I say a little bit of everything. The Bears had experience success with FA o-linemen and finding FA offensive talent that did produce albeit for a short period time. It was this over confidence in their FA picks which lead them to believe they could cheat the fates and draft what they thought was the best players available. As for the legitimate madness remember in the playoffs it wasn't the offense that was expose it was the secondary and defense that was expose. So they gambled and went defense heavy again to try and win it all...but they came up short with only a superbowl appearance.
I would argue that the bears wouldn't have made the superbowl if it wasn't for the contributions of Devin Hester, Mark Anderson, and (sigh) yes even Daniel Manning. So in a sense JA's gamble to work... to a point. A superbowl appearance is nothing to be taken lightly. The bears may still be able to get 3-4 starters from this draft and that is considered a successful draft by any standards.
I still consider the 2006 draft a success...it's the 2007 that I found to be appalling, but that's a whole other can of worms.