In his first nine years in league, Roger Clemens amassed a 152-72 record while posting a minuscule 2.80 ERA with the Boston Red Sox. During that time, he won three Cy Young Awards and an MVP — a rarity for a pitcher. He was easily on his way to being one of the best pitchers in baseball history.
But between 1993 and 1996, Clemens was a shell of his former self. He would show up to spring training clearly out of shape, and it appeared he had lost it. Clemens posted an underwhelming 40-39 record with a 3.77 E.R.A. After the 1996 season, Red Sox General Manager Dan Duquette opted not to re-sign Clemens, then 33. Duquette famously remarked that he had wanted to keep Clemens in Boston during the "twilight of his career."
That didn't sit well with Clemens, who proceeded to sign with the Toronto Blue Jays and win back-to-back Cy Youngs. In Toronto, Clemens met personal trainer and steroid injecting enthusiast Brian McNamee. After two years in Canada, Clemens signed with the New York Yankees, where he won two World Series titles and a Cy Young.