Clemens's seven Cy Youngs across four teams

Clemens won his Cy Youngs in 1986, 1987, 1991, 1997, 1998, 2001, and 2004. The 1986 and 1987 came with the Boston Red Sox at age 23 and 24 — making him the first pitcher to win consecutive Cy Youngs in the AL. The 1991 came in a 4-year-gap year, also with the Red Sox. The 1997 and 1998 came with the Toronto Blue Jays after Clemens left Boston as a free agent. The 2001 came with the New York Yankees. The 2004 came with the Houston Astros at age 41 — the oldest Cy Young winner in baseball history.

What’s structurally unusual is that Clemens won Cy Youngs across four different franchises. No other pitcher in baseball history has won the award with even three different teams. Greg Maddux won 4 in a row (1992-95) but split between the Cubs and Braves. Randy Johnson’s 4 straight (1999-2002) were all with the Diamondbacks.

How the career-Cy-Young leaderboard stacks up

After Clemens (7), the all-time leaders run: Randy Johnson 5, Greg Maddux 4, Steve Carlton 4, Sandy Koufax 3 (consecutive 1963, 1965, 1966), Pedro Martinez 3, Tom Seaver 3, Justin Verlander 3 (2011, 2019, 2022), Jim Palmer 3, Max Scherzer 3, Clayton Kershaw 3.

The modern era’s most-decorated pitcher is Justin Verlander at 3 (winning at age 28, 36, and 39 — the largest age gap between Cy Youngs ever). Among active pitchers heading into 2025: Verlander 3, Kershaw 3, Scherzer 3, Jacob deGrom 2, Shane Bieber 1, Sandy Alcántara 1, Spencer Strider 0. The structural pace of modern Cy Young races (favoring relief-fueled bullpen games + 6-inning starters) makes it harder for any pitcher to dominate seasons enough to win 5+ awards.

Clemens and the Hall of Fame

Clemens has been on the BBWAA Hall of Fame ballot for 10 years (2013-2022) and never received the 75% needed for induction — peaking at 65.2% in 2022, his final year of writers’-ballot eligibility. The Mitchell Report (2007) named him as a steroid user; he denied the allegations under oath in front of a House committee in February 2008 and was charged with perjury. He was acquitted at trial in June 2012.

His statistical case is overwhelming — 354 wins, 4,672 strikeouts, 2.21 career WHIP, 7 Cy Youngs, 11 All-Star selections. He’ll be eligible again via the Era Committees (formerly Veterans Committee) starting in December 2025. The Hall of Fame’s character clause — the implicit reason for his exclusion — has become the defining issue of modern baseball historiography. Until those committees vote him in or definitively decline, his official status remains ‘eligible but not elected.’

Background facts cross-referenced with the Wikipedia article on Roger Clemens and Pro-Football-Reference / Basketball-Reference public records.