Boston Red Sox: 10 biggest first-round draft pick disasters

Red Sox 2000 Draft

No. 22 – Phil Dumatrait
No. 29 – Adam Wainwright (Braves)

Here we have another failed Red Sox draft pick who at least made it to the majors. Like Everett before him, Phil Dumatrait was no longer with the Red Sox by the time he made his big league debut in 2007. Unlike Everett, Dumatrait didn’t find modest success at this level. He was 4-13 with a 6.20 ERA in 87 career appearances with three different teams and he hasn’t appeared in the majors since 2011.

Shortly after the Red Sox wasted a pick on Dumatrait, the Atlanta Braves selected Adam Wainwright. The Braves made a mistake of their own by trading Wainwright to the St. Louis Cardinals for J.D. Drew in 2003. Despite that Boston handed Drew a lucrative free-agent contract a few years later, let’s pretend that they wouldn’t have been foolish enough to make that trade.

Wainwright has had a successful 14-year career with the Cardinals. He made three All-Star appearances and finished top-three on the NL Cy Young ballot on four occasions.

He can do more than just pitch. Wainwright has a pair of Gold Glove awards and a Silver Slugger on his mantle.

The 37-year-old is under contract with the Cardinals for 2020 and it’s unclear if his career will continue beyond that but he’s certainly done plenty to earn his first-round draft status.