Boston Red Sox: Reassessing the disastrous Chris Sale deal

The Boston Red Sox should have known better when they re-signed Chris Sale. They paid a high price, lost a key outfielder and got a damaged pitcher.

When the Boston Red Sox re-upped Chris Sale for five seasons at $150 million, the consequences of that action should have been immediately obvious. But the Sox, at the time under the direction of President of Baseball Ops Dave Dombrowski, signed the papers anyway.

They are now reaping those obvious fruits, almost all of them negative.

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When Sale signed that deal, he and the team were coming off a World Championship 2018 season in which he had been an integral part of the rotation. That included three post-season appearances, one of them in the World Series, along with a relief appearance in the clincher. Sale threw the Series’ final pitch.

With free agency looming at the end of 2019, the Red Sox exercised what they viewed as discretion, taking Sale off the market, even at the expense of paying his price.

The deal has hurt the Red Sox in many ways that should have been obvious at the time. That the consequences weren’t obvious to the Red Sox should serve as a cautionary tale to any team considering throwing huge money after an arm, even one of its own.

The first and most obvious problem was what it did to the core of Boston’s lineup. Given the team’s payroll situation, committing that much money to Chris Sale effectively forced the Red Sox to come to terms with the fact they would not be able to keep all of their young and highly-priced talent very much longer.

At the time, that talent horde included Mookie Betts, Jack Bradley Jr., Xander Bogaerts, Andrew Benintendi and Rafael Devers, all productive parts of the World Series winners, all in their 20s and all on the fringes of becoming non-controllable.

Sure enough, the Sale signing drove Boston’s 2019 payroll north of $236 million, and within a year forced the salary dump trade of Betts and David Price to the Dodgers.

It also rendered the Red Sox incapable of competing in the 2020 free-agent market for any infusion of talent…although they did lock up Bogaerts for six seasons at $120 million.

Finally, it presumed something not in evidence at the time, namely Sale’s ongoing health. He had missed time in 2018 for shoulder inflammation, a warning sign among pitchers if ever there was one. In 2019, elbow problems sidelined Sale for the season’s final six weeks.

Those problems have continued into this spring. A flexor strain sent him to the doctor for an MRI this week, and although the Red Sox say they don’t think Tommy John surgery will be required Sale himself has not ruled that possibility out.

In short, the impact of the Sale contract on the 2020 Red Sox may well end up being the loss of Betts and Price offset by the gain of … nothing through 2020 or longer.

There are certain things teams should always be hesitant to do, and one of them is signing plus-30-year old pitchers to long-term costly deals. That’s true even when local fan pressure demands such a move. Sale, for the record, turns 31 at month’s end.

That warning is doubled if the pitcher has had recent arm problems, and it’s quadrupled if the team is already carrying a host of heavy contracts that would jeopardize its future payroll flexibility.

In signing Chris Sale, the Boston Red Sox ignored all of those warnings, and they appear certain to pay for it.

As for Dombrowski, the guy who actually did the deed, he’s already paid for it. The Red Sox fired him last summer.