No way in hell for 2020 but if Trump could theoretically replace Ginsburg, Thomas and Breyer on the Supreme Court in his second term and Cuban is lined up against a Lindsey Graham, Jeb Bush, Mitt Romney, then yeah I could see myself voting for Cuban.
Tech savvy, creative business guy with a bit of a libertarian streak.
As far as the courts, I don't think his appointments would be too much of an issue (plus voting trends favor the Republicans in regards to the senate over the next decade so you would likely have a McConnell type to keep him in check).
I consider myself just slightly right of center so a guy like that could be palatable and a bit of fresh air versus some of the more spineless, disingenuous, establishment types we have been forced to stomach before Trump came along and shook things up.
