Why is Jim Hendry so bad at drafting?

Can someone please explain to me how Jim Hendry, a former Director of Player Development, is so bad at drafting players to develop? There are, sadly, no stats to answer this question available on Fangraphs. Maybe BP has worked out a metric by now to explain this, but I am currently unaware of such a metric.

Since the Cubs promoted Hendry to GM (2002), he has not selected a single quality first round draft pick. Is this the Curse of Mark Prior? Take a look at who the Cubs drafted and who they passed up to get them over the past 7 seasons and you will see why the Cubs have absolutely no minor league depth:

2002: Bobby Brownlie (who?)
Passed over: Joe Blanton, Matt Cain, Joey Votto, John Lester, Jonathan Broxton, Curtis Granderson

2003: Ryan Harvey (who?)
Passed over: Nick Markakis, John Danks, Aaron Hill, Chad Billingsley, Carlos Quentin, Adam Jones, Andre Ethier, Sean Marcum
Of interest: the Cubs did draft a quality hitter in Jake Fox, but he is a DH at large in the NL...

2004: The Cubs gave up their 1st round draft pick to sign Type A free agent LaTroy Hawkins
Passed over: Yovanni Gallardo, Dustin Pedroia, Jonathan Papelbon, Adam Lind

2005: Mark Pawelek (who?)
Passed over: Nolan Reimold, Kevin Slowey, Jacoby Ellsbury, Matt Garza, Colby Rasmus, Clay Buchholz, Michael Bowden

2006: Tyler Colvin (eh...)
Passed over: Travis Snyder, Daniel Bard, Chris Coghland, Joba Chamberlain, Brett Anderson, Chris Tillman, Justin Masterson,

2007: Josh Vitters (2.4% walk rate in the minors, can't hit A ball pitching)
Passed over: Matt Wieters, Matt LaPorta, Rick Porcello, Jordan Zimmerman, Jason Heyward, Julio Borbon, Aaron Poreda

2008: Andrew Cashner (a middle tier relief pitcher? really? in the first round? ugh...)
Passed over: Daniel Schlereth (a much, much, much better relief pitcher)

This isn't the case of a bust or two, but a pattern of poor decisions. A small few of the Cubs later round picks have been decent (Notably Ricky Nolasco and Jake Fox), but the Cubs tend to either trade those players away or let them toll away in the minors until they are basically 30 (see Randy Wells, Micah Hoffpauir). We can only hope the Cubs' 2009 pick, Brett Jackson, won't continue the curse.

The sad part of this all is that the Cubs have one of baseball's top payrolls and the organization simply squanders its resources. The Cubs are like the Yankees from 2002-2008. Wasteful spending, poor drafting and bloated contracts. The only difference is that the Yankees can spend a bazillion dollars a year and afford to make as many bad contracts as they want. They'll just up the cost of a ticket to $4,000. The organization needs a breath of fresh air in the front office and that means canning Hendry and starting anew. Hendry has made some great acquisitions for the Cubs (Derrek Lee, Aramis Ramirez, Rich Harden), but he's also given away more than his fair share of quality players for absolutely nothing in return (Michael Wuertz, Ricky Nolasco, Felix Pie, David Aardsma) and filled the team's holes with junk (Aaron Miles, Kevin Gregg, Neil Cotts, et. al). The Cubs desperately need someone who knows how to spend money and spot talent so that in 2 years, when all of the Cubs bloated contracts are off the books (except that of Soriano, who is signed until he is 52), the organization can start anew, rebuild and contend with confidence. Any suggestions of who's out there?