The Red Sox were as busy as any team during last spring’s extension flurry, inking a pair of star players to long-term deals that kept them out of the 2019-2020 free agent market.  One of the extensions was a six-year deal with Xander Bogaerts worth $120MM in guaranteed money, a contract that now looks like a pretty sound investment given how Bogaerts followed up a strong 2018 season with an even better 2019 campaign.

The other extension is already off to a rough start.  Chris Sale signed a five-year, $145MM pact covering the 2020-24 seasons, with a club/vesting option for the 2025 campaign worth at least $20MM.  After vastly outperforming his early-career extension with the White Sox (which ended up as a seven-year, $59MM deal once both option years were exercised), Sale now had a new deal that better reflected his status as one of the better pitchers over the last decade.

Exactly one year after that extension was signed, however, the deal looms as a significant misfire for the Red Sox on a couple of different levels.  The club announced on Thursday that Sale would be undergoing Tommy John surgery, which will keep him out of action for whatever becomes of the 2020 season and, in all likelihood, around half of the 2021 season.  The surgery comes on the heels of Sale being shut down last August due to elbow inflamation, and while a platelet-rich plasma injection and some months of rest looked to have the left-hander back on track earlier this winter, Sale was shut down again earlier this month after suffering a flexor strain.

In the short term, this means Boston loses its best pitcher for 2020.  It is a major blow to a rotation that was only okay in 2019, and already had lost David Price after the Sox traded the veteran southpaw and Mookie Betts to the Dodgers in February.  While Sale could conceivably get back to something close to his old form post-surgery and still pitch well over the rest of his contract, the Betts/Price trade plays a critical role in evaluating the big-picture impact of Sale’s extension.