Tim Wakefield played 19 years in the MLB, 17 of which were with the Boston Red Sox; where he won two World Series rings and played a crucial role in the pitching rotation year in and year out.
Wakefield was drafted as a second basemen in 1988 by the Pittsburgh Pirates, but was told that he would never get above double-A with his skills. He then decided to develop a knuckleball so that he could say he did everything he could to make it.
By 1992 he had made it. In his first game getting called up to the bigs, he threw a complete game, striking out 10 batters against the St. Louis Cardinals. He would go on to win National League Rookie Pitcher of the Year by compiling an 8-1 record in the 13 games.
However, his next season was far from the same as he struggled early and was sent down to the minors where he would stay for all of 1993 and most of 1994. The knuckleballer was later dropped by the Pirates, and picked up by the Red Sox shortly after.
Wakefield played three games in Pawtucket and never looked back. He pitched in 27 games his first year in Boston, and eventually 590 games over his long career in Boston.
In his first five campaigns with the Red Sox, he won 71 games and had an ERA of 4.53. However, he would not achieve his ultimate goal of winning a World Series until 2004 at the age of 37. Wakefield won 12 games and lost 10 that year with a 4.87 ERA. But, it was his leadership in 2004 that he would be known for.
During Game 5 of the 2004 ALCS, he entered in the 11th inning tied at four with elimination on the line. He went on to pitch three scoreless innings before David Ortiz ended the game with a single in the bottom of the 14th. The Red Sox would sweep the Cardinals to win their first World Series in 86 years thanks to the help of Wakefield.
The next season, he led all Red Sox starters with 16 wins and a 4.15 ERA at the age of 38. Wakefield would go on to win one more World Series in 2007, but was left off the series roster due to a shoulder injury. That year he won 17 games for the Red Sox helping the team to win 96 games and an AL East crown.
His last season in the MLB was 2011. The then 44-year-old appeared in 33 games and posted a 7-8 record before calling it a career.
Wakefield moved back home to Florida for a year with his wife and two kids.
Wakefield is known not just for his pitching, but also for his philanthropy. He was nominated for the Roberto Clemente award eight times by the Red Sox for his charitable work off the field and won the award in 2010. The former pitcher moved back to Massachusetts soon after and started working as an analyst for NESN in 2012, and has worked for them ever since.