1. 200th Career Win
Wakefield himself may not have agreed with this, but his 200th (and final) win was easily the crowning achievement of his career.
You have to last a long time in the major leagues to win 200 games, after all, and you don't stick around that long if you're not good. Certainly nobody could have imagined Wakefield getting to 200 wins when he joined Boston as a 28-year-old reclamation project in 1995 after washing out with the Pirates.
But Wakefield stuck around for a long time. He was good, flexible, unique, and always willing to do whatever the team needed to help them win.
Most years, he was a frontline starter who soaked up 200 innings in the rotation, taking the ball every fifth day without complaint. He spent a lot of time in the bullpen, too, making 164 career relief appearances. Sometimes as a long man, sometimes as a middle reliever and sometimes as a closer, he was almost always available.
By 2011, however, Wakefield was clearly fading. He was 44 and his ERA was over 5.00 for the second year in a row, so his career was nearing the end.
He entered the season only 7 wins shy of 200, but getting there took a lot longer than expected. He earned his 199th win on July 24, but stayed stuck there for the rest of the summer. September rolled around, and he was running out of time.
On Sept. 13, he finally got it. The Red Sox blasted the Blue Jays 18-6 at Fenway Park, giving Wakefield more than enough run support to earn the W. He wasn't at his best that day (6 IP, 5 ER), but he pitched well enough to win.
And if that isn't the perfect summary of Wakefield's career, then I don't know what is.