The Very Stable Genius considers it "sport" to weasel out of financial obligations

I'll just quote extensively from this Quinn Hilyer piece at the Washington Examiner, because it pretty much says it all:

Donald Trump’s callous disregard for others is evident yet again in his series of Tweets on the morning of May 8 responding to the release of ten years of his embarrassing tax returns.

In particular, the most problematic Tweet was one saying this: “You always wanted to show losses for tax purposes....almost all real estate developers did - and often re-negotiate with banks, it was sport.”

No, Mr. Trump, it is decidedly not “sport” to leave others holding the bag for your own profligacy, recklessness, and gaming of the system. And “renegotiating” with banks to ask them to eat many of your own losses is understandable as a last resort, but not in the slightest bit excusable as a deliberate strategy.

Has the VSG considered the ripple effect of this "sport"?

The banks, if publicly held, involve the investments of perhaps tens of thousands of Americans, many of them small investors, many of them pensioners. The share prices of those banks drop when the banks write off big losses. The effective savings of those small investors are depleted.

Worse, when an entire cohort of real estate speculators like Trump act as if they are “entitled” to take “massive write offs and depreciation,” it causes systemic crises. Indeed, it was precisely the radical gaming of the system that Trump and others engaged in during the late 1980s period covered by his leaked tax returns that caused the massive savings and loan crisis, which roiled the entire American economy.

While silver-spoon speculators like Trump were engaged in “sport,” millions of Americans lost jobs and tens of millions experienced wages lower than they previously had expected. 

It's a near-certainty that he's the only 2020 alternative to what the post below deals with, but let's harbor no illusions about what he is as we draw closer to that time.