Convicted Felon Carlos Watson's Wild Ride
On a plane ride to prison the word had come down: instead of a decade in prison and $96 million in forfeiture and restitution Huckster Carlos Watson was free to go. So what gives?
Where did it start? Well, in substack terms it started here with the piquantly titled first (honest) piece I’d done on the fraud Carlos Watson: OZY Rules: The House Negro Gets It in the End.
It predated the New York Times piece I’d written on him by a few days and both did what Ben Smith’s original takedown piece only hinted at. They described the man as only those who worked for him could have: imperious, bilious, abusive and for such a middling talent, baselessly arrogant.
I couldn’t bring myself to tout the man’s obvious virtues as viewed by those above him though. To them he was charming, if a little glib, warm in a Dale Carnegie way, and gifted with an educational pedigree that made them all feel good about flowing him $83 million that they’d never ever see again.
But then there were the marquee moments that soon followed. Killing OZY. Then rebirthing it. Then the chat show circuit where he declared his innocence, despite in the case of Charlamagne tha God having already grifted the man out of a sizable sum. Watson had, in a burst of reinvention become the Super Negro who was being hounded by the white establishment.
It was a Clarence Uncle Tom-esque bit of high-tech lynching, this attempt to mau mau the system into submission. Roland Martin was having none of it though and called bullshit on Watson in the most wonderful way possible. “Where were you and that $83 mil when Black media was struggling to get funding?”
“Today was such a shock to the system…. The idea that one of the most reprehensible people I’ve ever met was so obviously guilty, was convicted and got off absolutely scot-free has shaken me.”
Watson, for his part, did what he had always done. Equivocate around Martin’s turn to position it as a minor misunderstanding between fellow travelers. Except for one thing: Roland Martin would not be arrested the way Watson would eventually be.
Then, with real skin in the game, a certain seriousness was now demanded. At least from my point of view as I bounced on a balance ball at jiu jitsu and chopped it up with two FBI agents asking about Watson. I’m not a snitch, and now that we have gotten that established know this: I told them everything I knew about the man. The 30 minute interview stretched into two hours, which is about how long it took me to exhaust my bile.
You see, they say the opposite of love is not hate but indifference, and there the reality stood. I’m incapable of being indifferent about a clubhouse cancer like Watson. I’ve seen him do things to the people who worked for him that I’ve never seen any CEO do and I’ve worked with some of the best. Andy Grove, Steve Jobs, among them, were tough and mercurial, but most of all they were effective.
Watson? Not so much.
Arrested, then on trial, it was all laid bare. The magical bookkeeping, the deluge of lies, well beyond the usual Silicon Valley puffery, the identity theft, the fabulism that kept the money pouring into our mission critical efforts to, in the end, make him “famous.”
As it all played out, even worse (or better, depending on your vantage point), his scattershot defense and flouting of legal protocol, contempt for the proceedings and goading of the judge and prosecuting attorneys was a study in how not to run a defense. Sanctioned by the judge on a number of occasions when the verdict finally came down, the scene caused by his family in court backlit a textbook example of people who were sick of Carlos’ shit, he was remanded into custody for his only real taste of…reality.
After about a month in the detention center in Brooklyn, a shaken Watson appeared in court to petition for a move to solitary/protective custody. His attorneys weren’t saying that he hadn’t been sexually assaulted. But they were adamant: he was in fear for his life and he had “problems”.
Problems of the kind you might have in the stony lonesome, Watson would get the only real reckoning of the whole schmeer, and duly chastened he was finally released into the brave, new world where he might have really understood that actions have consequences.
But where others would start playing contrition, Watson zagged and attacked once out and under “house arrest”. The judge was biased, had conflicts of interest, playing the stock market “like a dreidel” (in a burst of curious antisemitism), their defense was hobbled, the sun was in his eyes and a whole specific line of excuses framed by his original high tech lynching bit.
At its most risible high point, one of his lawyers compared him to Martin Luther King. My most hardcore desire at this point was to see them stretch the comparison to include Jesus Christ. I would have even accepted the use of the word “crucifixion” for the Daily Double of ridiculousness, but this was not to be.
