The qualities that helped Trump succeed in NY could be his undoing in DC


In the wake of the Manafort conviction and the Cohen plea deal, US President Donald Trump’s web of friends, loyalists and former lawyers, colleagues and campaign staff are all coming back to haunt him. The story is much larger than just an investigation that is pressing at the White House from multiple angles. It is also bigger than the notion that Washington’s insiders have simply taken revenge on Trump for winning an election he was supposed to lose (and one he did lose by the popular vote). It’s really a closer look at Trump’s own choices over the years.

The saga of Omarosa Manigault Newman, another Trump White House hire who went on to write a “tell-all” book and whose activities while she was employed are unclear, is another symbol of the bad choices Trump’s network made. The elephant in the room with her and others is “why were they hired in the first place?” In theory the answer is that team Trump didn’t have a lot of staff when they won the election and scrambled to hire anyone they could. Wait a sec. This is the same Trump that was featured in Art of the Deal right? This is the same person that appeared to be so successful in the 1980s and 1990s. Someone who was famous partly for being famous but was a keen crafter of his own image. So how could someone who prized himself a shrewd businessman and image expert, actually a brand genius, come to this?

In the film Nixon the character says “it’s the lie that gets you.” But with Trump its a lot more than a lie. Bill Clinton was also caught lying and he also had baggage from his years in Arkansas. But Clinton never styled himself the “art of the deal.” With Clinton it might be expected. He had personal foibles. Struggles between greatness and pettiness.

What emerges with Trump is that what is slowly sinking in during the White House years of his life is that the very qualities that made him successful in New York could be his undoing in DC. The qualities that appear to have made him successful were glam and glitter, a taste for media sensation, a keen understanding of New Yorkers, a crass, braggadocio, personal loyalties, family loyalties. All this served him well over the years. But in New York a web of such connections and behavior wasn’t a bad thing. It was able to cut corners, glad-handing over deals, browbeating people. NY of course had some kind of love-hate relationship with him. But in the end of the day, like lots of love-hate relationships that lead someone to success, it’s really more about secret love, while feigning dislike.

In this previous pre-White-House-life it might be unfair to say that forms of corruption were acceptable or paying hush money to people or hiring incompetents just to silence them, but certainly those were things that were more prized in certain circles. It’s a way of life for some people at a certain level that connects the underbelly of the business and political worlds in New York City. These are qualities that can be honed and prized within a kind of bubble within which NY is a kind of country and culture unto itself. Like those funny posters they sell in New York that show “the world according to New Yorkers,” or the iconic 1975 cover of The New Yorker ‘view of the world from 9th avenue.’

Flashy deals, people bragging over skirting the law or finding ways “around things” are an art. People love deals and complex connections and friendships and family, all tied together. It’s not like aspects of this subculture don’t exist outside of New York, but New York has chiseled them down. It grows out of the different groups that have made up the city over the centuries, the sub-cultures, the clannishness, the Wall Street Crowd, the intersection between different competing cultures and groups. And it’s not like it’s some secret. From Tammany Hall to the mafia, to historic legions of corrupt officials and others on the take, New York is famous for this. Trump grew up in these years of excess, born in 1946 and growing up in the post war years, the years of the mafia and the New York City blackout of 1977, the Koch years, Serpico, John Gotti. NY is also famous for all sorts of other things. But it’s not Iowa. And it’s not Texas.

How much did the qualities that made Trump so successful in the Big Apple help to undo him in Washington? There have been many outsiders in DC who became President. In fact they were almost all outsiders. Trump has been compared to Jackson, for instance. But the difference is that many of the other outsiders, whether Truman, Nixon or Clinton, had a ‘jungle guide,’ a term taken from Liar’s Poker, about Wall Street. If you want to go work on Wall Street and you were from Kansas you’d certainly find someone to help you find your way. An insider. An expert. In The Wire also a similar term is used for a “mentor” or protector in the police department. The term there is “rabbi.” So if you want to make your way in the police department you find a “rabbi.” In each profession and subculture there is this sense that you can’t really come in like a bull in a china shop and just destroy everything and play by your own rules. The only way that might be possible is if you were some genius with your own power structure. But Trump didn’t bring a power structure to Washington and he wasn’t some kind of genius with a knack for politics.

Trump came to Washington with his NY clan and a bunch of hangers-on of dubious qualities. Unlike other officials who slowly had to shed some of their local boys club when they got to DC, it’s not clear Trump ever attempted to do that. If you wanted to be good at business deals, as Trump supposedly was, you’d learn how deals and sub-cultures of deal-making work. But in Washington Trump didn’t seem keen on that at all. He didn’t want to learn to be like LBJ, or Reagan or anyone. His inner circle was made up of his people. The next circle was one of chaos and constantly changing lieutenants. Then there were the professional military people outside of that circle. Eventually the military people, like James Mattis and John Kelly, got closer to the center. The bizarro world of hangers-on from the campaign, like Bannon and the “Mooch” were pushed aside.

But what haunts Trump is not that. If the investigations into his affairs only covered what he has done since he came into office or since Kelly began insulating him, then the administration would be safe. But Trump is paying the price precisely for that crowd of people and weak links that were around him in NY. They are weak links because if the federal government wants to find something they will find something. If you’re wealthy you’ve definitely made an error somewhere on your taxes. And the people Trump worked with were not just wealthy, they were people who often thrived on the line between legality and corruption. Look closely enough and the Feds will “get their man.” In this case the investigators didn’t even have to look that hard. They’ve got plea deals and where they don’t they have a plethora of options on how and when to prosecute. Trump thinks it is about collusion, but he doesn’t seem to understand that it’s a lot bigger than that. Al Capone didn’t get convicted of being in the mafia, he go convicted of tax evasion. Nixon didn’t get convicted for bombing Cambodia, what got him was the lie. He resigned rather than face the long process of impeachment.

Trump never thought he’d be President, perhaps. At least those around him didn’t think he would. If they had, then people like Paul Manafort and Michael Cohen and others would have spent the last decade making sure their records were clean and going back and dotting the i and t of every tax form and bank account and foreign relationship. There wouldn’t have been payoffs to a woman or all sorts of strange side businesses. But there were, because up until November 2016, none of these people thought the whole weight of the federal government elephant would fall on them. And anyway, a lot of them had operated like this for years without problems.

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