Elections are won by those with the best funding sources, providing their funding sources are significantly stronger than those of their opponents. If funding is relatively equal on both sides, then other factors will determine the winner.

McCaine never had a chance. Given the general situation in 2008, which was not favorable to the Republicans anyway after 8 pretty disastrous years of George Bush and an economy going down the toilet bowl, he'd have needed quite a bit more funding than Obama to win. And he had considerably less funding than Obama. Obama also left Hillary behind in the funding drive. The one thing he had to overcome was being "Black", but that had its advantages too, in certain respects...it just depends on how you look at it. There's a right time for everything. Hillary could use the fact that she's a woman to her advantage...if the time was right, and if she handled it right. Same goes for Sarah Palin.