If in June or July 2015 that guy had said, "look, I have money. I don't need to do this,"

[mahatmakanejeeves]

he'd be running his golf courses and his properties now, and he wouldn't have a care in the world.

Full disclosure: if you're looking for someone who is immune from making bad decisions, I am NOT the droid you are looking for. But wow, has that guy made some real world-class boneheaded decisions.

[Irish_Dem]

1. It was said that he ran initially to just strengthen his brand.

And he was surprised when Putin put him in the WH.

[Claustrum]

2. I still maintain that he was broke and he needed the money from campaigning.

He never expected to win the republican primary, let alone the presidency.

[rurallib]

5. I have heard the theory that he was so deeply in debt to Russians (Putin?)

that this was what Putin wanted in return.

[RockRaven]

3. If he had taken his inheritance from Fred Sr and plopped it into S&P500 index funds he'd be

several times wealthier than even his wildly bullshit claims of net worth today...

So, yeah, he's had a lot of missed opportunities for peace and quiet and luxury which have been sabotaged by his dumb mob brain and raging narcissism.

[mahatmakanejeeves]

4. Yes, I've read that. He should have mailed the money to Vanguard and gone golfing. NT