Veteran Lawman Bids Farewell After 40 Years of Service in the JCF

Retired Superintendent of Police and former Commanding Officer for the Trelawny Division, Winston Milton, has the distinction of serving the Jamaica Constabulary Force (JCF) for more than 40 years.

His career in law enforcement began in high school while he was preparing for his final examinations.

While studying at the Kingston and St. Andrew Parish Library, Superintendent Milton came across a career exhibition and was drawn to a book titled – ‘My Life and My Work: Life of a Policeman’.

“I was really intrigued by the book, and I decided that I would love to be a police officer. So, I enlisted,” he tells JIS News.

On October 29, 1984, a confident and optimistic 18-year-old walked into the then Jamaica Police Academy (JPA) at Twickenham Park in St. Catherine.

Just over a year after graduating, Superintendent Milton began his career in the JCF on November 1, 1985 and was deployed to the Hanover Police Division where he would rise from the rank of Constable to Sergeant.

After spending approximately 14 years in Hanover, he was transferred to Westmoreland in 1999 as a sub-officer overseeing traffic for the parish.

“I spent two years there. In 2002, I was promoted to Inspector and transferred to St. James as a sub-officer in charge of traffic for that parish. I was promoted in 2008 to the rank of Deputy Superintendent,” he recalls.

The retired lawman was transferred back to Westmoreland in 2011 as Operations Officer, and then assigned to Trelawny in 2013 in the same capacity.

He subsequently did another two stints in St. James and Westmoreland before returning to Trelawny.

“I was in Trelawny from 2017 until the end of my career in 2025. I moved from being Operations officer to being Commanding Officer. I remained until I exited the [JCF] on May 5, 2025,” Superintendent Milton shares.

Having dedicated decades to serving the nation as a traffic officer, he says one of his proudest achievements came in Savanna-la-Mar in 2000.

Recognising the significant traffic congestion in the town, Superintendent Milton and his team developed a proposal for traffic changes, including implementing a one-way system.

Despite initial scepticism from some stakeholders, they were granted temporary approval for the Christmas holiday season.

The system proved so effective in improving traffic flow that, following a study by a National Works Agency traffic engineer, it was made permanent and remains in place today.

While working in the traffic unit had its rewards, Superintendent Milton eventually transitioned into the crime portfolio to take on new challenges.

“Whilst in St. James, my then Commander, Superintendent Warren Clarke, who is now a Deputy Commissioner of Police in charge of Strategic Operations, called me in, and he basically challenged me. He said to me that he thinks I have conquered all there is to conquer, at traffic, at this level, in Area one,” he recounts.

Following their meeting, Superintendent Milton rose to the occasion and began tackling serious and violent crimes in St. James, where he was stationed.

The transition was not without challenges, and the retired officer encountered numerous heinous crime scenes – one of which still lingers with him today.

He recalls an incident involving warring gangs that left several people dead in the Retirement area of the parish, despite his team’s best efforts.

“What I saw when I got to the crime scene were two teenage boys in a living room, shot and killed… an elderly lady in her bedroom, also shot and killed, and a teenage girl, she was about 18… 19… she was also shot and killed,” Superintendent Milton recalls.

“I was in the living room with a couple of my men. Out of my peripheral line of vision, I saw movement. Then somebody just held on to me… a female… I’ll never forget that experience. She was trembling, she was the only person who was left in the house. Based on what she recounted to us, apparently, she was the intended target of that attack,” he adds.

Superintendent Milton notes that the incident was a defining moment in his operations career, instilling in him a steadfast resolve to push back against criminals.

“That particular night, honestly, it kind of put in me that determination that I would pursue criminals wherever they are and ensure that they are brought to justice,” the former Commander emphasises.

And that is exactly what he continued to do until his retirement a few weeks ago.

While he was rewarded for his dedication and passion with several promotions, Superintendent Milton says his greatest reward has been the satisfaction of positively impacting lives and communities.

“It’s like an intrinsic reward that you get when you see the faces. For example, you walk into a community that was under siege, after it has been transformed, and you get comments from persons; those comments of satisfaction and the assurance that our presence, our input, our impact have made a significant turnaround. Those, for me, are the most lasting changes,” he maintains.

Having spent his entire adult life in the JCF, the former Commander has witnessed and helped guide the Force through several stages of evolution.

He believes some of the most profound changes have been in training and the integration of technology to enhance key systems.

“At the time when I exited, a number of these systems were ISO 9001: 2015 certified. The organisation that I went to back then was a far cry from the contemporary organisation that I exited,” Superintendent Milton maintains.

The retired policeman points out that another significant change is the attitude of citizens towards the police.

“We had, at best, a very distrustful relationship. Not many persons trusted the police. I would say [the relationship was] antagonistic. It was a ‘we versus them’ culture… ‘them versus us’ from the other side. I’ve grown to see that change. There has been significant improvement in the trust level between citizens and the police during those last seven to eight years within the JCF,” he muses.

Superintendent Milton is confident that he has left behind both a stronger force and better communities through his service. As such, he has no regrets about his decision 41 years ago to join the JCF.

He firmly believes there is no greater reward than serving one’s fellow man, particularly in the critical area of security through the JCF.

Against this background, Superintendent Milton strongly encourages young people considering a career in law enforcement to sign up, emphasising the significant opportunities available in the modern police force.

“There are several areas within the JCF now that allow you to expand and grow. We have more officers within our organisation now with degrees than ever before, because of the opportunities. It (the JCF) offers careers, in terms of ballistics, forensics, IT (information technology), investigation [and] several other areas. We even have our own property management unit; if you’re a civil engineer… there’s an area in there for you also. It’s a wonderful thing to see. So, certainly, it is a viable career choice,” he states emphatically.

Superintendent Milton, however, cautions young officers not to become so consumed by policing that they neglect other aspects of their lives, particularly their families.

To drive home this point, the retired police officer recalls a poignant moment when his young son, noticing his long hours away on duty, asked if he still lived at home.

He says that moment was a critical realisation for him, underscoring the importance of balancing professional dedication with quality time for his loved ones.

As he begins his retirement, Superintendent Milton looks forward to a period of rest and relaxation after his long and demanding career.

However, his commitment to service remains strong. He plans to engage in voluntary community work, recognising that after a lifetime of giving back, he is not one to simply sit still.