Adam Kaufman

Jon Lester Would Be Foolish to Re-Sign with Red Sox Before Testing Free Agency

Jon Lester 10.jpg

Entering the season, I was as optimistic as anyone about Boston’s chances of repeating as World Series champs or, at the very least, floating atop the deficient American League East.

As we approach mid-July and baseball’s All-Star Break, those hopes have clearly evaporated, even for those clinging to the increasingly irrational belief that a wild card playoff spot is within reach.

At this point, most discussions have turned to not whether the Red Sox should be sellers, but whom they should sell off. We’ll save that list for another day. For now, the focus is on free-agent-to-be Jon Lester and whether he’ll still call Fenway home on Opening Day in 2015.

Like most of you, I’d imagine, I certainly hope so. The Red Sox would be foolish to deal their ace unless they’re convinced he’ll depart this winter. If there’s positively no hope at signing the 30-year-old southpaw then, sure, it makes sense to get more than a measly draft pick in return.

But, the flipside is obviously that the Sox have some control – or considerable influence – over the situation. For the right money, their ace isn’t going anywhere. Lester has said numerous times he has no desire to leave the only professional organization he’s ever known.

However, it would simply be bad business if Lester didn’t explore his options.

The recently named three-time All-Star is enjoying the best season of his nine-year career. Don’t be deceived by his run support-lacking 9-7 record. Durable as ever, Lester has pitched 122 innings over 18 starts and produced personal-best totals with a 2.73 ERA (previous low was 3.21 in 2008), a 1.15 WHIP (it was 1.20 in 2010), 2.1 walks per nine innings (he’s limited the free bases to 2.8 per nine frames on three occasions), and a ridiculous 4.21 strikeout-to-walk ratio (it was 3.52 in 2009).

Maybe Lester is stepping up at just the right time, but that track record goes beyond this season.

Dating back to his first start after the 2013 All-Star Break – which admittedly followed a trying 18 months – the lefty is 20-10 over 244 1/3 innings spanning 36 starts, aided by a 2.50 ERA. That includes his admirable postseason presentation.

Since June 12, Lester is 3-0 with a 0.96 ERA and he hasn’t allowed an earned run in his last two starts (totaling 16 innings). Boston has won seven of his last eight outings since May 27. Not bad for a team 12 games below .500.

Riding a run like that and entering a class of free agents that includes Max Scherzer – who will likely set the market – and less accomplished starters James Shields and Justin Masterson, Lester is in a great position of strength at the negotiating table so long as he doesn’t get hurt or implode in the next few months.

Lester has led us to believe that no new deal is on the horizon after he said Saturday, “both sides right now are happy with not talking right now.” Unless the Red Sox overwhelm him with an offer over the break – rather than insult him with something like a four-year, $70 million pact, as the club did back in the spring – there might not be anything to discuss.

I’ve long believed Lester’s supposed willingness to take a hometown discount would be defined by years and overall dollars rather than average annual value because of his desire to be paid what’s commensurate with his market value. In turn, five years and around $110-120 million made perfect sense during spring training. Even while Scherzer was rejecting a six-year, $144 million offer from the Tigers, it felt like the more modest terms would get the job done and end the conversation. Instead, the Red Sox went with the lowball approach and Lester launched into his prove-it campaign. For him, it’s worked out beautifully.

Now, with his price tag rising virtually every start, he should finish the job by waiting out the season, testing the market, and seeing if the Yankees (who may lose CC Sabathia for good), Tigers (if Scherzer signs elsewhere), one of the Los Angeles teams, or another financially flexible squad is prepared to give him the six years and $150 million the market will likely dictate he deserves. He owes it to himself; he’ll never have another opportunity like this for as long as he plays.

Dripping in money and committed only to Dustin Pedroia in 2016, the Red Sox must make their best pitch sooner rather than later to give Lester something to strongly consider and hopefully prevent that previous scenario. From there, he can decide how passionately he wants to remain on Yawkey Way. In a perfect world, perhaps for both sides, he’ll leave money on the table, stay put, and no one will have to rip that jersey off his back.

For Boston, there is nothing but question marks when thinking beyond Lester. If he leaves, the Sox will still need an ace at the top of their staff in 2015, when contending hopes will return as dependably as April showers and May flowers.

There’s no telling if it will be John Lackey, who has reportedly threatened retirement over pitching for $500,000 next season. Clay Buchholz is as unpredictable start-to-start as he is season-to-season. Brandon Workman and Rubby De La Rosa aren’t ready for that responsibility. And a free agent – who may very well command dollars approaching Lester’s asking price – wouldn’t necessarily be able to cut it in the AL East, deal with the rigors of the city’s fan and media influenced pressure and scrutiny, or in the postseason.

Checkmarks across the board for Lester, thus giving him even more power.

Ultimately, the Red Sox’ ace holds the vast majority of the cards here and ownership has most certainly lost its bargaining power. What once may have taken $20 million annually may now require $25 mil. When five years may have previously been enough, vesting options for additional service time might now be necessarily.

Credit Lester for pitching with great poise, confidence, and without distraction this season, and never letting his mind get the best of his mouth in the face of rumors, rumblings, and media dissection. Ideally, the Sox will clean up their mess before it’s too late, but it’d be tough to blame Lester for making them sweat it out a little during his free agent freedom.

Follow me on Twitter at @AdamMKaufman

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