What if Red Sox never let Roger Clemens leave in free agency?
By Sean Penney
Post-Boston career
Clemens immediately silenced his doubters with consecutive Cy Young campaigns with the Blue Jays. He went 41-13 with a 2.33 ERA and 10.2 K/9 in two seasons in Toronto.
His dominance on the mound wasn’t enough to lift the Jays to the postseason so they traded him prior to the 1999 season to the reigning champion New York Yankees. The rich got richer and adding Clemens to the top of their rotation helped the Yankees capture two more championships in his first two years in the Bronx.
Clemens would go on to earn two more Cy Young awards, giving him a major league-record seven, over the remainder of his career split between the Yankees and his hometown Houston Astros.
His numbers were already worthy of the Hall of Fame when he left Boston but by the end of his career, Clemens had arguably piled up enough accolades to be considered the best pitcher in MLB history. Unfortunately, his entrance into Cooperstown remains blocked by a legacy tainted by performance enhancing drugs.
While it was never technically proven, there’s enough damning evidence to convince the court of opinion that Clemens was a PED user. It’s fairly easy to pinpoint when he started using, considering the drastic turnaround from fading star in his final years in Boston to the best in baseball once he arrived in Toronto.
Was it a burning desire to prove the Red Sox wrong that pushed him to start cheating? Perhaps he wouldn’t have been tempted to turn to the dark side if his relationship with the Red Sox hadn’t been spoiled. If Duquette had stayed on his good side and locked up his ace with an extension, Clemens may have finished out the final few years of his career in Boston.
He wouldn’t have lasted until he was 44 years old and almost certainly wouldn’t have piled up four more Cy Young awards without a boost from PEDs. However, he probably would have had a few solid years left in the tank, enough to keep the Red Sox in contention while adding to a legacy that surely would have put him in the Hall of Fame by now.