The fact is that any Republican, no matter how good he is, is going to start out with a severe handicap--being a Republican in a Democrat state.
With that in mind, any Republican candidate is going to have to be twice as good at everything than his opponent. Most importantly, he'll have to have a clear agenda that appeals to a broad spectrum of voters, and he'll have to be able to communicate them effectively. He'll have to have twice as much charisma, twice as much charm, and have twice the one-on-one people skills as the Democrat. He'll have to run an upbeat, positive campaign. He'll have to work twice as hard. And sadly, but realistically speaking, he'll have to be able to attract twice the money--which means he'll have to already have some name recognition going into the campaign.
I don't know if Simon had any or all these things, since I didn't really follow this race. But I do know that even from 3,000 miles away, it didn't look good with that whole campaign contribution photo thing, and being "exonerated" in court was even worse. A candidate going through legal proceedings during a campaign is a disadvantage any way you look at it.
Simon's team may or not have been the absolute best, but they had too many negatives to overcome, IMHO.
The sorelosers blaming Bush