Great analysis of Jordan's response to Cathy. I think perhaps one of the reasons he didn't address her 'deeper questions' is perhaps because she was unwilling to go there. It would have been obviously fantastic if he were able to do that, but I think he did really well considering the time that was allotted to them and the combative stance she assumed right from the beginning. I think he was also probably searching for a win and felt somewhat vindicated when finally she was stumped.
From remembering H3H3's interview with him a few weeks later he recalled how 'bait-and-switched' he felt. Apparently she was lovely backstage then turned on him as the interview started. This would explain why he was so taken aback to begin with, then started 'sparring' with her as they got on with the interview some more.
All in all however - great analysis dude! Really enjoyed it and hope it will help me in my work and interactions with people!