Story byTom CarrollMon, December 8, 2025 at 5:20 AM UTC·3 min readMake no mistake about it, Red Sox fans have an extremely complicated relationship with retired starting pitcher Roger Clemens. Most members of a certain age in Red Sox Nation absolutely despise him. Not only did he leave Boston for a division rival in Toronto after the 1996 season, he then went on to become the ace of the Yankees’ staff on the tail end of their 1990s dynasty teams, winning two World Series in pinstripes in 1999 and 2000. AdvertisementAdvertisementAdvertisementAs Clemens’ talents declined into the 90s, he immediately became the best pitcher in the American League during his two seasons in Toronto, winning the AL Pitching Triple Crown in both 1997 and 1998. That led to consecutive Cy Young Awards before two more later in his career - one with the Yankees in 2001 and one with the Astros in 2004. There’s all sorts of reporting to suggest that Clemens’ second-half rebirth as a pitcher was due to chemical enhancements thanks to the use of PEDs and steroids. And while the Red Sox Hall of Famer has never publicly admitted to any wrongdoing in that regard, the court of public opinion has made up their mind.“Not only is he a cheater, but he was a cheater that helped out our rivals!”Jul 28, 2022; Boston, Massachusetts, USA; Radio personality, Joe Castiglione is handed a shirt by former Red Sox pitcher Roger Clemens during a ceremony honoring him after 40 years as the voice of the Boston Red Sox before the start of the game against the Cleveland Guardians at Fenway Park.