up here, won here, survived bleepin’ cancer here.

But most reasons had to do with baseball matters. He’s a remarkably durable top-of-the-rotation lefthander who delivers time and again in big moments and continues to hone his skills as he ages.

Pitchers like Lester aren’t easy to find in any market, and that’s why his next contract will pay him $100 million beyond what the Red Sox offered him in spring training.

He’s gone, and there’s zero chance he returns once six or seven teams are in on the bidding. He’s probably not coming back to Boston like Pettitte returned to New York, at least not anytime soon. Hell, he’ll probably end up in New York.

That necessary appreciation for an admirable now-former Red Sox star out of the way … holy smokes, what a fascinating trade.

I figured this morning, as we waited for deadline day to play out, that Oakland or Pittsburgh would be the two most likely suitors for Lester. The Pirates had the prospects and the desperation, while Billy Beane is loading up the A’s with a rotation that rivals the Zito-Hudson-Mulder trio that may or may not have been mentioned more than once in “Moneyball.”


When news first broke around 10 a.m., I suspect we all had the same reaction. “They traded him to Oakland … WAIT, WHAT? FOR CESPEDES?!”

It’s a thrilling old-school baseball trade that, at least on the Boston end, wasn’t made entirely for baseball reasons. But the Red Sox, currently as dull as any team they’ve had since the Butch Hobson years, just ratcheted up their entertainment value. That they made the deal six hours before the deadline has to be taken as confirmation of how much Ben Cherington liked the return.

He should like it, and those among us who were resigned to Lester being traded should like it too.

Cespedes is as fun to watch as his name is to say. A three-year veteran at 28 after defecting from Cuba, is a one-man force of nature, albeit one who still has some recklessness in his game.

His top statistical comp, Bryce Harper, is also an appropriate stylistic comp. Cespedes is seven years older than Harper, and he should not be as raw. But it he is.

For the most part, his sporadic blunders are tolerable because he masks them with an enticing array of raw skills.

He’s a blast to watch defensively, and the Red Sox may not require a third outfielder with Cespedes and Jackie Bradley Jr. covering all of that outfield mileage. Perhaps Shane Victorino can move to rover or something.

He’s a two-time Home Run Derby winner who approaches his at-bats like … well, like he’s in a Home Run Derby. He’ll hit some bombs that buzz over the heads of those situated in the Monster Seats, but his on-base percentage (.303 this season, .318 career) doesn’t exactly jibe with the Red Sox’ keep-the-line-moving philosophy.


And I think you have to be curious how long Cespedes will be a member of the Red Sox. He’s signed through next season, but he does strike you as a potential piece to a bigger trade. I think you know where I’m going with this. Don’t you wonder what the Marlins think of him?

For now, in a season that is already lost, at least Cespedes offers a reason to tune in. And while the Red Sox prepare to play out the string, the deal also gives us another rooting interest.

Don’t know about you, but I know which team I’m rooting for this postseason. They wear green and gold, feature a lot of familiar faces, and just picked up one hell of a lefthanded pitcher today.

What a strange baseball universe this has become. Jon Lester, Billy Beane and the A’s are going for it, while it’s now the Red Sox who are putting the money before the ball.

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