A titan: From homeless to helping hundreds

Charles Sheppard’s family spent years wondering what happened to their brother. They hadn’t heard from him in years and thought he was living on the street, hooked on drugs. They weren’t wrong.

But by the time they found him, he was already turning his life around. He came to the Milwaukee VA to get clean and find housing, receive training and find a job. That may have saved his life, but family, friends and co-workers said he paid it forward hundreds of times over.

Sheppard, 61, a peer support specialist in the Milwaukee VA’s homeless outreach program, died June 8 after a three-month battle with COVID-19. He was remembered as helping hundreds of Veterans kick drugs and alcohol and finding them a permanent place to live.

Always caring and respectful

“He had a heart that was boundless and he was always so caring and very respectful of everyone, no matter who they were,” said Barbara Gilbert, Milwaukee VA’s Homeless Veterans Program manager. “When it came to helping a Veteran, he left absolutely no stone unturned.

“Charles found Vets wherever they needed to be found. He went to the ends of the earth to make sure he got them housed. He lived these experiences, and he was successful because he could connect with people living in that experience.”

Sheppard is pictured above (standing on the left) with members of the Milwaukee VA homeless outreach team.

“None of them could sing a lick.”

Sheppard came from a big family with an older brother and seven sisters. The family grew up close, hanging with friends and each other on a big porch.

“I remember his friends wanted to start a band like Gladys Knight and the Pips. They were going to be their own boy band,” his sister Valery recalled. “But none of them could sing a lick or keep in step. But they kept singing.”

Valery joined the Army a couple years later. “He always said he was better because he was Navy and I was Army,” she laughed. “He spent all his time on a boat and I got to live in Germany, in a nice little town. We were always talking about our time in the military after he got out.”

Then he was gone.

His sisters aren’t sure when or how it exactly happened. But they missed him and wondered what happened to their brother who always sang off-key, had a smile on his face and never stopped talking.

When Sheppard found his way to the Milwaukee VA, he had no idea how hard they were looking.

“He was just an amazing light.”

After his initial treatment, he was given the chance to get training through VA’s Compensated Work Therapy program, which provides structure and teaches life skills while providing a job and responsibility.

“Charles was a hot mess. He was a handful when I first met him in 2008,” said Ann-Marie Nelson, Vocational Rehabilitation Program manager. “He was new to treatment and he struggled to accept supervision.”

He moved into a full-time job as a Milwaukee VA housekeeper before the peer support opportunity opened. The intent of the peer support program is to hire Veterans who have been through treatment successfully, so they could help others.

Dr. Erin Williams, a Milwaukee VA psychologist, said the hospital was expanding the program and there were a lot of applicants. She was on the interview panel.

“He was just an amazing light. We interviewed so many people. His scores were the highest. He was off the charts with his emotional intelligence. Maybe he didn’t have all the education, maybe he hadn’t been given the opportunities, but he had an insatiable curiosity. He hungered for knowledge.

“You’ll hear his laughter echoing with pure delight.”

“His mom died while he was young. A lot of people get bitter and hardened and, for whatever reason, he did not. Charles was the most amazing person, and stubborn in a good way. He had a drive.

“He was such an inspiration. Look at all this stuff he accomplished in 12 years. He went out with a bang. I think it is miraculous. The stuff he did in 12 years is what takes some people decades. For some, it takes a lifetime to do what he did.”

While co-workers grieve, they’ve been sharing their stories and feelings. Williams sent this text to her friend after learning of Sheppard’s death:

“My heart is absolutely broken though I’m sure he’s enjoying heaven. If you listen carefully, you’ll hear his laughter echoing with pure delight. You know he’s asking lots of questions. And he’s never known a stranger so that place will never be the same.”

Here is the full story of Charles Sheppard’s life.