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Billionaire Goes Undercover as Homeless Person to Prove You Can Still Be a Weird Asshole Even With No Assets

NEW YORK — Local billionaire Morgan Theodore has confirmed he has undertaken a “poverty challenge” to prove that his inherited wealth, familial connections, and cloistered upbringing have nothing to do with the entitled way he turned out.

“People think the rich are weird assholes because of our money, but that just isn’t true,” says Theodore, who is three days into an experience he says may last as long as an entire week. “I was just as rude to waiters when I had nothing but my father’s checkbook and a dream of buying up all the affordable housing I could find. To prove it, I’ve sold my home, put most of my art in storage, and started over with nothing but a backpack, twenty dollars, and a vague idea of how to reach my pied-à-terre via public transportation.” 

The Theodore Family Trust issued the following statement in response to questions about their scion’s efforts.

“We are proud of Morgan, and fully support him in this brave effort to expose the class warfare currently tearing our country apart. For too long those with means have been depicted as deranged sociopaths, gleefully prodding our country towards fascism and ecological ruin to benefit our bottom lines. As Morgan’s experiment demonstrates, that is simply not the case. We are weird assholes because of who we are on the inside, not what our bank account says. We simply ask to be judged by the lack of content of our character,” The Theodore’s butler Geoffery stated to the press as the family relaxed in the pool.

Anson Leonard, an unhoused father of three who got to know Theodore while helping him figure out which side of the subway platform to stand on, said he came to suspect his friend led a more privileged life than he let on. 

“He tried to hide it, but I could tell. He didn’t understand why I couldn’t just get a loan and buy a house, or all the paperwork I have to jump through just to get my medication sorted out with the VA. Trying to juggle all of it just to get the basics. I need ID to get ID, you know? That kinda bull,” said Leonard. “Though I do admit, if you ask anybody around here, the guy has been a real asshole to practically everyone since he first started coming around. He tried to call the cops on me for taking a nap. They arrested both of us. So I guess he’s proved something, I don’t know what.”

At press time, Theodore says he plans on writing a book about his experiences and has already secured a publishing deal with Theodore Books Ltd. 


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