Wakefield, a native of Melbourne, Fla., began his professional baseball career in the ’80s. The Pittsburgh Pirates originally selected him as a first baseman in the 1998 draft. He later became a pitcher, developing and perfecting the rarely thrown knuckleball, and played for two minor league teams until he was called up to the majors as a pitcher for the Pirates in 1992.
Three years later, he was released and signed as a free agent with the Red Sox, for whom he pitched for 17 seasons until he retired at age 45 as the oldest active player in the MLB at the time.
During his time with the Red Sox, the team won two World Series, most recently in 2007. In 2004, they beat the St. Louis Cardinals in the championship, marking their first World Series victory since 1918 and breaking what fans called the “Curse of the Bambino,” named after MLB legend Babe Ruth, who was traded from Boston to the team’s arch rival, New York Yankees.
Wakefield, a 2009 All-Star with the Red Sox, was inducted into the team’s Hall of Fame in 2016.