From Pai Kia to Pastor

How a former gangster turned his life around unexpectedly.
ProfilesJuly 3, 2019
The Damascene conversion is a biblical account of an unbeliever who became a believer after a divine intervention on his journey on the road to Damascus. Saul, who became the Apostle Paul, encountered god as a blinding light, and was spoken to directly by a divine voice. In a moment of life and death, Leon Chester-Stewart asked for and received a similar experience – which sent him into a different life. A story like that makes us wonder; what triggers dramatic change, and what about those of us who wished our lives could change too?

When you first meet Leon. It’s clear that he’s got a story to tell. Tall, bald, well spoken and covered in tattoos. But given his age, his tattoos do signify something other than hipster ink; you’re not at risk of him pulling you a highly technical espresso shot in a leather apron. Stay calm.

You politely enquire what he does. He tells you he’s a pastor. At that point, you’ll probably unconsciously cock your head or hold eye contact with him to see who blinks first. No one wants to be impolite now?

For me, he laughs and raises this hand “Look, I know what you’re thinking, I’m a different kind of pastor”

“I used to be a proper gangster.”

Perhaps some of us have heard of gangsters who have turned over a new leaf, become men of the cloth – that concept is not unheard of, maybe even familiar, but in most instances, we rarely get to hear the backstory of that complete 180-degree change. And for a majority of us with quieter lives, dramatic change may never come (and nor is it desired, please, we are Singaporeans). But for others – as was the case with Leon – life washes over them and change comes through the door with a battering ram, ready or not.

So, what happened?

In the beginning…

Leon was born in a loving family, and a religious one too. His mother was half Italian, half Indonesian. His dad, half Portuguese, half Scottish. While Leon had a good relationship with his dad, he had growing problems with his mum, who had the knack of giving Leon self-esteem issues by doing what most tiger mums do – endlessly comparing him to everyone else, endlessly pulling the carpet from under his feet.

This battering of his ego sent him in a constant downward spiral, and even though he went through the motions of attending church and getting socialised within that cloistered structure, he started to find more form with his “pai” friends outside of it. Life seemed more real and affirming out there; and a whole lot more fun, to boot.

He wanted independence and he wanted it fast. Growing up and getting out of his mum’s clutches was imperative. He decided to drop out after primary school and headed out into the world to work and earn his keep; it let him do what he wanted to do. He picked up a few odd jobs – the one he recalls with the most fondness was his stint as an alligator wrestler. Suffice to say, life was an interesting thrill-a-minute ride.

He got into the gangs, he got into fights – the proper bloody ‘80s Orchard Road/Far East Plaza ones. Deaths were not uncommon, and his steadfastness at the clashes meant his stock as a gang member was rising.

Life was good for a period. Coming up in the scene had all perks – popularity, free access to the more illicit pleasures of life, the lot. The power and authority he earned made up for the lack of it at home, and as with most people who got what they wanted, he developed a sense of invincibility.

Even as he decided to get married and have a family in his 20s, Leon had no plans to stand down from all that he had built up for himself. After all, why stop now? He had always scraped through by the skin of his teeth, always landed, cat-like, on his feet. This life didn’t need to end, so it was best to stay the course. In some respects, it was the easy option.

Leon pointedly recalls his open infidelity and recounts the time when he introduced his wife Lyra, to his then-mistress in a bar. The young Leon was a natural brinksman, and even in retelling the story, Present Leon still seemed awkwardly impressed with Young Leon’s gall.

Logic would dictate that their marriage should have eventually dissolved, but Leon’s mum, ever-believing that a tipping point would come, implored Lyra hang on. And now there was their firstborn, Tara, in the mix. So Lyra did.

1997 saw a sting operation on his crew that meant all homes were raided for drugs. He was out of the house when CNB officers entered his home and performed a forensic search of his place. Leon knew he was done for. There was a stash of drugs thoughtlessly left on the top of his wardrobe. He knew the score. The cane? 10 years behind bars? Maybe worse. This was going to get messy.

The CNB officer left his name card with a request for Leon to give him a call. On cue, fear turned to arrogance. Leon called the officer and, in an unthinkable, but characteristically bold move, gave him a wild telling off instead.

In a bizarre twist, everybody else was charged except him. A lucky break perhaps? Divine intervention? The officers were thorough; his mum-in-law said they searched that wardrobe top to bottom. They would have found the evidence, no question. But somehow, he’d slipped through again.

For Lyra, she hoped that this was a big enough wake up call for Leon to turn over the proverbial leaf. But it wasn’t.

Instead, it came in the form of Gino.

The Road to Damascus

Gino was the second child that Leon had with Lyra in 2000.

