You mean the season with the lowest FIP by an American League starting pitcher in the 21st century? I thought it was alright too.
At that point (March 2019), it looked like Sale would have entered the same FA market as Gerrit Cole with better marks (but a year and a half older). He might not have gotten Cole’s 9/$324 contract, but it would surely have been much higher than 5/$145. It sucks that it hasn’t worked out but it made sense at the time.
- He had another year to go on his existing contract. There was zero need for the extension at that point in time.
- His injuries were up and his IP were down. He also struggled badly in the 2017 postseason and was just...meh in 2018.
- He had faded towards the end of both 2017 and 2018. He is also built like Shawn Bradley and thus breaks down constantly.
- The deal gave the Sox a terrible year from Sale in 2019, absolutely nothing in 2020, and 40 innings in 2021.
- (and you knew this was coming) It solidly put them over the luxury tax line at a time the FO knew Betts' contract was up. Given the choice of keeping the players, the astute GM keeps Betts every single time.
It was a highly questionable deal the moment it was signed, and it has lived up to every doubters' worst fears since then. It's the worst contract the Sox have given out since...Clement? I dunno. It's a horrible extension. He has never for one moment been worth the money. It was by far DD's most damaging action when he was in charge of the club. If only he had been fired before making that deal.
More urgently: he's hurt. Again. Costing the Sox a huge chunk of time without him. He's also going to be unable to play in any games in Toronto (and perhaps New York) because of his choices. At this point he's a expensive liability on the team.