The tragic derailment of Chris Sale's Red Sox career

In March 2019, the Red Sox gave ace pitcher Chris Sale a five-year, $145 million extension — at an average annual value of $29 million. At the time of the contract, it was the fifth largest AAV for a pitcher of all time. Fresh off of a World Series title, Red Sox fans thought they had their ace locked down for the next half-decade. If only they knew what was on the horizon.

In 2019, for the first time in his entire career, Sale was not himself. He compiled a 4.40 ERA — by far the worst of his career and a shock to Red Sox and baseball fans alike, who had watched him do nothing but dominate for the last two seasons. After dealing with lingering elbow problems, he was placed on the 10-day IL in August and later the 60-day IL in September with elbow inflammation. Then, in 2020, Red Sox fans got the news that they so greatly feared: he needed Tommy John Surgery. 

Sale underwent surgery in March of 2020, missed all of 2020, and most of 2021. But, with Tommy John in the rearview, Sale was hoping for a bounce-back 2022. Not so fast. After suffering a right rib stress fracture, he was placed on the 60-day IL before the season even began. Then, in just his second start back from the rib injury, he took a line drive to his throwing hand, fracturing his left pinky. As he recovered from his finger surgery, he broke his right wrist falling off a bike — as many times as I hear this one, it still shocks me — putting an end to his 2022 and leaving us in the current baseball season.

2023 marked the first Opening Day that Sale was healthy for since 2019. He started the season poorly, pitching to an 8.22 ERA across his first five starts. But in his next six starts, he rolled to a 2.25 ERA and tallied 41 strikeouts across 36 innings. Could it be? Could the vintage Chris Sale be back? Nope, not so fast. On June 1, he exited his start early due to left shoulder soreness. And on June 9, the Red Sox placed him on the 60-day IL with a stress reaction in his shoulder blade. You just can’t make it up.

Chris Sale just can't stay healthy

So what happened to one of baseball’s best pitchers? To the man with that wicked slider that made hitters look foolish? To the man who was the fastest to 2,000 strikeouts in baseball history? To the man who won a World Series? It’s simple: he has completely failed to stay healthy. Whether it was bad luck (a comebacker to the hand), his weak frame (weighing just 180 pounds), or flat-out poor decision-making (falling off a bike — yes, this falls under poor decision-making because he does not get the excuse of being an 8-year-old), Sale has been on the IL for some portion of six straight seasons. In total, he has spent considerably more time on the IL than not.

He has hurt basically every part of his arm — his shoulder, his elbow, his wrist, and one of his fingers. He received three surgeries in three years — Tommy John, finger, and wrist surgery. The sheer number of injuries that Sale has endured is just unprecedented.

As much as you feel for the guy, you start to realize just how disastrous his contract has been. Sale has started just 22 games since 2020. For context, since signing his massive contract with the Yanks in late 2019, Gerrit Cole has started 95 games — 73 more than Sale. And he’s got one year worth $27.5 million left on a contract that must go down as one of the worst in MLB history.

Oh, and don’t forget, he’s got a deferred contract worth five years, $50 million. That means a 50-year-old Sale will receive $10 million in the year 2039. Unfortunately, when "Chris Sale Day" comes around in the 2030s, it will be a day not of celebrating but a day of longing for what could have been.