If you were a chief political operative...

[Notre Dame rules!]

Jeb Bush/J.C. Watts

You would have to assume that Jeb carries every state that Dubya carried.  Being Catholic, (a real one, not like Kerry) Jeb would also have a better chance at taking WI, MN, MI, and NH.  It would also help strengthen his margins in IA, NM, AZ, and CO, and shave the margins down in places like IL, and the North East.

The inclusion of J.C. Watts (a very charismatic, conservative Af-AM) would help put IL even more into play and could help shave of the NYC vote from Dems in NY.  His being on the ticket would also help in places like MD and NJ.

Jeb's Columbian born wife, and his fluency in Spanish, could very well negate any potential VP candidacy of Richardson.  Jeb's Latino connections could shave the margins down somewhat in CA. 

I figure that a well run campaign could net the GOP 40-45 states.

[Notre Dame rules!]

The only way you can beat Jessie Jackson is to be as rude to him as he is to you.  I doubt that J.C. would stoop to that level.  Did Jessie even let him answer a question without constantly interrupting?

I used to follow J.C.'s  career in the Congress, and watched him campaign for Dubya in this past election.  I found him very impressive, though I have to admit that I didn't see the debate with the "Reverend" Jackson, so I'll take your word for his performance at that forum.