we have to be honest - Ross Ulbricht has basically zero name recognition or figureheads close to Trump circa his 2016-2020 campaigns. 

Look at his inner circle then vs now. Maybe Patrick Byrne mentioned/knew of him? 

Certainly not Bannon, or Trump's kids

Now he has Ramaswamy + Massie in his ear, two lifelong libertarians that have fought for his cause for years

I don't think Ross was ever on the radar or he was even aware back then