Christopher L. Gasper

Red Sox should do Jon Lester deal now

The state of the contract negotiations between the Red Sox and ace lefthander Jon Lester can be summed up best by the sage words of one Vincent Lamar Wilfork: “They know the longer it takes the more it costs.”

The Patriots nose tackle was talking about his own contract situation when he uttered those resonant words to me back in 2009, but they fit the Red Sox-Lester dance. The meter is running on Lester, and he’s the one in the driver’s seat. The Sox don’t know his asking price, but they do know it goes up by the day.

The more risk a player assumes by playing out a contract the less likely he is to let warm and fuzzy feelings for his employer get in the way of cold, hard cash. Lester has assumed the risk of having a healthy, productive season entering free agency, and now he’s in position to reap the rewards.


That’s why the Sox should make their best offer to Lester now. The days of a discount are over. The sturdy lefty throws a cutter, but he’s not going to do a cut-rate contract, along the lines of the four-year, $70 million offer the Sox sent his way in spring training. Re-signing Lester is going to require the Sox going well outside of their contract comfort zone, an artificial barrier they’ve erected that remains an impediment to a deal, along with Lester’s curious reluctance to re-engage in serious talks.

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The folks at 4 Yawkey Way have to decide what they value more — the player or their newfound monetary restraint? Only an eye-opening offer is going to get Lester back to the bargaining table in-season.

We’ve all heard of teams making playoff pushes. Lester is making a pay-day push. He is 4-0 with an 0.85 earned run average in his last seven starts. He is the Joe Flacco of free agent pitchers, a border-line elite player having an elite season at the most opportune time.

Lester entered Monday’s action fourth in the majors in fielding independent pitching (FIP), which for those who believe in advanced metrics is a more accurate assessment of a pitcher’s effectiveness than ERA. Lester’s FIP is 2.59, trailing only Clayton Kershaw, Felix Hernandez, and Adam Wainwright. Lester ranked second in WAR (wins above replacement) among major league pitchers at 4.5, trailing only Hernandez.

Sacrificing coveted prospects for 30-year-old Philadelphia Phillies ace Cole Hamels or signing Kansas City righthander James Shields, who entered Monday tied for the MLB lead in hits allowed, don’t represent better baseball bargains.


It’s obvious that being burned by bad long-term deals for Carl Crawford, Adrian Gonzalez, and Josh Beckett has scarred the Sox from commitment like a bad breakup.

They might be bigger commitment-phobes now than Rory McIlroy. Those deals, which the team holds up a wooden cross and a garlic clove at the mere mention of, have made them leery of spending the type of big bucks it will take to retain Lester.

Yes, the team signed Dustin Pedroia to an eight-year deal last season, but it was for a team-friendly average of $13.75 million per year.

Swearing off $20-million-plus per-year, long-term deals completely is just as bad as muttering profanities later about profligate spending. They’re different sides of the same coin.

It’s great to have guiding principles and core philosophies, but they can’t be inflexible. There are no absolutes in life or in business.


It’s also bad business for the Red Sox to abstain completely from top-of-the-market contracts because it negates one of the benefits of being the Boston Red Sox. The Sox are one of the few teams in major league baseball, along with the Yankees and Los Angeles Dodgers, that can afford to spend their way out of mistakes.

Sometimes, the Sox seem bent on building their team like they’re the Royals or the Oakland A’s. But it makes zero sense to cede one of their biggest competitive advantages, deep pockets.

Remember Edgar Renteria? The Sox paid $8 million to trade him in 2005 after he disappointed in the first year of a four-year, $40-million contract. Renteria wasn’t the only sunken-cost shortstop. The Sox signed Julio Lugo to a four-year, $36-million deal in 2006. They traded him to the Cardinals in 2009 and paid the remaining $13 million on his contract.

None of their failed free agent signings has been crippling for the Sox. If Lester, who will turn 31 in January, were to fall off performance-wise on the back end of a, say, six-year, $147 million deal, that wouldn’t be crippling either.

Part of the harsh reality of free agency is having to pay a player over five or six years if you want him for three or four years of prime production.

Lester has been underpaid based on performance for the last six years. He signed a five-year, $30 million extension, with a $13 million option for 2014, in 2009. If he is overpaid for the final three years of his next contract, that’s just part of baseball’s salary circle of life.

Much was made of the comments of Red Sox principal owner John Henry (also the owner of the Boston Globe) in Bloomberg Businessweek in April, citing a study that said cost-effective young players were becoming the most valuable commodity in baseball.

“To me, the most important thing this study shows is that virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30,” Henry told the magazine. “Yet teams continue to extravagantly overpay for players above the age of 30.”

In that same article, the author, Joshua Green, wrote: “What sets the Sox apart from the A’s is that they can afford to make such mistakes. They’re playing moneyball on a $155 million budget.”

There is no need to level the playing field or take Lester off it for the sake of philosophy.

Philosophies don’t win games. Players do.

Christopher L. Gasper is a Globe columnist and the host of Boston Sports Live. He can be reached at Follow him on Twitter @cgasper.