Best positional player: Adam Everett (1995: Round 4, Pick 91)
The Cubs’ unsigned pitcher selection pool is barren. Instead, I offer two players they signed, drafted, then quickly traded. First, Jon Garland (1997: Round 1, Pick 10). He was drafted on June 3, 1997 and traded on July 29, 1998 for Matt Karchner. Now, not to judge, but Matt Karchner was 31 years old, and had one season with 50 or more innings and a sub-4.5 FIP or 3 ERA to that date – yes, he was a reliever. Garland hadn’t pitched great in the minors that season. Mind you, he had a 5.03 ERA and a 1.56 SO/BB ratio in 107 innings, but the Cubs had just taken him in the top 10 of the draft. Couldn’t they find someone else at least slightly enamored of him and gotten a better return?
Best positional player: Andy Tracy (1995: Round 28, Pick 783)
Best pitcher: Trevor Hoffman (1989: Round 11, Pick 290). Not only did Hoffman sign with the Reds, but he played for them through the 1992 season. It was at that point the Florida Marlins drafted Hoffman in the expansion draft.
Honorable mention: Jeremy Sowers (2001: Round 1, Pick 20). Notable because the Reds never intended to sign Sowers, instead opting for a supplemental pick the next year. It looks like a bad decision, not because Sowers is a maven, but because in doing so the Reds missed out on Jeremy Bonderman, David Wright, and John Rheinecker’s beard.
The Astros are actually a special case. They have not one connection to the top talents of the 2010 draft, not two, but three. Derek Dietrich, Chad Bettis, and Brett Eibner were all drafted and went unsigned. Now each may go in the top two rounds with at least one likely to go in the top 30. Houston’s farm system has been scorched ground for a while now, and while there’s no guarantee that any of those players turns into a legitimate prospect it certainly would’ve made their system look healthier.
Best positional player: Jason Giambi (1989: Round 43, Pick 1,118). Drafted as a shortstop, Giambi would head to Long Beach State University and later the Oakland Athletics on his way to national prominence.
Best pitcher: Andrew Bailey (2005: Round 16, Pick 475). Did you know that with his last appearance – career number 89 – Bailey became Wagner College’s all-time leader in games pitched? Take that Al Severinsen.
Honorable mention: Kanekoa Texeira (2004: Round 31, Pick 916). Mostly because of his name and he’s in the news.
Best positional player: Stephen Drew (2001: Round 11, Pick 324). Didn’t sign and signability issues caused him to sink in the 2004 draft, too.
Best pitcher: Chris Young (2000: Round 3, Pick 89). Actually did sign with the Pirates, and was traded alongside Jon Searles in December of 2002 for Matt Herges. Hey, anytime you can flip a 23-year-old with strikeout-to-walk ratios of 3.6 and 4.00 in more than 200 minor league innings for an aging middle reliever, you have to do it, right?
Honorable mention: Willie Harris (1996: Round 28, Pick 816)