28 days after being born into the world, Gino contacted a severe bout of bronchitis and had to be put on a nebuliser to help him breathe. Gino was struggling for survival and this triggered an atypical panic in Leon. He didn’t want to lose his son. It was not supposed to be like this.

In a moment of helplessness, Leon made a pact with God. In the silence of his heart, he cried out for evidence of any existence: if you’re really there, prove it. And prove it now.

Later that day, Leon’s family gathered round to pray for Gino’s recovery and as a parting shot, Leon’s brother told him that Gino would be healed. He just had to believe, and at that point, Leon had no other real option. His back was against the wall; he’d made his request to the heavens. Would he get an answer? Did he even deserve one?

The next morning brought news that Gino had been taken off the support machines and was breathing normally. Overnight, Gino had made a sharp, unexpected recovery and was out of danger. Leon rushed to call his brother and tell him the good news. Putting down the phone, he slipped back to be alone with Gino.

“I then hung up the phone and went back to the ward. While gazing at Gino, I suddenly heard a clear voice behind me say, ‘Leon, after all that you have done, I still love you.’ I swung my head around to see who had said that, but to my astonishment, there was no one behind me.”

Leon was stunned. A sense of shock ran through his veins and he saw his life flash before his eyes. That same voice then spoke the same line again, just as clearly, but this time descending on his spirit more soothingly and more calmly than before.

God didn’t just answer his prayers. God had chosen to speak to him too. Deep inside Leon’s psyche, tipping point had been reached – he broke down in tears, crying in front of Gino.

Leon was now ready to call time on his fight with his mum, with society, with himself.

Life 2.0

Since 2003, Leon has been actively involved in conducting motivational talks, counselling in and out of the prisons, coaching, mentoring, and helping address matters relating to youth-at-risk. He spends most of his time in his ministry wearing two hats as both a Youth Pastor and the Executive Officer at St Paul’s church. Like some of us who may seek it, Leon has found his purpose in life.

By his admission, Leon still thinks that his previous life was a wildly chaotic and fun. He does not deny his past; he’s regretful about it but not to the point of shame – it’s inextricably linked to his journey and has given him a better viewpoint to make sense of his life now.

Given Leon’s bright, easy-going nature, it’s possible to think that he was gifted a dramatic reorientation, and has been gliding on that momentum ever since – happy ever after, if you will – but that has not actually been the case.

Leon has learned that, as with his time with the gangs, standing out a little –whether through stature, appearance or history – gets you noticed. The stigma of his past has been hard to shake. To some, Leon has been seen as a positive example of change within the church. For others, it put a massive crosshair on his back and have viewed his progress within the church less encouragingly, often questioning his motives.

“It came to the point where the politics got so bad that Tara, my daughter, wanted to walk away from the faith completely. [It was] the very thing that brought us all together. It was a testing time for everyone, but we chose to hang on. It was perhaps the biggest test for ourselves as a family after having come so far together on this journey.”

Hang on together they have, and thankfully for Leon, some of these issues have come to pass. The adventure of life continues for them as a family.

And what do his old running mates think about his dramatic departure? Are they still in touch? “Yes they are. They are happy for me and they are sad to see me go. But they are equally sad that they don’t seem to think that they have the option to make a change and move on from that life.”


It would not seem not too unreasonable to venture that for Leon, the clues to his eventual pivot lay all around him – his endless (miraculous?) sidesteps with the law; the people in his life that stood by him in the most absurdly challenging of times – change was tugging at him. Just that, for the most part, he was perhaps too blind to see it; the triggers for change drowned out by the intense noise of his life. Until he made his ultimatum with God and then got smacked in the face with the most divine of frying pans.

What about the rest of us? Do life-changing moments come as dramatically? And if they do, do we get to be conscious and aware of them as they happen, like Leon? For those of us who think that our lives could do with a shake up, no matter how mild or wild, maybe the clues for change are also lying all around us, pushing and pulling at us with the subtlety of gravitational waves. Maybe we just haven’t been tuned to pick them up. Or maybe the ability in detecting them comes from seeking them in the first place.

Maybe that’s the trick: Leon’s life may read like a distracting page-turner, but if we were to strip it bare to its key moment, it seems that the path to change came in the truthful and unfiltered asking for it. If we did so, as was with the case with Leon, it may have the power to recalibrate our wants, desires and priorities.It may make us sensitive to the things we long for beyond the noise of general life. It might set us down individual new roads, to new adventures, and give us a clearer sense of who we are. Who knows?

You would have noticed a few images with Leon dressed in road bike gear! Riding is a big part of his life and together with his friend William (himself with a colourful past), they run The Ride Spirit, a road cycling group that has been created as a safe space for people who feel vulnerable or in need fellowship. All are welcome. Check them out on Facebook here.

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