He was sentenced, curiously, to the same amount of time I worked for him, nine years and eight months, and then in short order $96 million in fines.
“[I]f he does not believe that he did anything wrong it is likely he will repeat all of that. But who is actually going to trust him now?”
And the world at this point? Looked just fine to me. The good were making right this evil wrong and Watson, now remanded to house arrest, had been contacted by my producers on the upcoming OZY series.
“Would you be willing to be interviewed by Eugene Robinson?” They had cornered him outside of the court room.
“No!” Then after a few beats. “Not at the present time.”
I had largely, my dislike of the man slaked, started paying attention to other things. All through the Trump chatter and before that the Biden chatter that Watson would be forgiven all of his many and varied transgressions.
Chatter that didn’t hold much water for me. Right up until it did.
Because in a burst of outside of the box thinking Trump did indeed commute Watson’s sentence. The rumor mill swirled. Was it to “own” early investor and ardent lefty billionaire Lauren Powell Jobs? Was it at the behest of Ivanka Trump who imagined that this was a way to win over “The Blacks”?
It didn’t matter. The man who had been headed, according to reports, to Lompoc Prison, was now at home, no longer under house arrest, doing a victory lap in a place where convicted felons don’t have to go to prison just, well…because.
When asked if he would reoffend one of OZY’s former board members opined “Well, he definitely does not feel any guilt or shame. So if he does not believe that he did anything wrong it is likely he will repeat all of that. But who is actually going to trust him now? A job in the Trump Administration? Can you imagine?”
Down the line the rank and file response was a skosh more bellicose. Former employees, even the ones that thought he had been punished enough, were outraged. And disgusted. The hurt he had caused them would not be soon forgotten and possibly never forgiven. Even more so now.
“Today was such a shock to the system,” one said under a request for anonymity because, yeah, we’re back to fear again. “The idea that one of the most reprehensible people I’ve ever met was so obviously guilty, was convicted and got off absolutely scot-free has shaken me.” And she was from the demographic that’s had a tendency to be most supportive of Watson, older women of color.
“And beyond Carlos, the way that Trump is normalizing criminal behavior to make himself seem less criminal is…disheartening.”
But I’m a lifelong athlete and unlike Trump and others of that ilk I can take the L. In the end as one of my MAGA friends suggests, none of this has anything to do with me. Even in the face of us living in a country of laws and standards that, if ignored, seem to undercut the very fabric of how we — the judge, the 12 jurors, and everyone who lost money to the huckster Watson — understand right and wrong.
“You didn’t lose anything after all,” she said. “And you gained peace of mind.”
“He grifted $35,000 out of me,” I said. “That’s a loss. Of cash and peace of mind.” She shrugged but finally the best and most trenchant take came from Kevin Merida, former executive editor at the Los Angeles Times.
“What’s going to happen when you see him again?” Merida asked, breathlessly and for all the world taking me back to junior high school. Like there was going to be a fight after school got out.
“I’m a firm believer in doing what Sinatra said,” I said. “Keeping the party polite. Even more so if I get my $35,000 back.” But that’s never going to happen (for the record Vice also owes me money for my chapter in the Vice Guide to Sex, Drugs and Rock and Roll, and they’ll never pay either).
So the convicted felon Watson beats the rap, is back on the grift and making Elisabeth Holmes and Sam Bankman-Fried wonder where they can get in on some of that high tech lynching stuff.
For my part? It’s become pretty clear to me that whatever price had to be paid to Trump, transactional as he is, was probably worth it to Watson since paying off your debt with ass, grass or cash means very different things outside of prison than it does inside.
Also, the morning line opens with Watson a clear fav to reoffend, with the over/under putting us at before 2025 is done. So is it true that the House Negro gets in the end? Only time will tell. Until then realize this: crime is no longer illegal in America…so have at it y’all!!!
And tell them Donnie sent you!
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I can't even, bro. This, this is something else right here. Fuck, these people suck. Thanks for the reporting, Eugene. The Showstomper is going to be Lit, today.
Another Shithole country merit badge for America with Watson’s release.