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

Consequences

Re-signing Clemens could have had negative consequences for the Red Sox. Let’s avoid the obvious fear of an expensive pitcher declining rapidly if he weren’t illegally enhancing his performance. We’ll never know how Clemens would have aged without PEDs.

Instead, let’s explore another angle of the fallout of keeping Clemens. If Boston shelled out enough to satisfy Clemens, would they have still made the trade for Pedro?

The Red Sox inked Martinez to a 6-year, $75 million extension after he arrived from Montreal. It was the largest contract ever given to a pitcher at the time, with an average annual value easily topping the approximately $8.5 million Clemens was making.

Boston was eighth in the majors with a payroll of about $51 million in Pedro’s first year with the franchise. Having Clemens on the payroll at the same time would have pushed them up to around $60 million, right behind the Yankees for the third-highest in baseball. While that doesn’t seem like a steep total by today’s standards, it would have been the highest payroll in franchise history at the time. Boston hadn’t been among three highest payrolls in the majors since 1991 and they wouldn’t venture into top-three territory again until 2001.

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If Clemens stayed in Boston then the Red Sox wouldn’t have felt as pressured to find a new top of the rotation starter and it’s unlikely they would have been able to afford both. We could have been robbed of seeing Pedro at his best.

Boston doesn’t win the 2004 World Series without Pedro. Clemens probably would have been retired by that point without PEDs extending his career. If he somehow was still hanging on into his 40s without steroids to fuel him, Clemens still may very well have bolted for Houston that year.

If Clemens was gone and Pedro never came, do the Red Sox consider their chances of contention strong enough to pull off the Curt Schilling trade? They definitely aren’t reversing the curse without Schilling and his bloody sock, further extending the franchise’s title drought. Schilling also played a key role in the 2007 title so if the Red Sox never acquired him from Arizona then that’s a second title potentially lost.