What if Red Sox never let Roger Clemens leave in free agency?

Retaining Roger Clemens when he hit free agency would have created a ripple effect altering the direction of the franchise – for better and for worse.

Roger Clemens spent the first 13 seasons of his major league career wearing a Boston Red Sox uniform. Over that span, he piled up a handful of All-Star appearances, three Cy Young awards, an MVP, and tied the franchise record with 192 wins. Those accolades are enough to fill an impressive lifetime resume but for Clemens, it was only the first act of his career.

The Rocket was the most coveted pitcher on the market when he hit free agency after the 1996 season. He was coming off a solid year in which he posted a 3.63 ERA and led the league in strikeouts but Clemens wasn’t quite as dominant as he had been at his peak and posted sub-par seasons with an ERA north of 4.00 in two of the previous three years.

Dan Duquette’s infamous quote about Clemens being in the “twilight” of his career may have been taken out of context but it did seem as if the star pitcher was fading at the time. That doesn’t mean the Red Sox were ready to push him out of town though. They did offer Clemens a lucrative contract in an effort to keep him in Boston, it just wasn’t enough.

The Toronto Blue Jays lured Clemens north of the border with a four-year deal worth up to $40 million (including incentives and an option on the fourth year). The contract made Clemens the richest pitcher in baseball history at the time.

Some bad blood developed between the organization and their ace at the end of Clemens’ tenure with the team. Clemens felt disrespected by Duquette implying his career was nearing the end of the line. Red Sox fans turned on the “Texas Con Man” when he left and it took years to mend those wounds.

Clemens has since been welcomed back to Fenway Park and he was inducted into the Red Sox Hall of Fame but how would history have unfolded if he never left to begin with?