The Cubs' First Round Failures

Yup, we're going to talk about the Cubs' drafts again. I suppose you can think of this as a companion piece. Because while I was putting together and writing the All Bonus Baby Team piece for the Cubs, I was startled by the lack of first-round talent that even showed up on my radar.

Let's just go over this quickly, because this is just as tormenting for me as it's going to be for most you. But to begin this tale, we're going to go all the way back to 1991. That year, yours truly entered the world as a wee baby, and the Cubs used their first-rounder on Doug Glanville. Since then, Chicago's had about as much luck with first-round picks as they've had with winning World Series championships over the past 101 years (baseball burn).

From 1992 through 1994, the Cubs had five first-round picks. Three of them came in 1993, and each draft saw the Cubs pick in the top-15. The best player to come out of the bunch was shortstop Kevin Orie, who peaked in 1997 as the Cubs' third baseman, posting 2.5 WAR thanks to a decent bat and strong defense. He struggled the next year and was effectively out of the majors by the end of the 1999 season.

Then the Cubs had an interesting little run from 1995 to 1998. They landed Kerry Wood with the fourth overall pick in 1995, Jon Garland with the tenth overall pick in 1996, and Corey Patterson with the third overall pick in 1998. We know the stories of these guys pretty well. Wood looked like a future Cy Young winner after a ridiculous rookie season and multiple years of elite prospect status, but had his career derailed by injuries and only made more than 28 starts in a season twice. Garland turned in a few very good years for Chicago's crosstown rival, but has ultimately been a mid-rotation pitcher for the vast majority of his career. And Patterson, for all of his incredible tools, could never quite put it together as a hitter after being shoved into the lead-off role by the Cubs, and eventually has become a journeyman bench outfielder. You wouldn't call any of these picks bad, and Garland and Wood in particular had years when they were legitimately among the better pitchers in baseball, but it's hard to build championship-caliber clubs when these are your first-rounders.

Then comes a truly dark period of drafting the Cubs, reminding all Cub fans who were dissatisfied with their recent first-round picks that things could in fact get much, much, much worse. With consecutive top-3 picks in 2000 and 2001, the Cubs snagged shortstop Luis Montanez and right-handed starter Mark Prior. Montanez took 8 years to reach the majors and may not come back after a couple years of weak performance. And Mark Prior, god damn. He was cool. But after witnessing his 10-strikeout MLB debut at Wrigley in person and getting him to sign my glove at a game later that season, I'm kind of bitter about Mark Prior. So let's move on.

The next four years saw six consecutive first-round picks that never even saw the majors: Matt Clanton, Chadd Blasko, Luke Hagerty, Bobby Brownlie, Ryan Harvey and Mark Pawelek. The latter three were all regarded as legitimate high-quality prospects, but all sputtered out as they closed in on the big leagues. And then in the winter of 2005, the Cubs finally changed scouting directors, bringing aboard current director Tim Wilken.

And since then, we've seen a lot of potential. Outfielder Tyler Colvin, Wilken's first pick with the Cubs, posted a .246 isolated power in part-time duty with the Cubs last year and has the potential to become a very good regular. 2007 first-rounders Josh Vitters and Josh Donaldson shouldn't be considered busts; Vitters is a tough prospect to gauge but he's still a 21-year-old with a swing that scouts adore, and Donaldson helped Chicago to acquire Rich Harden, who was a key piece for them in 2008.

Since then, it remains to be seen what exactly to think of Chicago's first-rounders, but early indications are good. 2008 first-rounders Andrew Cashner should return to the Cubs' rotation once he comes off the disabled list, and he has legit top-of-the-rotation potential assuming he has the durability to go 180+ innings every year. 2009 first-rounder Brett Jackson is one of the best outfield prospects in the game, and should supplant Marlon Byrd as the Cubs' center fielder at some point in 2012. And 2010 first-rounder Hayden Simpson may have shocked people by going as high as he did, but Chicago's scouts loved this guy and his stuff really played up as the spring wore on going into that draft.

So if you're wondering why the Cubs' All Bonus Baby Team looks so weak, don't think that it's due to a lack of getting luck with hidden gems. Between guys like Geovany Soto and Sean Marshall, the Cubs have found their fair share of those. But almost every team needs to have some premium amateur talent reach its potential, and that's something that hasn't happened very often for the Cubs, which obviously explains why they've had to foray into the free agent market with such frequency.

But things have appeared to improve since Wilken's come aboard, and the early returns on key Wilken picks, like Colvin, Cashner and Jackson, have been pretty good. And it would be silly to ignore Chicago's strong presence in Latin America and on the Pacific Rim, where few if any teams can match their pull. As you've been able to see with guys like Starlin Castro and Hak-Ju Lee, the Cubs are unearthing elite talents through those avenues as well. But teams can't afford to eschew the draft if they want to build an elite organization from top-to-bottom, and especially teams with the kind of spending power that the Cubs have.

Chicago picks No. 9 in this year's draft, so they're likely to get an elite talent given the depth of this draft class. If the past couple years have been any indication, Cubs fans should have faith in Wilken and the Cubs' scouting team to land a very, very good prospect at that position. But if you ever wonder why they're so damn negative about all of their young players, you can always bring up Prior, Patterson, Montanez, Harvey, Brownlie and Pawelek and they'll probably remind you.