Wakefield was the other member of those two World Series teams that was included in this year’s class. He was originally drafted as a first baseman by the Pittsburgh Pirates, but when a scout told him he’d never make it to the big leagues as a position player, he pivoted down the unorthodox path of converting himself into a knuckleball pitcher. Turns out that was a smart choice.
The Red Sox picked Wakefield up off the scrap heap after Pittsburgh released him and he paid immediate dividends. In his first year in Boston, Wakefield won 16 games and posted a 2.95 ERA, which was good enough to finish third in Cy Young voting that year.
Wakefield would spend the rest of his career with the Red Sox, ending his career as the franchise’s all-time leader in starts (430) and innings pitched (3,006). He is also second in appearances (590) and strikeouts (2,046), as well as third in wins (186) in Red Sox history. He’s the only pitcher ever to make at least 200 starts and 150 relief appearances for the Red Sox.
He only made one All-Star appearance and finished with an unspectacular 4.41 ERA for his career, but Wakefield endeared himself to Red Sox Nation with his reliability and versatility. He was prepared and willing to do whatever the team asked of him – whether it be starting, being utilized as a long reliever out of the bullpen, or even briefly serving as the team’s closer.
Wakefield has remained active within the organization after his playing days ended in 2011. He was named as the Honorary Chairman of the Red Sox Foundation in 2013, continuing his charitable efforts in the community that he was well known for during his career. He also serves as a Special Assignment Instructor for the Red Sox and has worked with fellow knuckleball pitcher Steven Wright.
Next: Larry Lucchino