He emerged to tell dark stories of drug and alcohol abuse, of domestic violence and how he ruined his relationships with some of the people closest to him. And how he woke up in 2009 in a padded cell in a psychiatric hospital after taking a lot of cocaine and cutting his wrists.
Small died last week at the age of 50 of a suspected heart attack, leaving behind fragments of an often reckless life that may provide a cautionary tale on how fragile sporting stardom is. But there are also glimmers of inspiration.
"There's been low points. Life is not the easiest thing," Small said in an interview last year.
"Managed to be quite wasteful at times, and at other times, quite successful. It's a journey ... very grateful more than anything else."
Small was a member of South Africa's Mandela-inspired 1995 Rugby World Cup-winning team. The fairytale of that team has been told many times over, most famously in Clint Eastwood's movie Invictus.
The Hollywood ending isn't there in Small's own personal saga but the script is captivating.
He tried rugby as a teenager after being banned from a football league for fighting with a referee. He called it an "altercation". He later became the first Springbok player to be sent off in a test, for showing dissent to the referee. While he was ready to admit to almost every other mistake he made in life, he never budged from his position that the referee was a "one-eyed idiot — I'd like to poke him in his other eye," Small said.
His introduction to the South African rugby set-up moulded him. He'd just walked into the dressing rooms at his first junior trials when he was told he had the wrong background and didn't belong. Small was white in apartheid South Africa, sure, but English-speaking from an inner-city school in Johannesburg and not from one of the impressive Afrikaans-speaking rugby institutions.
The man who organised the team uniforms at the trials welcomed Small by informing him he was only there to "make up the numbers".
"I took that as a personal affront," Small said. "And that was me. I didn't need more motivation than that."
As a player, he was a mix of speed and determination that often presented as aggression. Highly effective but combustible.
He signed his first rugby contract at 18 after running up a huge debt playing golf for cash. He had no money, asked a team president to repay the debt, and signed for the team in return. So began the career of a World Cup winner.
He once spent his pay for an entire season on Armani suits. But his teammates also reported how he would be outrageously kind with money to strangers, often people who were down and out.
There were countless bar and nightclub episodes. One brawl at a seaside bar that spilled over on to the beach got him banned from the South Africa team.
After rugby, the bad decisions had more sinister consequences. Lost in drink and drugs after the break-up of his marriage, the suicide attempt was more a cry for help, Small said. The psychiatric hospital "wasn't a great way to wake up," he said.
Who should hear the cry? Mandela.
Small was staying with his mother in the aftermath when the phone rang. His mother answered and the person said it was Mandela calling for James. Small told his mother to hang up, clearly a cruel prank.
Mandela phoned again. Small took the call this time from the former president, then in his 90s. Mandela had taken a particular shine to the bad boy of the 1995 World Cup team and didn't forget him. Mandela talked him back from the brink.
At the time of his death, Small had moved from Cape Town to Johannesburg to be close to his two small children. He had sold a successful restaurant in Cape Town and was looking for new opportunities.
He clung to his love of rugby and cut through any drab negativity over the state of the game by saying: "I'm either too stupid or too passionate to let that faze me. I think it's magnificent. It's an incredible game."
He didn't seem to seek the spotlight but became a popular media interview subject because of his story and his style: If you asked Small a question, he gave you everything with a raw honesty. Except one question. He didn't like to be asked if he had any advice for others. "I've got enough problems myself," he said.
- AP