Tommy Bennett, 56, has one of the most positive outlooks on life you’ll ever encounter. In a soft but firm voice, he speaks about his love of people and his belief that he got where he is now “by God’s grace.” He is known in the homeless community for giving advice and support, as well as making new friends easily.

Bennett, who has been selling Street Sense for nine years, has not always been as calm or optimistic as he is now. Born in Tennessee, his family moved to Southeast Washington, D.C., when he was three. After graduating from Anacostia High School, where he played football as a wide receiver, Bennett worked a few jobs and then enrolled in the Navy, where he participated in seek and destroy missions.

Bennett says he started “getting in trouble” after the Navy, but worked for Mayflower as a mover for several years.

“I was Mover of the Year three times in a row, and I got a plaque,” Bennett said, adding he was about 35 years old at the time. Soon after, Bennett injured his knee and had to stop working for Mayflower.

“I said, ‘Dang, my whole life is ruined,’” Bennett remembered. “[Then] I hooked up with some so-called friends of mine and got into the dark world,” what he calls selling drugs.

Bennett was arrested several times and always released on probation, but finally a judge sentenced him to a year in prison.

He was let out early with his record wiped clean. After his stint in jail Bennett stayed clean for 20 years, but he eventually turned back to the dark world.

“My record was clean, [but] I started hustling again,” said Bennett. “I didn’t need to hustle. I had a nice apartment, everything I wanted, but I got bored.”

When arrested again, Bennett was referred to an outpatient program where he says the head of the program “told me she [saw] something in me.”

The program also introduced him to Jose, one of the original Street Sense volunteers, who offered Bennett a chance to sell newspapers. At first, he struggled.

“I got frustrated,” Bennett said. “I said, ‘Jose, people don’t buy this paper!’ Then Jose gave me the key. He said, sell yourself with the paper… I went back and thought on that slogan.”

The next day, Bennett said, “Street Sense this morning for the homeless, and have a nice day.” He made his first sale soon after, and has been selling papers ever since.
Bennett lived at Franklin Shelter until it was shut down, then moved to 801 East Men’s Shelter. At 801, he became known as an informal counselor who helped others find ways to leave the shelter.

“[The counselors] don’t tell people the right sources to get out,” he said. “What I was doing was telling them the right sources.”

Bennett also became somewhat of a local celebrity when he wrote an article exposing some of 801’s shortcomings. He appeared on the news and says the shelter staff made some positive changes to the living conditions afterward.

“They started painting the bathrooms and trying to fix them up,” he explained. “[The manager] said, ‘Why are you messing with my staff like that? You make us look bad.’ I said, ‘I’m telling the truth, it is filthy! You wouldn’t live in here like this, would you?’ He looked at me and didn’t say anything.”

Then one day Veterans’ Affairs came knocking. Bennett had filled out the correct forms to receive housing through the agency, but he was still waiting after a year and three months.
“I went to the guy who runs the housing for vets [department] and I talked to him … I said, ‘Your assistant told me I would get my apartment in six months to a year. It’s been a year and three months. Are you all gonna give me an apartment, or are you just messing with me?’”

The man told Bennett he would receive his apartment in two weeks’ time, but “I thought he was pulling my leg,” he said.

But Bennett got a phone call two weeks later telling him to pick up the keys to his new apartment.

“I didn’t believe it,” he said. “It was like a dream. I had to get used to the apartment [because] I was brainwashed since I was in the shelter.”

After two and a half years, Bennett has happily adjusted to life in his apartment. As he wrote in Street Sense recently, he has also been clean for 10 years and feels comfortable with his place in life.

“Where I’m at now, I’m at peace with myself,” he says.