Will Lessons Learned From Jon Lester Affect Red Sox’s Chris Sale Contract Talks?

John Henry won’t say he’s had a shift in his philosophical beliefs, but his spending habits may ultimately suggest otherwise.

The Boston Red Sox owner was rather candid Monday when he admitted the club “blew” contract negotiations with Jon Lester back in spring training of 2014. At the time, Henry and the Red Sox had reservations about signing aging pitchers to long-term contract extensions, and many believe the club lowballed Lester with a reported offer of four years and $70 million prior to the lefty’s walk year.

The initial offer set the tone for unsuccessful negotiations, and the Red Sox ultimately traded Lester at the 2014 deadline. A few months later, Lester signed a six-year, $155 million contract with the Chicago Cubs that has been beneficial to both sides thus far.

“I think we blew the Jon Lester (situation),” Henry told reporters Monday at a press conference in Fort Myers, Fla. “For reasons that are pretty apparent now … it wasn’t, you can see what’s gone on in free agency that the price of WAR has gone up so radically where it’s difficult that a pitcher or a position player to enter into really long-term contracts at high dollars. We’ve done better I think with pitchers than we have with hitters in really long-term contracts.”

Henry’s change in thinking came a year later when the Red Sox signed David Price, then 30, to a record-setting seven-year, $217 million contract. Now, with Chris Sale entering the final season of his contract, the Red Sox have another decision to make as it pertains to an “aging” pitcher. Sale will turn 30 next month, but the club has discussed a new contract with the seven-time All-Star.

“I think Chris falls out of the norm because he’s not just a great pitcher but a great part of the team as we saw in the World Series,” Henry said. “He had quite an impact just being on the bench in the World Series. He’s a special player. We would love to be able to sign him, I think he would like to as well, but there are realities of the marketplace — budgets, this is his opportunity to be a free agent potentially, which we’d like to avoid, and I think he would as well, so something could happen.”

Of course, it’s unlikely the Red Sox go crazy bidding against themselves for Sale, too. The left-hander dealt with shoulder issues last seasons — an ailment downplayed Monday by Henry — and Boston is at a point where it’s going to have to start paying players set to enter free agency.

But at his best, Sale — like Lester — is one of the best pitchers in baseball and the cornerstone of a championship pitching staff. We’ll now see how much Henry’s viewpoints have changed and what kind of lessons they learned from Lester.