2010?
Normally they don't get 60 in the Senate though, which means that the system is working at intended (you need to stay consistently popular for 6+ years to start swinging the Senate).
How much of his agenda is really his, anyway? He's a punching bag to distract everyone while the real power players get their way.
Many smarter people with more money and better connections failed, see e.g. Bloomberg.
You could also think of it as, "Those with enough money and power to influence who gets elected president are good enough at the game to get Trump elected president."
Check Scott Adams’ writing on Trump’s persuasion abilities.
When did Mexico agree to pay for the wall?
Plus he's a construction magnate -- get enough traction to get a preliminary budget and start allocating funds to his buddies. Even if it's just a concrete wall for 1/3 of Texas that's big $$$ for his construction cronies.
He's like a vacuum cleaner salesman who can always get his foot in the door, but can never manage to sell a unit.
He's like a vacuum salesman who promises to give his customers dishwashers and toasters for free if they buy a vacuum cleaner.
When they buy the vacuum cleaner, it turns out he lied about the other goods but they still ended up with the vacuum cleaner. But what a lot of people really wanted was the dishwasher.
I may have pushed the analogy a little too far...