A titan: From homeless to helping hundreds - Milwaukee VA Medical Center
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Milwaukee VA Medical Center


A titan: From homeless to helping hundreds

Charles Sheppard and the homeless outreach team

Charles Sheppard (second from left) and members of the Milwaukee VA homeless outreach team.

By Gary J. Kunich
Tuesday, June 23, 2020

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.

By the time they found him, he was already turning his life around. He came to the Milwaukee VA to get clean, get housing, training and 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 15 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.

“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, Homeless Veterans program manager. “When it came to helping a Veteran, he left absolutely no stone unturned.

“He found Vets wherever they needed to be found. He went to the ends of the Earth to make sure he got them housed.” Barbara Gilbert, talking about how hard Charles Sheppard worked to help his fellow Veterans.

“He 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.”

Tiffany Phelps, a Milwaukee VA employee in Spinal Cord Injury, called him “miraculous.”

She was working in the Milwaukee VA library in 2008 when Sheppard was first going through treatment at the domiciliary. He would come to the library to use the computers.

Phelps was going through a bad time herself – her marriage ended, and her sister had died. She was a single mom raising her 3-year-old daughter and now a 13-year-old niece.

“At first I didn’t really like him. He grew on me,” she said. “At that point in my life, I didn’t like anybody. He was always talking. Then one day he came in, and he cracked me. He said something that made me laugh. That’s the way he was. He wasn’t going to give up.”

They became friends even though he relapsed.

“I gave him tough love,” she said. “I told him to get his (stuff) together.”

“I’m going to come back and I’m going to make you proud,” he told her. “I’ll show you.”

The next time she saw him, he was on his feet. He entered Milwaukee’s Compensated Work Therapy program, which provided a job and some structure.

Charles Sheppard from his Navy days.


Meanwhile, his sisters were trying to find him, spending years scouring phone books, calling crisis centers and driving through different neighborhoods.

“We knew he was on the street and lost track of him,” Valery Sheppard said.

Charlene Adkins, his oldest sister, said they finally connected the dots online.

“We knew we could find him with God’s intervention. We searched the web, we found a counselor, then we found his sponsor, and we called the sponsor.”

The sponsor told the sisters he had seen Charles a few weeks earlier.

“Please tell him we’re looking for him,” she told the sponsor.

“And on Veterans Day, he called us,” said his sister, Rose, “and me and him, we just cried. We knew it was God. Because he’s a Veteran and he called us on Veterans Day, and we had our brother back.”

Charles Sheppard

Charles Sheppard shared this photo of his college graduation with friends and coworkers. He was going back to school for his bachelor's and had plans to become a social worker.

The family reconnected, spending holidays and family dinners together. Phelps said her friend was a changed man.

“We’d see each other at least once a week and just talk,” she said. “He was always checking in, telling me about his life and how he was doing.”

She told him about the peer support specialist job with the homeless program and helped him fill out the application.

“We worked on it for two days, and he got the interview and got the job. He came here with no money, and he bought a house, bought a car and was making great pay.

“And now that I look back and think about it, I thought I was the one giving him encouragement. I think he helped me.” Tiffany Phelps, talking about her friend, Charles Sheppard.

“And now that I look back and think about it, I thought I was the one giving him encouragement,” Phelps said. “I think he helped me, when I was going through a real (bad) time. He helped me get through all that. He helped me, too.”


Charles Sheppard came from a big family with an older brother, Robert, 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, based off Gladys Knight and the Pips. They were going to be their own boy band,” Valery said. “But none of them could sing a lick or keep in step. But they kept singing.”

Robert joined the Navy, but in 1966, he drowned under mysterious circumstances in the Atlantic Ocean while stationed in Rhode Island.

“That’s why Charles joined the Navy. He wanted to find out what happened to our brother,” Charlene said.

Valery joined the Army a couple years later.

“He always said he was better because he was Navy and I was Army,” Valery 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.

After his initial treatment, he was given the chance to get training through CWT, which provides structure and teaches life skills, while providing a job and responsibility.

“He was a hot mess. He was a handful when I first met him,” in 2008, said Ann-Marie Nelson, the vocational rehabilitation program manager. “He was new to treatment, and he struggled to accept supervision.”

Sheppard was back in the program for a second try in 2010.

“The Charles Sheppard who came back was much different,” she said. “He rose above. He had personality. He had this flair, his smile, his sense of humor and his laughter.”

He moved into a full-time, regular 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,” she said.

“We interviewed so many people. His scores were the highest. He was off the charts with his emotional intelligence,” Williams said. “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.”

“I wish we could do like those sci-fi movies and they could transplant your brain into my head,” he told her once.

“If he wasn’t doing something the absolute best, he wanted you to tell him,” Williams said. “He always wanted to learn more. He helped the other peer specialists do their jobs.”

These two people from totally different worlds became fast friends.

Charles Sheppard

Charles Sheppard and his son, Isaiah, pose with a realtor after he closed on his second rental property.

“His mom died while he was young. A lot of people get bitter and hardened, and for whatever reason, he did not. He was the most amazing person and stubborn in a good way. He had a drive,” she said. “We were really, really, really close, and he would stop by my office to talk all the time.”

Nelson ran into him again at a peer support conference in San Antonio in 2019.

“It really hit me how much he had changed over the years. He was so different at this conference, so professional. I remembered way back when, and he was a completely different human being. You could see the whole transition.

Charles Sheppard and his friend and coworker, Dorothy McCollum, a homeless prevention social worker, at a 12-step recovery outting. Charles was remembered as always having a big smile on his face.

“Sometimes it takes a couple tries. And that’s recovery, in general,” Nelson added. “To really see him in his recovery from the beginning, from 2008 to 2019 … what he does for fellow Veterans, and his ability to demonstrate what each Veteran can do, he did remarkable.

“This is why we’re here,” Nelson said. “Then he joined that movement. He lived it.”

Sheppard graduated in December with an associate’s in human services and was going back for his bachelor’s.

“His goal was to be a social worker, and he would have been really good,” Williams said.

One thing missing in his life was the chance to be a father. He had a child, Isaiah, at age 58.

“He always wanted to be a dad. He just adored this kid,” Phelps said.

Isaiah was the “absolute love of his life!” Williams said. “He always dreamt of having a relationship with him like the ‘Courtship of Eddie’s Father,’ he’d say.”

He was also becoming a businessman. He saved his money and bought a rental property. He just closed on a second property in March, days before he got sick.

Isaiah’s mom, Ellamae Gonzalez, said Sheppard called every week from the hospital and couldn’t wait to see his son again.

“He would get better and then get sick again. He’d call and want to talk, but had a hard time breathing. I’d tell him, ‘Call back when you can breathe better.’

“Isaiah keeps calling and looking for his daddy. I don’t know what I’m going to tell him.”

Phelps said she had a dream the night before he died. She was talking to Sheppard, and he told her he was rich. She learned he died the next day, and believes the dream was a sign.

“He was such an inspiration,” she said. “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.”

VA chaplains will soon honor Sheppard and all employees nationwide who have died from the coronavirus.

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 that he’s asking lots of questions ... and he’s never known a stranger, so that place will NEVER be the same."


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