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He was devoted to his teenage boys. Then he was sent to jail — and broke his solemn vows

*Names have been changed.

SINGAPORE: James* still remembers the first time he carried his elder son, born on Christmas Eve, in his arms.

“The feeling was something I couldn’t express,” he says. “It was like a miracle.

“I told myself I’d do the best I could for him.”

James, now in his 40s, grew up with an absent father, while his mother worked full-time. As a teenager, he got involved in gangs. He was jailed twice as a young man, first for rioting and then for drug consumption.

But when his son was born, he vowed to change for the better. He swore to be different from his own father. “You can’t live the same lifestyle of the past, … still partying and mingling with friends,” he says.

Two years after Alpha* was born, Bravo* came along — his names for them when they played a childhood game. And for a decade and a half, he was indeed “a family man”, he says.

But in 2020, he ended up in prison again, sentenced to serve about four years for drug-related crimes and voluntarily causing grievous hurt.

He tells his story from Changi Prison in the final episode of the podcast Imperfect by CNA Insider. The limited series delves into the questions parents face, with heartfelt stories about dealing with parental dilemmas.

Listen: How can I be a good parent … if I went to jail?


After his children were born, James went on to run his own mobile phone business. But it failed when Alpha and Bravo were aged five and three respectively. His marriage soured, then one day his wife left after a quarrel.

He was left to break the news to his sons. “I love you as a dad, and I love you as a mum,” he remembers telling them. “Daddy will always be around.”

He took on different jobs, from security officer to delivery driver, and relied on his mother to help look after his sons.

But he made time for them whenever possible, cheering them on at school sports days and taking them for rides in his lorry. Every night, he says, the boys hugged him to sleep.

Over the years, he forged a close bond with them, and the relationship did not really change when they got older and entered their teenage years, he says.

“My boys would tell me that ‘other dads aren’t like you,’” he recalls. “They were both very proud to say their dad is very open with them and talks to them like friends.”

Even when he met someone new, the boys were happy for him. “We’ve grown up already,” he remembers them telling him. “It’s okay for you to have a girlfriend — you don’t really need to spend so much time with us.”

James got engaged, and he and his fiancée, who ran a restaurant, moved in together. He also started a new job managing renovation projects. He had a more flexible schedule and more time for his friends.

One night, he was with his friends when one of them offered him drugs. He says he does not know why he succumbed, but he did. He was caught at a police roadblock and was charged.

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Even though James knew he was about to go to prison, he did not tell his sons. “It was not something to be proud of,” he says.

With remission for good behaviour, he had hoped he could be out in less than two years, “maybe just a year” if he could get into a community-based programme. “A short sentence,” as he puts it.

But things were about to get worse. While out on bail, he was at his fiancée’s restaurant one evening when, he says, a drunken customer grabbed her. “I couldn’t take it,” he says. “I hit him with a mug.”

James continued hitting the man until his fiancée stopped him. He was arrested again.

This time round, he knew there was no chance of him serving a short stint in prison, and he would have to tell his sons where he was going. “I have to answer for what I’ve done,” he told them.

He remembers the remorse he felt at the time, knowing he was about to leave his sons — and break his promise to them. And he felt worse as he saw his boys sitting quietly, heads bowed, taking in the news.

“I could feel the sadness,” says James, who encouraged them to take care of themselves.

“If you don’t have a family, you lose only your freedom,” he adds. “When you have a family, you lose so much more — you also break the hearts of your loved ones.”

How has imprisonment affected his relationship with his sons? What is the biggest challenge he faces behind bars? And what makes him so sure this will be his last stint in prison? Find out in the podcast Imperfect by CNA Insider.

Imperfect by CNA Insider is a podcast on which young mother Lianne Chia talks to other parents grappling with dilemmas that cause them to question whether they are doing things right.

This is the final episode of this season. If you have a view on the topic or an idea for future episodes, write to cnainsider [at]

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