Timothy Stephen Wakefield (August 2, 1966 – October 1, 2023) was an American professional baseball pitcher renowned for his mastery of the unpredictable knuckleball. After being drafted by the Pittsburgh Pirates as a first baseman in 1988, he reinvented himself as a pitcher and burst onto the scene in 1992, winning both of his starts against Tom Glavine in the NLCS. However, he is most celebrated for his 17-year tenure with the Boston Red Sox, where he helped secure World Series championships in 2004 and 2007 and became the oldest active player in MLB when he retired at age 45. During his career, he achieved his 200th win in 2011, and he ranks third in Red Sox franchise history for wins (186) while holding the team's all-time record for innings pitched (3,006). A two-time All-Star (2009) and winner of the Roberto Clemente Award in 2010, Wakefield's remarkable longevity and dedication left an indelible mark on the game.