I have to say I admire your positive attitude towards 2020. I have serious concerns that Trump can pull off another win.
The Dems, in large part, seem to encourage this outlook and I pray that I am absolutely wrong. I am not sure we can actually survive another Trump/Putin 4 years.
My recollection was Bill more or less said that if you want to run, run. Back in those days the Trump's and Clinton's were friends. I don't think Bill encouraged Trump to run. But I would imagine Bill's thinking was that if Trump ran, he might disrupt the GOP primaries some, thus making it easier for Hillary to win.
I don't think Bill, Hillary or Trump himself way back when thought Trump had one iota of a chance.
My take on it anyway.
It's high past time that we start electing Americans to congress and the presidency who put America first instead of their political party. For way too long we have been electing Republicans and Democrats who happen to be Americans instead of Americans who happen to be Republicans and Democrats.