Chris Sale is the latest example of the Red Sox compounding their mistakes

The Sox erred with Jon Lester, and they erred by giving Sale a huge extension

At a crossroads, the Red Sox looked back to the road not taken with Jon Lester to guide their path forward with Chris Sale (above).
At a crossroads, the Red Sox looked back to the road not taken with Jon Lester to guide their path forward with Chris Sale (above).Barry Chin/Globe Staff

The Red Sox made a mistake lavishing Chris Sale last year with a five-year, $145 million extension that kicks in this year. That’s obvious in 2020 hardball hindsight. However, the pathology of that mistake isn’t so obvious. It was a blunder created as much by absolution as evaluation.

Instead of carving up hitters in 2020, Sale went under the knife on Monday, his 31st birthday, undergoing Tommy John surgery to repair his pricey and faulty left elbow. The procedure was performed by Dr. Neal ElAttrache, the same doctor who repaired Tom Brady’s torn ACL in 2008. Sale is out of commission this season — assuming there is one — and likely until June of 2021.


The problem with the Sale signing was that it was a mistake born of trying to rectify an earlier error with a previous Boston lefthanded ace, Jon Lester, the one who never should've gotten away. Lester was the driving force behind Sale's extension, even though the two pitchers are about as similar in durability as a chiffon blouse and a wool blazer. Sale is a better pitcher, but Lester is a better investment.

Jon Lester, with the Cubs since 2015, is the ace lefthander the Red Sox should have signed to a contract extension.
Jon Lester, with the Cubs since 2015, is the ace lefthander the Red Sox should have signed to a contract extension.Jim Davis/Globe Staff

Lester was and is a workhorse with the hindquarters of an NFL running back. He's built to last. Sale is an electric, but spindly ace, who has the build of a match stick and never makes it to October at full strength.

The Sox plowed right through the stop signs of fragility that Sale's body put up in a desperate attempt to not make the same mistake twice. Instead, in their zeal, they made a brand new one that's arguably even worse.

The fingerprints of the failed signing of Lester, low-balled by the team during spring training in 2014 and eventually traded to the Oakland A’s when the season unraveled, are all over the predicament the Sox find themselves in now with their idled ace. It was last year during the annual ownership spring training address that Red Sox principal owner John Henry (you know what else he owns) delved into the past when discussing Sale’s situation, admitting that the Sox erred in being overly cautious — to put it gently — in their contract approach to Lester.


"I think we blew the Jon Lester — we blew the signing in spring training,” Henry said. "And for reasons that are pretty apparent now, which I won’t go into, but they’re apparent. But it wasn’t … you can see what’s gone on in free agency. The price of WAR [wins above replacement] has gone up [so] radically that it’s difficult, whether it’s a pitcher or a position player, entering into a really long-term contract with high dollars. And we haven’t had a great track record.”

Like Sale last year, Lester was a lefty ace coming off a World Series-winning season entering his walk year. At a crossroads, faced with a difficult decision, the Sox looked back to the road not taken with Lester to guide their path forward with Sale, a crucial error.

In 2014, the Sox decided to play hardball with the 30-year-old Lester, fueled in part by Henry’s ideological stance at the time that teams shouldn’t trust anyone over 30 when it came to lucrative long-term contracts. That rallying cry was famously articulated by Henry in a 2014 story in Bloomberg Businessweek in which he cited a study presented at the MIT Sloan Sports Analytics Conference.


“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.”

Words are like rope. They can tie you in knots.

This would prove as the (mis-)guiding principle in the Sox’ failed negotiations with Lester. It was what ultimately led to the homegrown lefty landing in Chicago with former Sox GM Theo Epstein on a six-year, $155 million contract, even after the Sox re-entered the fray during free agency. That contract is in its final non-option year.

Chris Sale will be out for all of 2020.
Chris Sale will be out for all of 2020.Barry Chin/Globe Staff

While Lester hasn’t been elite on a Sale or Max Scherzer level, he has been reliable, winning double-digit games and making 30 starts every season of the deal. From 2015 to 2019, the Cubs are 101-58 (.635) in Lester’s starts. Plus, you can’t put a price on busting a 108-year World Series drought.

Chicago won the World Series in 2016, and Lester was co-MVP of the National League Championship Series that year. The lymphoma survivor is 74-41 with a 3.54 ERA in the regular season with the Cubs and 3-3 with a 2.44 ERA in the postseason.

Everyone in baseball is looking for universal truths, fool-proof approaches derived from analytics. Yet, there are no absolutes in player projection.


Foolhardily swearing off major commitments to pitchers over 30 and then committing major money to the wrong one are both serious misjudgments. The Sox fixed their approach, but then applied the revision to the wrong guy.

Removing the scars of the failed Lester negotiations from the equation, locking up Sale was a risky proposition. His stuff is undeniably brilliant, but what's also undeniable is that he never seems to make it to the finish line pitching at his peak.

He faded down the stretch in 2017 and then got lit up in the playoffs, posting an 8.38 ERA. (Some of that could have had to do with the Houston Astros sign-stealing.) Shoulder issues shut him down in 2018 while he was sailing to the Cy Young Award, limiting Sale to five regular-season starts after July 27 and a complementary role as the Sox won the World Series. After he got his extension last season, elbow trouble truncated a perplexing campaign (6-11, 4.40 ERA despite a stellar 13.3 strikeouts per 9) in mid-August and led to him receiving PRP (platelet-rich plasma) injections to try to ward off reconstructive elbow surgery.

You feel bad for Sale because he fervently desires to hold up his end of the bargain, but his body won’t let him. He’s dynamic, but his durability has declined as his odometer has risen. His win totals, innings pitched, and starts have decreased each season in Boston.

Now, the Sox are resigned to 2½ seasons with Sale as more ACE bandage than ace.


What the Sox seem to struggle with sometimes is understanding the distinctions and nuances of each situation. The reason that Triple A outfielder emeritus Rusney Castillo was inked in 2014 to the seven-year, $72.5 million that the Sox are dodging like a bill collector by exiling him to the minors for luxury tax purposes is simple. It’s because Boston was outbid by the Chicago White Sox for fellow Cuban free agent Jose Abreu the previous year.

One mistake begat another.

Chris Sale faces an uncertain future.
Chris Sale faces an uncertain future.Jim Davis/Globe Staff

This is a pattern with the Sox, and it has extended from Epstein to Ben Cherington to Dave Dombrowski, who took the rap for the Sale signing. The Sox get burned in free agency by a Carl Crawford. Then they retrench too far in the other direction for a team with their considerable resources and lose a Lester. Then the pendulum swings back and they end up with busts such as Pablo Sandoval and Hanley Ramirez. On it goes.

We are all influenced by our choices, particularly the ones we regret. But the Sox have to break the cycle of double-back then double-down decision-making.

It compounds the original sin with a new one.

Christopher L. Gasper is a Globe columnist. He can be reached at christopher.gasper@globe.com. Follow him on Twitter @cgasper.