Monday is Trump’s Day of Reckoning

Andy Ostroy
3 min readMar 23, 2024

This coming Monday Donald Trump will have to come up with an appeal bond of nearly half a billion dollars or face New York’s Attorney General Letitia James freezing and seizing his assets to pay his judgement in the state’s civil fraud case.

I’ve been going back in forth in my head with a critical question: would I rather see Donald Trump broke or wearing an orange jumpsuit.

Now don’t get me wrong. I cannot stand this despicably corrupt treasonous sociopath, and would love to see his maggot-infested soul rot in prison for the rest of his miserable life.

But there’s a huge part of me that believes the worse punishment for him is to fuck with his money. To freeze and seize his assets, sell his properties, and shatter once and for all the myth that he’s a wealthy, successful billionaire businessman.

Trump’s entire identity, his entire self-worth, his brand…every fucking thing about him…revolves around that myth. And the stakes are even higher for him now politically as he desperately seeks another shot at the Oval Office. Not because he’s a patriot who loves his country and wants to selflessly serve it, but rather because it’s his only safe haven. Because if he wins in November, he will destroy the Depart of Justice’s independence, shut down his federal criminal trials, and weaponize DOJ against his enemies.

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Andy Ostroy

Director, producer, podcaster, writer, resistor, non-profit-supporter of women filmmakers