Round 1 - Pick 14
Who they took: Chris Williams, OT. There was no doubt the Bears needed an answer at LT, but Williams got off to an inauspicious start as he hurt his back in the Bears' second practice. He has turned into a solid guard, but injuries continue to plague him.
Could have had: Brendan Albert, OG/OT. Albert has improved every year and looks to be locked in as the Chiefs' starting LT going forward. A pair of OT drafted soon after, Gosder Cherilus and Jeff Otah have yet to live up to expectations.
Round 2 - Pick 44
Who they took: Matt Forte, RB. The Bears finally cut bait on Cedric Benson and needed a RB. Forte has proven to be one of the top RBs in football and, assuming they can come to terms on a new contract, should continue to be a key cog in the Bears offense.
Could have had: Ray Rice, RB. Although Rice was taken 10 spots later, he was the next RB taken and the Bears were said to be torn between the two. While Forte has been very good, Ray Rice has been better.
Who they took: Earl Bennett, WR. The Bears clearly needed to upgrade WR, and Bennett has proven to be one of Jay Cutler's favorite targets in the slot.
Could have had: Reggie Smith, S. Yes, Jamaal Charles was there too, but after Forte, no need for a RB. Smith is a decent safety for the 49ers, but the Bears were still better off with Bennett.
Who they took: Marcus Harrison, DT. Never lived up to his potential and was a bust with the Bears.
Could have had: next two picks were Jermichael Finley, TE and Cliff Avril, DE. Gulp.....After taking Olsen the year before, TE wasn't a need. However, imagine if it was Weddle in 2007 and Finley in 2008. Cliff Avril has turned into a Pro-Bowl caliber defensive end. The Bears whiff on their pick and their two division rivals hit home runs. Ouch.
Round 4 - Pick 120
Who they took: Craig Steltz, S. The Bears found a good special teams player and backup safety.
Could have had: Red Bryant, DT. Turned himself into one of the better run-stuffers in the NFL.
Who they took: Zack Bowman, CB. Started several games for the Bears, tended to get burned more often than not.
Could have had: Orlando Scandrick, CB. A solid nickel corner.
Who they took: Kellen Davis, TE. Lovie thinks he's going to be great, I'm not so sure. TE wasn't a need in this spot and they would have been better off going for more OL.
Could have had: Carl Nicks, OG. He was the next OL taken after Davis, and is now the highest paid OG in NFL history, and deservedly so. Another big "ouch".
Picks 208, 222, 243, 247 and 248
Who they took: Ervin Baldwin, DE (208), Chester Adams, G (222), Joey LaRocque, LB (243), Kirk Barton, OT (247) and Marcus Monk, WR (248). With so many picks in one round, you'd think they would hit on at least one. They didn't.
Could have had: Matt Flynn, QB (209), Stevie Johnson, WR (224) and Peyton Hillis, RB (227) were just a few late round steals where the Bears missed out.