After a successful college career, Tim Wakefield was drafted into the MLB by the Pittsburgh Pirates in 1988. Though he initially started out playing in the minor league, Wakefield ended up playing with the Pirates for two seasons before going on to join the Boston Red Sox in 1995. While playing for the Red Sox, Wakefield etched his name in the sands of time, racking up a total of 186 major league wins with the team. During his time with the team, Wakefield became popular for his signature pitch, the knuckleball. 

Following a wildly successful tenure with the Red Sox, Wakefield retired in 2012. "There have been many ups and downs along the way, but one thing is for sure, every time I stepped on that field I gave everything I had. All I ever wanted to do was win. And the bigger goal was to win a World Series for this great city. So, finally, after 86 years we were able to do that (in 2004) and the greatest thrill for me was to share it with all the players before us, but more importantly was sharing it with generations and generations of Red Sox fans," he said in his retirement announcement, per ESPN.

Beyond his professional achievements, the MLB legend also enjoyed a blissful family life with his wife Stacy Stover. According to CNN, the couple shared two children, Trevor and Brianna.

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