Chicago Cubs: Best first round picks of the past 25 years

Chicago Cubs: Kerry Wood

To this day, Cubs fans lament what might have been had Kerry Wood not had to deal with so many injuries throughout his career. Still, he had a distinguished career, most of which was spent with the Cubs, and that’s why he still deserves to be on this list.

With the fourth overall pick in 1995, the Cubs selected the big right-handed pitcher out of Grand Prairie High School in Texas. As many fans remember so well, he made a big splash right away when he arrived in the majors in 1998, throwing a complete game one-hit shutout while striking out a record-tying 20 batters against the Houston Astros in just his fifth major league start.

It was part of a 1998 campaign in which he won Rookie of the Year, winning 13 games while posting a 3.40 ERA and leading the league in hits allowed per nine innings and strikeouts per nine innings. Unfortunately, he then had to sit out the entire 1999 season due to injury.

When Wood came back, he was a trustworthy and reliable starting pitcher for a few years, including that incredible 2003 season in which he led the league in strikeouts. However, injuries started taking their toll again shortly after, and by 2007 Wood had to reinvent himself as a reliever. He was the team’s closer during the team’s 2008 NL Central Championship season.

Wood left for the Cleveland Indians in 2009 and also made a stop with the New York Yankees before finishing his career back on the north side of Chicago in 2011 and 2012, again as a middle reliever. Injuries aside, it was already an excellent career and ended up being a great draft choice.