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How late could someone enter the presidential race as an independent?

There are several third parties that might be ideal vehicles for a third party run. The trick is to get nominated by a party that already has ballot access. H.Ross Perot founded the Reform party and spent a lot of time and money getting the on the ballot. Subsequent "reformers" have grabbed onto that 'entitlement' and used to to their advantage. The Greens and Libertarians are the other two parties that have some ballot access. I think the Libertarians is the best. This might be the best year for the L's to nominate someone who is a billionaire and give it a shot.

I think one of the primary hurdles to third parties is not lack of ballot access (though that is obviously a hurdle) but lack of ability to get into the Presidential debates. In order to qualify, a candidate has to poll at 15%, which is tough to do without, as you noted, spending gobs of money.

There's a reason it is the BI-partisan commission on Presidential debates and not the NON-partisan commission on Presidential debates....