The rise and fall of Shawn Pleasants, Yale graduate and Wall Street banker who lived large but now homeless

Michael Eli Dokosi September 19, 2019
Shawn Pleasants. Photo credit:

Shawn Pleasants, a homeless man on the streets of Los Angeles County, U.S., is not your average man and though he finds himself in a tough spot, he’s refused an offer to move in with his 86-year-old father in San Antonio.

Here is a high school valedictorian who majored in economics at the Yale University, worked at notable banking and investment companies, including Morgan Stanley on Wall Street, as well as, owned a business.

Having left Wall Street, Pleasants’ company ventured into the lucrative adult DVD film industry of the mid-’90s. With good money pouring in, Pleasants acquired a large home in the Silver Lake neighbourhood of Los Angeles.

However, as with most business partners, squabbles among the co-founders stalled the progress of the business and aided in its eventual collapse, a report on the life of Pleasants by the CNN said.

When Pleasants’ mother died around the same time due to cancer, he was devastated. With no money, he started leaving from place to place, eventually living in his car, which, unfortunately, got lost.

The rise and fall of Shawn Pleasants, Yale graduate and Wall Street banker who lived large but now homeless
Mr. Pleasants with mum via

The gay man, who has his gay partner with him on same Koreatown sidewalks for six years, is aware U.S. President Donald Trump is visiting the West Coast this week, amid reports that his administration is about to dismantle encampments to move the homeless en masse into a government facility.

Pleasants, who has been homeless for 10 years, says practical measures such as offering bathing facilities is critical to stopping the outbreak of diseases among the homeless.

“We need places to shower, if you don’t want us to have hygiene issues, and in order to get a job, we need to have clean clothes. Where do I iron? How do I keep them pressed?” he said.

Pleasant’s determination to bounce back to good fortunes and not be a burden on anyone, including his family, is commendable.

He noted: “I am not trying to bring another family member down. I fell into it. I have to climb my way out of it,” adding “I’m gonna start a small business again.”

When told that as one who graduated from an Ivy League school, owned a house and made a nice living, he shouldn’t be in his predicament, 52-year-old Pleasants queried.

“But I’m like, should anybody be here? Who should, then?” adding “I am responsible for my own choices. I own all my decisions.”

America’s homelessness is a source of concern for many observers. 60,000 people are estimated to be living on the streets of Los Angeles County with the number of homeless people shooting up 12% in the county and 16% in the city, according to the Greater Los Angeles Homeless Count.

Pleasants grew up in San Antonio, Texas, born to a mother who was a teacher and a father who served in the Air Force.

He’s always shown his brilliance and according to his younger brother, Michael, Pleasants played the trombone and won several civic awards around the city.

Despite being born with a club foot requiring he wore leg braces throughout his childhood, he soon walked well and won several marathons in his 20s.

His brilliance and being a high school valedictorian meant multiple colleges desired him. When he chose Yale, Michael notes that he received grants and several academic scholarships, which covered most of his tuition.

Not a fan of a restricted place or shelter that the government wants to send them into, Pleasants believes a shelter would restrict his freedom and is concerned he wouldn’t be able to keep all of his things due to a lack of space.

Perhaps a back injury he sustained even before he became homeless might have added to his drug use and addiction as well.

“It started with pain killers, and then when they were too expensive or not accessible he medicated with other things,” Michael said.

Pleasants himself stated he takes meth a few times a week as both an escape and to help him stay awake at night.

Pleasants hasn’t lost his knack for knowledge as he owns both a laptop and a cell phone. The phone and its service are free under an Obama-era program. He spends a lot of time at the library, accessing the internet and staying on top of current events.

Deploying his intelligence to stand him in good stead, Pleasants has studied the schedule of where and when to get free meals efficiently until he breaks through once again with his new business module.

“There’s certain churches (that provide meals), certain food pantries — you learn those schedules,” he explained.

Last Edited by:Mildred Europa Taylor Updated: September 19, 2019


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