Gangster uncles, drugs and family despair: Why Prisons' deputy commissioner is a firm believer of second chances

Fresh out of university and armed with a degree in hospitality and tourism management from Nanyang Technological University, Mr Matthew Wee Yik Keong was searching for a people-oriented role in sectors like human resources and social work.

However, it was an advertisement for the Singapore Prison Service (SPS) that caught his eye and steered him to a path he’s been journeying on for the past 26 years.

It had “Bring with you your ideals and compassion… we do not promise you an easy job, but we guarantee job satisfaction. Shine and be a light in someone’s life.” emblazoned over an image of an illuminated forest.

“I can still remember the words that were on it. I applied for the job, and the rest is history,” says Mr Wee, 50, who is now the Deputy Commissioner (DC) of Prisons (Operations and Rehabilitation).

While the advertisement's message resonated deeply with DC Wee, his decision to join the Prisons was also influenced by personal experiences.

"Three of my uncles were gangsters and drug addicts. They were constantly going in and out of jail decades ago, and their lives ended tragically," he shares.

"Witnessing the impact of their actions on their families and how their lives ended prematurely left a deep impression on me – it made me want to help others avoid the same fate.

“I remember them as loving fathers to their children. So I suppose I have always wanted to understand this darkness and trauma surrounding them."

In his role today, DC Wee oversees over 10,000 offenders, and he is bent on helping them transform their lives by creating a positive cycle of change.

In my current role, I oversee all operations and rehabilitation aspects of the penal and drug system. My work impacts over 10,000 offenders, about 50,000 family members and every Singaporean indirectly.

Last April, we rolled out our Corrections 2030 master plan and the next few years are going to be very exciting.

We will be working on expanding and strengthening SPS’ rehabilitation programmes for inmates by leveraging technology and community partnerships.

This includes the uplifting of inmates’ families to help break the cycle of re-offending and intergenerational offending, and boosting training and employability of inmates and former offenders.

Another focus area would be smart prisons. For example, we are making our prisons smart by having our security cameras and systems embedded with artificial intelligence and machine learning. This helps us to achieve the best possible safety and rehabilitation outcomes for the inmates.

I began my career in 1998 as a fresh graduate, undergoing four months of mandatory training where I learnt about the legal framework, tactical as well as inmate management skills. Initially assigned to a correctional unit managing 400 inmates, I oversaw daily operations, including discipline and rehabilitation matters.

In 2000, I moved to prison headquarters, focusing on corporate planning and strategy while pursuing a post-graduate diploma in social work at the National University of Singapore. I was sponsored to do a master's degree in public policy at the Lee Kuan Yew School of Public Policy in 2005.

Returning in 2006 as a Superintendent in a maximum security prison, I was responsible for 900 inmates and 100 staff.

My career progressed through various leadership roles, including Director of Corporate Communications, Director of Community Corrections Command and Commander of cluster A where I oversaw 5,000 inmates and 600 staff.

I have also completed two secondments: One to the Ministry of Home Affairs as a Deputy Director overseeing penal, drug and civil defence policies, and another as the Chief Executive Officer (CEO) of Yellow Ribbon Singapore (YRSG), managing initiatives to upskill inmates and help ex-offenders secure jobs to reintegrate successfully back into society.

I also concurrently served as the CEO of Yellow Ribbon Industries, a fully owned subsidiary of YRSG that operates various businesses to support the reintegration of ex-offenders.

Before returning to my current role at SPS last year, I completed a Stanford executive programme at the Stanford Graduate School of Business.

It is the ripple effect of change. In SPS, we do not just aim to rehabilitate inmates. We aspire to be a social enabler, help them reintegrate into society, and the impact extends to their families and the wider community.

During my time at a maximum security prison, I worked with an inmate serving a 10-year sentence who had a young daughter. Responding to his desire in upgrading his skills, we assigned him to a call centre job in the prison.

After completing his sentence, he not only started his own call centre employing ex-offenders but also founded a charity to help single parents, divorcees and persons with disabilities. Recently, he sent me photos from a holiday with his daughter.

That is the power of second chances – when you turn one life around, you have one less victim of crime. Seeing how the work we do transforms lives and creates a positive cycle of change is what keeps me going.

I've spent over half my life in prison and I love what I do. I found my purpose. This is where I belong.

The emotional aspect of the job caught me by surprise.

Although our training equipped us with the skills and knowledge to be a prison officer, I did not realise how much emotional strength was involved.

In my first week, I had to escort an inmate to his father’s funeral. Seeing the emotional reunion between him and his family was heart-wrenching.

While I've maintained composure in front of inmates and colleagues, the emotional impact often hits later when I go back to my office or home.

It really helps that my wife is also a prison officer. We met in SPS and can perfectly understand what each other is going through and better support each other. Sometimes, we decompress by exercising, going for runs and long hikes together.

Because of all the TV dramas out there, people think that working in prisons is dangerous. That is not true in Singapore. SPS officers are well trained to handle any situation, and most inmates just want to serve their time and become better.

As prison officers, people also often assume that we must be fierce, and that inmates and officers have this antagonistic relationship.

It is the responsibility of the officers to take care of the inmates. They are the first points of contact if the inmates need help, like if something happened at home, or if they want extra visitation time to carry their newborn baby.

We connect as human beings at a very fundamental level, but at a professional level, we treat the inmates fairly and with empathy.

Another misconception would be that work here is boring. But since joining SPS, I have been given many opportunities that are beyond my imagination.

I have attended overseas conferences about correctional work, met foreign counterparts to exchange notes, got invited to share the good work we have done in Singapore at the United Nations in Vienna and engaged with government and non-governmental organisations (NGOs) in countries like the US, Japan and across Europe and Asean.

Good communication skills are essential. After all, it's a very people-oriented industry.

Inmates face a lot of challenges – addictions, mental and physical health issues, financial and family problems, jobs and so on – so you need to have that ability to connect, listen and communicate.

Being vigilant and having the ability to think on your feet are critical skill sets for prison officers. By staying alert and ready to anticipate potential issues, officers can stop problems before they start, calm things down if tensions rise and react quickly in different scenarios.

It’s really about the range of problem solving abilities and soft skills, because the hard skills like tactical proficiency and physical fitness can be picked up at the training institute.

One thing that I would a​sk is: Do you believe in the power of second chances, fresh starts and new beginnings?

Working in prisons and the field of corrections can be challenging – there is emotional heavy lifting involved, on top of mental strength and the physical demands of the job.

However, as Captains of Lives, as SPS calls its officers, we are trained to mentor and guide inmates towards leading a better life that is crime-free, where they can find happiness and give back to society.

We don't promise you an easy job, but we guarantee growth, fulfilment and, like what the newspaper advertisement that I saw 26 years ago said, tremendous job satisfaction with a deep sense of purpose.