He was a Yale graduate, Wall Street banker and entrepreneur. Today he’s homeless in Los Angeles

Updated 8:53 PM EDT, Tue September 17, 2019
Courtesy of Michael Pleasants
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(CNN) —  

Shawn Pleasants has the kind of resume that would attract the attention of any job recruiter: high school valedictorian, economics major from Yale University, Wall Street banking jobs, small business entrepreneur. But a few wrong turns in life 10 years ago left him homeless, and today he’s living underneath a tarp in the Koreatown section of Los Angeles.

He’s been told before that a smart and capable person like him should not be in this situation.

“But I’m like, should anybody be here? Who should, then?” Pleasants said.

Last week, Trump administration officials came to Los Angeles to examine the homelessness crisis. The President, who clashes with California politicians on a number of issues, has made frequent reference to the state’s failure to solve the problem.

Shawn Pleasants' Yale yearbook photo.
From Yale University yearbook via Michael Pleasants
Shawn Pleasants' Yale yearbook photo.

Trump is visiting the West Coast this week, amid reports that his administration is about to launch a crackdown on homelessness – potentially involving dismantling encampments and moving the homeless en masse into a government facility, according to the Washington Post. (It’s not clear how this would work or whether the President has the authority to order this kind of action.)

Against that backdrop, Pleasants’ story is a reminder of how complex the problem of homelessness can be. “It means it can happen to anybody. It’s a problem we all could face,” Pleasants said, standing on a sidewalk in front of his weathered belongings. A couple of unopened cereal boxes that he just collected from a food pantry sit atop his things.

Shawn Pleasants now.
Shawn Pleasants now.

“I am responsible for my own choices. I own all my decisions,” he said plainly before telling his story.

Pleasants, 52, is one of 60,000 people living on the streets of Los Angeles County. The situation has been worsening in recent years – between 2018 and 2019, the number of homeless people went up 12% in the county and 16% in the city, according to the Greater Los Angeles Homeless Count. Along LA’s skid row downtown, tents line entire blocks, and encampments in other neighborhoods have been growing.

Mike Dickerson, an organizer for the homeless advocacy group Ktown for All, says the stories of many people living on the streets might surprise you.

“I think a lot of people have this perception that danger lurks in the encampments,” he said. “And for myself and for other volunteers, what we found is people who are just people like everyone else, who have fallen into hard times, whether that’s because of their own personal issues of because their landlord evicted them or because the rent rose in a way they could no longer pay.”

One man’s journey into homelessness

Pleasants grew up in San Antonio, Texas, the product of a stable, loving family who always excelled in school, according to his younger brother, Michael.

Their mother was a teacher, while their father made a career in the Air Force.

“He was always as a young child taking things apart and putting them back together,” said Michael Pleasants, who followed his brother’s footsteps to Yale. “He was a whiz kid.”

“He (Shawn) played trombone and won several civic awards around the city.”

Shawn Pleasants in first grade.
Courtesy of Michael Pleasants
Shawn Pleasants in first grade.

Pleasants also overcame a physical disability. He was born with a club foot and wore leg braces throughout his childhood, his brother said. His doctor joked he would never run a marathon. In fact, his brother said, he’s run several, and was in peak physical condition through his 20s.

Pleasants was a high school valedictorian, who had offers from multiple colleges, according to his brother.

Shawn chose Yale and said he received grants and several academic scholarships, which covered most of his tuition. CNN has verified that he graduated from the university.

Shawn Pleasants at his Yale graduation with his mom, Gloria.
Courtesy of Michael Pleasants
Shawn Pleasants at his Yale graduation with his mom, Gloria.

He majored in economics, and after a few years toiling on Wall Street, including jobs at Morgan Stanley, he landed in California. Trying to fulfill a Hollywood dream, he started a photography and filmmaking company.

It was the mid-’90s, and as the DVD industry soon exploded, his company got involved in the then-lucrative world of the adult film industry. They made so much money that Pleasants wound up buying a large home in the Silver Lake neighborhood of Los Angeles.

“It was a beautiful house, something you’d see on MTV,” said his brother.