A few months ago I mentioned in one of my stories that one of Donald Trump’s golfing pals, Steve Witkoff was a shocking choice to me as the new Middle East negotiator on the Israeli/Gaza situation. I likened in to the equally shocking choice of Jerrod Kushner for that role in Trump’s first administration. Of course, Jerrod got what he wanted from the gig after the Emirates and Saudi Arabia (via his big bud, MBS) gave him $2 billion to play with, so Jerrod decided to stay home during Trump 2.0 in order to became a private equity guy. So now it’s Steve Witkoff’s turn, but Witkoff already has his own $2 billion, so his motivation is a bit less clear.
I got to know Steve Witkoff during my real estate restructuring days in 2009-2010 and it is very hard for me to imagine him negotiating anything complex or delicate for America. He’s a typical successful real estate developer, which isn’t necessarily bad, but diplomacy would seem to require a bit more experience and finesse. I know that it’s normal for people to scratch their heads as people they used to think of in short pants growing up to be important and accomplished professionals, but this is somehow different. In the same way that New York businesspeople who spent many years around Donald Trump have been amazed at how the rest of the world can take him seriously as a leader, watching his associates get handed positions of great importance and authority is equally troubling. That is especially the case if you’ve spent time getting to know them in their former capacities.
This story starts as one about how Donald Trump has so altered the expectations of what standards of professional excellence qualify for the highest positions in the land. When history looks back on these days, this will not be simply a case of people with questionable motives and ethical foundations being corrupted by power that has been thrust upon them. This will be about the wholesale lowering of standards and the ignoring of norms that at least tried to establish a bar that people had to get across to be considered for important positions. The two most identifiable standards for acceptability into this administration’s cadre of “best and brightest” would seem to be, first and foremost, blind loyalty to Donald Trump (not his ideals, just the man himself), and the second would be their history of being able to garner wealth for themselves.
When I took over a distressed commercial property developer in late 2008, I did so after a successful 32-year career in banking. I had no significant real estate experience, but the problems the company faced were viewed as banking problems more than real estate problems (though it turned out being a good quantum of both existed). Specifically, the prior head of the operation had been a young and ruthless attorney who managed to not only buy and over-leverage at the peak, but do so with his hand deeply in the till on each and every acquisition. The creativity of the larceny was only exceeded by the amount of frivolity deployed in the process. Executive bad behavior is hardly a rare phenomenon in American business, but none is usually more evident than in real estate development, and especially real estate development in places like Las Vegas and Miami. Las Vegas has long been the sin capital of America and Miami is the tropical dirty money point of entry that amps up real estate partying in that town. It was at the intersection of those things and places that I encountered Steve Witkoff. The company I was tasked to clean up owned more vacant land in Miami than anyone (not to mention the second tallest skyscraper in construction there) AND the largest single development lot in the middle of the Las Vegas Strip, right next to the Hard Rock Cafe Hotel & Casino, complete with its famous pool scene seeded with the most glamorous hookers and strippers of both sexes in town.
At the center of activities in both Las Vegas and Miami, and with a tight and storied history with my conivingly aggressive predecessor, stood Steve Witkoff. I heard more than a few tales of infamous private jet trips between Miami, Las Vegas and New York. By 2008 the hangover from all the real estate partying of 2006 and 2007 was quite sobering and people like me were trying to sort through the rubble to find solutions, but also marveling at the brashness of what had gone on. And there again was Steve Witkoff.
I have no evidence of wrongdoing on his part, but it’s hard not to wonder about people at the center of such a raucous time and such bad business behavior. He was very much still a force in both the Las Vegas project and the Miami market overall (not to mention the NYC condo market that my company was also into), that I had no choice but to try to work with him. I recall one meeting in Miami where he wanted me to partner on some latest greatest waterfront hotel cum rooftop disco in exchange for securing rights to some of our vacant lots. He drove up in his Lamborghini and I drove up in my little white rental PT Cruiser that looked like a funny old milk truck. I beeped my cute little horn to get his attention and he spent the next ten minutes explaining to me why a hip presence was so important in the real estate development game.
And now imagine my quandary that this same man is flying to Oman on some presidential plane like Air Force One to negotiate on behalf of America the nuclear non-proliferation issues with Abbas Araqchi, Iran’s master negotiator. This is, of course, after he spent time in Moscow with Vladimir Putin, negotiating on our behalf for an end to the war in Ukraine. Oh, and let’s not forget that he had already met with Benjamin Netanyahu in Tel Aviv about the Gaza ceasefire. So on our team is Steve Witkoff against Abbas Araqchi, Vladimir Putin and Benjamin Netanyahu. Hmmm… Those are some pretty noteworthy opponents, don’t you think? I feel like America may be driving up in a white PT Cruuser and beeping its horn at these guys. Well, at least we have the success of the Gaza ceasefire and the speed of the Russian peace concessions with Ukraine to inspire us to feel that those Iranian nukes will never see the light of day.
I have only one question for the Universe: How the fuck does this happen?