I think the distinction between those who have "skin in the game" and those who survive on arbitrary indicators of prestige is an important one culturally , but especially as applied to Trump, I still think it's weird Taleb doesn't address any distance between perceived skin in the game and actual. Saying "Trump's a businessman who takes real risks, Krugman's just a writer who will never answer for mistakes" ignores…
Bankruptcy laws add a lot of value to a functioning capitalism and debtor and obliger are both aware of the laws. Perhaps you don't agree with them or Trump abused them but that's a different story.
Trump was smart in that he likely structured his financial dealings in a way to limit his personal losses, but the banks knew they and Incorporated that into their offer.
But it's true that more recently he has been a celebrity and leased out his name. However, since his name is his primary asset, you can still say he has skin in the game.
Also I would add that Trump's celebrity is due to something in his control. Whether it's because he's a demogouge, visionary or marketer extrodinaire, he is successful on his merits. Taleb would probably contrast that to some academic on an unelected government panel somewhere due to personal connections