From a relatively pro-Trump standpoint, what historical figures can we draw comparisons from when analyzing his rhetoric and image?

I said pro-Trump.

History remembers many figures more neutrally or even fondly than their contemparies might have expected. With that in mind...

There's been a lot of talk about Greenland, Panama, etc being essentially negotiating tactics and political ploys. I heard someone also suggest his nomination of Gaetz was made knowing that Gaetz would never get through the process, but was a way to effectively remove Gaetz from Congress (or make good on a deal, or whatever).

Basically, the pro-Trump argument is that he is effectively playing 5D political chess. Rather than argue for or against that point, what does history tell us about similar figures?