Most Cy Young Awards (Seven)
Athlete: Roger Clemens
When: 1986, 1987, 1991, 1997, 1998, 2001, 2004, 2004, 2005)
Similar to Bonds' situation, the career of Roger Clemens is shrouded in mystery over cheating allegations, which makes his accomplishments, like his seven Cy Yong awards and Game 4 performance in the 2000 ALCS where he struck out a record 15 batters in a one-hit game, slightly tainted in the eyes of the public.
When the Mitchell Report was released in 2007, Clemens' name showed up alongside allegations of anabolic steroid use late in his career. Eventually, the matter was taken up by the U.S. District Court in Washington, D.C., which accused Clemens of perjury, false statements and obstruction of Congress. In 2008, prosecutorial misconduct led to a mistrial and four years later, Congress found Clemens not guilty on all counts of lying about never taking performance-enhancing drugs. *cues the soundtrack*