A few reasons why Trump went for "the Big Con,"

[no_hypocrisy]

namely bilking the U.S.A. while President.

1. He's good at it. He's been doing it on a small stage all his life. He was playing "The Palace" once he was elected in 2016.

2. Trump is a keen consumer of media. He watches more television and cable than people hired by the networks. He knew his audience(s).

3. Trump looked to see what had worked before 2016. Stuff like how Kim Kardashian milked her 5-minute wedding and marriage for two days on the E-Channel. She got lots of money for advertisements. She got lots of attention. And she was forgiven when she had enough with Kris Humphries. Trump saw that and rhetorically said "How hard can that be?"

4. Same thing with the Bravo Housewives Franchises. Some really bad behavior and yet these women have staunch fans no matter what they say and do.

5. To do a con, you need a mark who doesn't catch on that you've robbed him. Enter the RWNJs, the Evangelicals, the Kochs, the Birchers, the gun nuts, And Trump's still robbing them today.

6. Trump cheats, even he doesn't have to. Exhibit One: golf

In other words, the "Board" was set

[Hugh_Lebowski]

1. The simple fact he's been a conman his entire life is the most illustrative

However the support he knew he had coming from Russia played a role too I think ...

[Grasswire2]

2. Google says he searches himself sixteen times a day.

Weirdo.

[-misanthroptimist]

4. I certainly hope he has clicked on some of the things I've said about him.

[calimary]

7. Only 16 times a day?

I would have guessed maybe five hundred 16 times a day. Or at least five dozen.

[leftieNanner]

3. Plus he's likely broke!

He needed the cash.

Got some big debts coming due soon.

Sucks to be you Donnie!

[ProfessorGAC]

5. Debt Service On Normal Term Loans...

...was already oppressive.
Now that he's toxified his "brand" revenues have plummeted, asset value has fallen, making debt to equity untenable for new lenders.
The loans you're talking about that are on top of debts his organization could barely cover.
Given the layers of debt, it appears he was borrowing against inflated asset values to cover the payments on debt already existing.
A grand version of check kiting.

[leftieNanner]

6. Won't it be wonderful

to see Trump Tower on the auction block for pennies on the dollar!

You can only pay one credit card with another one (ad infinitum) for so long.

[jaxexpat]

8. It's a variation on the Bartcop rule # 1.

If a person makes a "mistake" and profits by that "mistake", expect them to continue making that same "mistake" as often as possible. In this case it goes, "if a conman who considers the whole world his "mark" succeeds with one of his harebrained schemes, expect him to continue milking that sucker forever."

[Grasswire2]

11. Bartcop.

[jaxexpat]

12. Aye.

[Harker]

9. The board was set...

or the bowling pins were set, and he had plenty of balls.

[monkeyman1]

10. how bad can it be when bank's classifying you & company a huge risk !!!