He'll be too old, 74 years old by then, that would be the oldest person to run for president.
Beyond that, his business brand is taking a beating, occupancy in Trump branded hotels is down so much that they're now changing the name to "Scion" in many locations, lol. He won't want to do this again, it will destroy whatever is left of his so-called "brand". I'm sure his kids and business partners are in a lot of ways just want this whole thing to end already.
The problem with the Republicans is the demographic tide is against them. They cannot continue to run campaigns based on alienating "minorities" ... not when "minorities" are becoming the majority voter block. Every 4 years more old people die (and those are mostly old Republicans) and more young people become eligable to vote (and 50% of younger America is an ethnic minority). They also have huge issues with college educated whites, there's also so much hay you can make with rural voters.
Even solidly Republican states like Georgia, North Carolina, and gulp maybe even Texas are started to turn purple instead of rock solid red, Republican party needs to adapt or they will face continual routs.
Trump screwed them over this campaign, if Marco Rubio was the candidate he probably would've won.
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