Red Sox’s Decision to Lowball (and Trade) Jon Lester Looks Worse Every Day

A year ago tomorrow, Jon Lester continued to stake his claim as October’s resident ace, shutting down St. Louis for 7.2 scoreless innings in Game 1 of the World Series. His Cardinal counterpart, Adam Wainwright, sapped all suspense from the expected duel by allowing five runs in the first two innings of the Red Sox’ 8-1 victory.

Lester was just as steady and sensational in his next start five days later, recording the first 23 outs again while allowing four hits and a run in a 3-1 win. The duplicated masterpiece put the Red Sox on the brink of their first World Series title in six years (sounds way cooler than 86). They locked it up two days later. Lester probably would have been the Most Valuable Player had David Ortiz not hit, you know, .688.

I bring this up now for three reasons. 1) Man, that feels like longer ago than just a year. 2) Last October is always worth revisiting, no reason required. 3) The recent developments this October remind us of just how badly the Red Sox bollixed up Lester’s contract year.

They low-balled the free-agent-to-be in the spring, offering a reported four-year, $70 million deal when something in the 5/$100 mil range might have sealed the deal with the dependable, durable 30-year-old lefthander.

When he pitched through the spring and summer with the same dominance he demonstrated last October, the price, to paraphrase Mo Vaughn, went up every day.

Yet there was never any public urgency — or even apparent inclination — that they intended to pay Lester, a home-grown star pitcher who loved it here, anything resembling the going rate.

All we got were barely veiled hints that paying players over the age of 30 was a particularly foolish way for a franchise to allocate its resources.

The suspicion that Lester wasn’t long for Boston became reality on July 31. The Red Sox bid an awkward farewell and traded him at the deadline to Oakland, a franchise that actually would be playing meaningful games this fall.

While I have not for a fleeting second joined the hopeful segment of Red Sox fans that this is all a great ruse and Lester will re-sign here over the winter, I do understand the justification for the trade. They had made an informed determination of Lester’s value, and it didn’t jibe with the much greater salary the free-agent market will dictate.

So they did what was good for business, if not the ballclub, and made an interesting trade, acquiring flawed but fun power-hitting outfielder Yoenis Cespedes and a competitive-balance round draft choice. Given the scarcity of true sluggers these days, it was an intriguing move to acquire Cespedes rather than a small flock of prospects.

Three months later, though, you have to wonder whether the deal is about to backfire in a couple of different ways.

Cespedes, who had a knack for timely hits but just a .719 OPS in 55 games in Boston, has hired Jay Z’s Roc Nation sports agency as his representatives as he enters the final year of his contract. That is not the action of someone who is going to sign a market-value extension this offseason.

The Red Sox could trade him this winter — he’s productive and affordable for the ’15 season at $10.5 million. But where does that get you? Or what does that get you? More prospects for an organization that already has too much redundancy on its prospect depth charts? It’s hard to figure they’ll receive any prospects worthy of much hype given the single year left on Cespedes’s deal, which does not have draft-pick compensation attached.

And how exactly to they plan to replace Lester at the front of the rotation? Perhaps they could trade some of those prospects for Philadelphia’s Cole Hamels, a reasonable facsimile of Lester who pitches at the rate (four years, $90 million) that the Red Sox presumably would have been willing to pay the original.

Consider yourself forewarned: If they do make a Hamels deal, the prospects they will part with will not be the ones you and I consider expendable. We’re going to see a promising kid or two depart whom we were looking forward to watching in Fenway soon. This is not going to be Will Middlebrooks, Anthony Ranaudo and Allen Webster for Hamels, you know?

(Actually … any interest in that, Ruben Jr.? You never know with that guy.)

And what do we make of James Shields now, after one more lousy postseason performance in what is now a 10-start sample size? He has a 5.74 ERA in 53.1 innings in the playoffs. He hasn’t pitched beyond the sixth inning in a postseason start since 2008, when he went 7.1 innings in a 2-0 loss to Daisuke Matsuzaka and the Red Sox in the Game 2 of the ALCS. His nickname — Big Game James — has become a punchline without much of a setup.

The Red Sox are said to covet him, and that is understandable to a degree. He is a regular-season workhorse — he had a 3.21 ERA in 227 innings for the Royals this year — and he’s said to be a positive and willing influence on young pitchers. He’s a free-agent, just like Lester, but the presumption is because he’ll begin next season at age 33 he won’t command a long-term deal.

The Red Sox may be willing to pay him a high average annual value on a shorter deal, but still, such an approach comes with a lingering question: Would you rather have the older Shields on a lucrative three-year deal, or soon-to-be-31-year-old Jon Lester for the five that might have been doable in Fort Myers?

I know my answer. Especially at this time of year, and yes, even with the acknowledgment that Shields’s Royals beat Lester’s A’s in the wild-card game.

The pitchers who fit the criteria for what they need and what they’re looking at their preferred length of term and price are few and far between.

You say you want an accomplished pitcher not too far beyond age 30 with recent postseason success who won’t command more than a three-year deal?

That’s not James Shields. That’s not Jon Lester, either.

It’s Jake Peavy,

And I can’t believe he’s starting Game 2 of the World Series, either.