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Homeless Yale grad living on streets of Los Angeles gets help from fellow alum

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Prestigious degrees and high-paying jobs did little to stave off the demons that left Shawn Pleasants homeless and living under a tarp in Los Angeles.

The valedictorian of his high school in San Antonio, Texas, Pleasants was accepted to Harvard, but chose Yale, where he majored in economics. Banking jobs on Wall Street followed. Later, he moved to California to be his own boss.

He launched a film-making and photography company, which in the 1990s, became involved in the adult film industry and made him enough money to buy a fancy home in Silver Lake.

But the money dried up, and when his mother, a teacher, died of cancer about a decade ago, he went into a tailspin. Depression and addiction followed.

September marked the 52-year-old’s 10-year anniversary on the streets, and his plight received media coverage when Trump administration officials visited the city to survey its homelessness crisis.

Kim Hershman, who’d studied a year ahead of Pleasants at Yale, saw his story on CNN, and though she knew him only in passing in their Ivy League days, she felt obligated to help. His Koreatown encampment was just a few miles from her home.

Sean Pleasants at his Los Angeles homeless encampment.
Sean Pleasants at his Los Angeles encampment.CNN

“When we were at Yale in the ’80s, there were very few black students there,” Hershman told CNN. “Things are very different now. But I know that for whatever he achieved, something changed, and he didn’t have the support that, maybe, I had.”

Hershman, who also graduated from Yale Law School and works as a Hollywood business consultant, tapped into her alumni network, and after a flood of posts offering help appeared on a Facebook page for black Yale alumni, she went searching for Pleasants.

When she found him, she asked him what he wanted.

He told her.

“I want to make a difference. I’m in this situation, and there has to be a reason for it all, and I want to help others.” He had a dream to create a resource center for the homeless, where people living on the streets could take showers, receive mail, charge a phone or clean their clothes.

Hershman said she’d try to help, on the condition that he agreed to go to drug rehab. After all, he turned down similar offers before.

But this time, he said “yes.”

A week later she returned to check on him, with a trove of messages of support from their Yale classmates. “The messages are really what made Shawn decide to move off the street.”

Hershman found a guest house at an LA estate for Pleasants and his partner, David, who lived with him since before they became homeless. It took him weeks to acclimate. “At some point, someone is going to say, ‘April Fools,’ and it’s over,” he said.

On Friday, he checked into rehab.

He’s written a note for the next edition of Yale’s alumni magazine that reads, in part, “I need more than a helping hand. I need a map as to where I’m going. Thank you for providing that – at a level that ‘another Yalie’ appreciates.”

With Hershman, they are working on a way to make his vision for a resource center a reality.

Pleasants knows some are wondering if he’ll blow it and wind up back on the streets. “I hope the hell not,” he said.

“And I hope for their sake that they don’t lose their footing, because they’ll experience some of the worst times that I experienced. And it doesn’t matter who you are, it’s a possibility.”

Kim Hershman with Shawn Pleasants the day he entered rehab.
Kim Hershman with Shawn Pleasants the day he entered rehab.Kim Hershman

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