Why would Donald Trump commute Carlos Watson’s fraud sentence?

Why on earth would Donald Trump commute the fraud sentence of OZY Media’s Carlos Watson? I ask the question in some astonishment considering that Mr Watson was convicted by a federal jury and sentenced to nearly 10 years in prison for trying to defraud investors and lenders by lying about the company’s finances as well as identity theft.

What possible reason would the US president have for commuting the sentence of a co-founder of a now-defunct digital media company?

Why have Mr Watson and OZY received the presidential benediction of no longer having to pay $96 million in financial penalties for the actions for which he was convicted?

Mr Watson had pleaded not guilty and continued to assert his innocence up until he was sentenced. He has insisted that the charges were racially motivated.

Even so, if we are to believe in rule of law, justice, and crime and punishment, surely we must respect the jury’s verdict and the judge’s sentence?

Not in Trump’s America, it seems.

Indeed, when Semafor’s Max Tani asked In Retrospect podcast host Susie Banikarim if she was surprised by Mr Trump’s commutation of Mr Watson’s fraud sentence, she said she wasn’t.

“Not entirely surprised,” were her exact words. And the reasons she offered are revealing. Ms Banikarim said: “Watson has said some nice things about Trump recently”.

She added: “…in many ways, Carlos is a Trumpian figure – someone who seems to always find a way to make the system work in his favor”.

So what’s all this about? Will Mr Watson serve the Trumpverse? And if so, how?

It is possible that the answers to these questions may lie in Mr Watson’s arguments during his prosecution and now, after the presidential commutation.

As The Guardian has reported, in his statement after Mr Trump commuted his sentence, Mr Watson alluded to some of his defunct company’s successes. One of these was the Emmy-winning Black Women OWN the Conversation, which he hosted and which appeared on the Oprah Winfrey Network. He said that jealous competitors orchestrated what Mr Watson characterized as a “malicious” prosecution. And he added: “We are ready to move forward, guided by the lessons I learned.”

What lessons learned would he apply to a new Trump landscape? One in which Mr Trump started his second term by issuing a handful of commutations and a blanket pardon that effectively freed all the January 6, 2021 rioters and erased the work of the largest criminal investigation in US history.

Mr Watson could be useful to Mr Trump in some ways. For example, he could say how fair and impartial Mr Trump is to a black business owner and that he is living proof of that.

After all, Mr Watson didn’t receive a pardon but a commutation. Most commutations come with conditions and if they are violated the convict could be sent back to prison. We don’t know the conditions of Mr Watson’s commutation.

In any case, it would be in Mr Watson’s interest to be persuasive about Mr Trump’s qualities as a just and fair person irrespective of their race.

There is little doubt he will be persuasive. Mr Watson is excellent on radio and TV and his personality is charming in all sorts of ways.

In fact, when I read that Mr Trump had commuted his sentence, my mind went back to my meeting with Mr Watson 11 years ago in Mountain View, California.

At the time, Mr Watson was the fresh-faced founder of OZY, relentlessly looking to find and feature what he repeatedly described as “the new and the next”. He told me how keen he was for OZY to lead conversations about subjects less covered or not even thought about. Both Mr Watson and OZY co-founder Samir Rao took great pride in telling me how they named their company after Shelley’s poem Ozymandias, which explores the transience of power and inevitability of decline. They came across as insightful, almost wise in their unusual acceptance of impermanence despite founding a Silicon Valley media startup.

In our conversation, Mr Watson and Mr Rao seemed genuinely excited about the future and I was equally excited at the thought of possibly  working with them.

That didn’t happen for various reasons, not least my family circumstances though I wrote for OZY a few times.

After this, I rather lost sight of Mr Watson and his media outlet. And then, one day, it was all over the papers that Mr Watson and Mr Rao had been accused of various offences.

Mr Rao, incidentally, pleaded guilty in 2023 to fraud charges and testified against Mr Watson.