Cleveland Simmons is someone who has always liked to steer his own ship. It’s because of that he was able to start rehabilitation programmes for prisoners and advocate (loudly) for the downtrodden.

It also led him into trouble with the law — on more than one occasion.

He spent six years in prison for possession of cocaine and intent to supply before being released in 1991.

He came out of prison an addict.

“There were more drugs in prison than on the outside,” the 75-year-old said. “You name the drug and I tried it.”

He thought he was a “functioning” addict until 2001 when he was arrested again, this time for possession of drug paraphernalia. Instead of prison, he went to Portage, a rehabilitation centre in Montreal, Canada.

He spent seven months in the programme getting his life back on track, eventually becoming a drug counsellor.

These days, he says, everything he does is about his community.

His latest project, Caravan, is designed to promote peace on the island. The senior partnered with Mitchelle “Arijahknow Live Wires” Trott for it; the musician will perform wherever peace and healing is needed.

Mr Simmons thinks that if he has a weakness, it is for helping others.

“It’s genetic,” he said. “It comes from my mother, Rita. Back when I was growing up, my mother didn’t have much, but whatever she had was enough to share with someone else.”

His early childhood was difficult.

Mr Simmons was a few months old when his father, Cecil, was murdered by a fellow soldier in the Bermuda Militia Artillery.

“I was my mother’s comfort,” he said.

His mother remarried after a few years, but her second husband was abusive, and eventually left the family.

In school, Mr Simmons struggled academically and left at an early age.

One of his first jobs was helping man the elevators at Elbow Beach Hotel. He quickly learnt that hotel guests tipped well if he sang to them.

“I became known as the singing elevator boy,” he said.

As he became older, he became more involved in the thriving entertainment scene in 1960s Bermuda, performing with the Furbert Brothers and the Arpeggios.

His nicknames, “Site” and “Out-a-Site” came through performing James Brown’s 1964 song Out of Sight at the old Rosebank Theatre on Bermudiana Road. He would literally drop out of sight as he fell into a pit on stage, on to a mattress.

“People in the audience would run to the front of the stage to see where I’d gone,” he said. “Then I’d come walking back across the stage.”

It was around this time he started up another sideline — finding marijuana for visiting celebrities.

“When I was in my twenties, Bermuda really only had marijuana,” he said. “I watched it come in. There’d be these clothing stores on Front Street that weren’t really making any money. So they’d bring in things like coke and other drugs. Those shop owners were well-dressed.”

Eventually, he got caught and was sent to jail for two years.

“I came out of prison in my late 30s and I didn’t have anywhere to live,” Mr Simmons said. “I knew someone who said they had a room. They knew I was a good salesman and they wanted me to start selling [cocaine] — I made $40,000 a weekend. Now I regret it. It was the worst thing I ever did in my life.”

In 1978, he got caught up in a drug raid at a friend’s house and was arrested. He fought possession and intent to supply charges for several years, before finally losing his case in 1984.

“The whole way from Hamilton to Dockyard you could hear the wheels of the van and me screaming that I was going to kill the prison officers and their families,” he said.

At Casemates prison, an officer took him aside and gave him some advice: “He said, ‘If you go in there with that attitude, you’ll never come back off the hill’.”

It was advice that Mr Simmons took to heart.

He volunteered for day-release programmes and also took advantage of educational opportunities.

“People didn’t know it, but I was only semi-literate when I went in,” he said.

By the time he came out of prison, he had his high school diploma, could type 48 words a minute, and had taken English and sociology courses.

He was determined to help others in the community avoid the rocky road he had travelled and started the now defunct Woodshop programme, an employment scheme for former inmates.

Then in 2011 he suffered a major setback when he was badly beaten by neighbourhood thugs.

They had seen him with money he had earned from a musical production.

He was left with a broken nose and jaw and, six weeks later, found to have blood on his brain.

“I kept falling down and passing out,” Mr Simmons said. “My landlord saw me do it and insisted I go to the hospital.”

Doctors found that they had missed blood on his brain left over from the attack.

His family rushed Mr Simmons to Lahey Hospital and Medical Centre in Massachusetts, where he was told that without treatment, he only had a few hours to live.

After surgery, doctors told him he would never walk or talk again; today he walks five miles every day. Talking is not a problem.

“I am on financial assistance, but I work every day in the community,” he said. “That experience left me a lot more spiritual. I am a believer. I have grown to understand that God is in everything. Every day I get up I thank God that I am alive.”

Mr Simmons has eight children and numerous grandchildren.

Lifestyle profiles senior citizens in the community every Tuesday. To suggest an outstanding senior contact Jessie Moniz Hardy: 278-0150 or jmhardy@royalgazette.com. Have on hand the senior’s full name, contact details and the reason you are suggesting them