Winston Alleyne: from Barbados to Britain

On 22 June 1948, the SS Empire Windrush docked at Tilbury in London, delivering hundreds of men from the West Indies. This was the beginning of mass migration into Britain, which saw peoples from the Empire, Commonwealth and beyond arrive to take their place in Britain’s post-war society and economy. Over the following decade immigration increased, and in 1958 – the same year that Winston Alleyne arrived in the UK – tensions between members of the white working class and the new African Caribbean residents broke into open violence. The worst incidents were in Nottingham and London’s Notting Hill, where attacks by white youths on Caribbean people and properties were followed by counter-attacks by members of the Caribbean population. 

Life in the UK 

With employment a priority, Winston soon found himself in the cotton mills of Oldham; a very different culture and environment to what he’d been used to. Having travelled more than 4,000 miles in search of a future, the cotton mill offered only bad pay and little chance of progression.  

His education in Barbados had been good and, although Winston Alleyne would play down his intellect, he was acutely aware that life as a cotton worker wouldn’t provide the mental or physical challenges for which he had crossed an ocean. Alone in a new country, doubts began to set in. ‘Have I made the right choice?’ he wondered, ‘Is this all it’s going to be?’  

Life beyond his working day at the mill wasn’t much better. Accommodation was hard to come by for a young man from Barbados, with many hotels and B&Bs displaying the sign: ‘no blacks, no Irish, no dogs.’ Prejudice was a daily reality, and racial tension never far from the surface. 

“Britain was the mother country,” explains Mary Chamberlain, Emeritus Professor of Caribbean History at Oxford Brookes University. “Many Barbadians knew more about the geography, history, and literature of Britain than they did of Barbados.” Despite this, Britain was a culture shock; as Winston was discovering. Only his strong work ethic and determination to succeed allowed him carry on, always ready to seize any opportunity that came his way. 

One day, Winston’s eye was caught by a poster for the Royal Air Force. It promised a career full of adventure, with good pay and opportunities for progression – everything he wanted. 

With the Regiment  

Leaving the cotton mill behind, Winston enlisted as an RAF Regiment Gunner at Catterick on 31 July 1961. At the end of training in March 1962, he was posted to the Helicopter Force at RAF Odiham, and 10 months later to RAF Gutersloh in Germany to join 230 Squadron. Over the next two years he went on detachment to Cyprus – to restore peace after strained relations between the Greek and Turkish communities erupted into open war – and to the Far East.  

By 1965 Winston Alleyne was back at RAF Odiham with the Regiment’s Ground Defence Section, but by November he was again posted to the Far East, to participate in the Indonesian confrontation.  

That same month also saw the UK’s first Race Relations Act come into force, prohibiting racial discrimination in public places and making the promotion of hatred on the grounds of ‘colour, race, or ethnic or national origins’ an offence. It was introduced in response to the increasing number of people who had moved to the UK from other Commonwealth countries, but it took another three years before another Act would tackle discrimination in employment and acquiring accommodation. 

Though the RAF was more welcoming than civilian life had been, Winston was still aware of the potential for racial tension. If he found himself in a group which contained other black service personnel he would often acknowledge the fact with a quip to pre-empt any possible tensions. “Oh the ‘brothers’ are in,” he’d joke, “people will think there’s gonna’ to be a riot!” Despite this, he was more than willing to tackle any comments head-on, and if ever referred to as ‘coloured’, would respond with: “‘Coloured’? What is ‘coloured’? Orange?” 

“‘Coloured’? What is ‘coloured’? Orange?” 

In 1966 Winston was at RAF Seletar in Singapore, before a posting to RAF Kai Tek in Hong Kong in early 1968. Travel to six countries in as many years had made good on the promise on the recruitment poster, and he had certainly found a welcoming home with the RAF. But what about career progression? 

“There wasn’t such a barrier for non-white people in the RAF as there was in certain civilian occupations,” says Alan Harby, Winston’s long-time friend and former comrade. “There was an intensive assessment system, and the higher the rank the more assessments you had. You had to get there on merit alone, as Winston did.” 

In June 1968, Winston was promoted to corporal and posted to 37 Squadron RAF Regiment at Catterick. It was here that Kenny George, fresh out of basic training, first saw Winston. The two would become lifelong friends. “He was the only black corporal on the squadron at the time,” remembers Kenny, himself a black serviceman. “He was tall and elegant and very approachable. He also had a unique quality of understanding people, which gained him a lot of respect.” 

From June 1970 to June 1973 Winston Alleyne was posted to RAF Rheindahlen in Germany. On the coach to Rheindahlen Winston met Steve Wild, an RAF motor transport river. “We were on a new station and didn’t know anybody, so we talked to each other,” remembers Steve. The pair soon became firm friends. Another friend from Rheindahlen was Kev Rushby, who remembers Winston as “a big man with a good sense of humour, easy to get along with and very charismatic.  

“He was easy to get along with and very charismatic”

“He’d always help his friends in awkward situations, but wouldn’t stand for any nonsense from us even though we were friends,” continues Kev. “He would give us the ‘Winston stare’ as we called it. He took his work very seriously, and was able to separate his professional and social life with ease. He was a steadying influence.” 

“He certainly kept me in check!” says Steve Wild. “If I’d been out all night, in the morning he’d roll his eyes and say: ‘That wasn’t a good idea, was it?’” 

Detachments to Salalah in Oman and Northern Ireland followed, before another posting to RAF Wittering, then in October 1974 to RAF Catterick to work on the Tigercat Surface to Air Missile (SAM). It was here that Winston was promoted to Sergeant on 1 January 1975.  

Having converted to the Rapier SAM system, the next decade saw Winston posted to Germany, Belize, and the Falkland Islands – being promoted to Flight Sergeant and becoming fluent in German along the way.   

A step up 

In August 1985, Winston’s hard work and record of outstanding competence finally paid off when he was promoted to Warrant Officer at RAF West Raynham – the first black man to reach the position in the history of the RAF Regiment.  

It was as Warrant Officer that Winston really excelled. “The Warrant Officer is supposed to show certain standards that should be copied or reflected upon by more junior officers and other ranks,” says Alan Harby. “Winston didn’t suffer fools lightly, but he bent over backwards to help somebody if they were genuinely in trouble. He was always friendly and encouraging to the airmen, but he knew his place as a Warrant Officer; he wasn’t ‘one of the boys”. 

Shaun Griffin was a Senior Aircraftman at the time, and well remembers Winston’s ability to mix humour with discipline. “As a 16 Squadron barman, I once cut the sleeves of my green shirt too short and tried to roll them up to hide the mistake”, says Shaun. “Change that shirt immediately!” demanded Winston when he noticed the rolled sleeves. “You look like god-damn Bruce Springsteen!” 

In addition to doling out the necessary discipline on-station, Winston also liked to nurture talent in others, and would always have an encouraging word. “I never once heard him be critical unless it was constructive criticism,” remembers Alan Harby. This outlook was also evident in Winston’s home life. “He’d say ‘You’ve got try your hardest, don’t give up, keep going and always strive for the best,’” says his daughter Sara-Eden. “And I could see that he himself had done just that.” 

Six months after his original promotion Winston was again elevated, this time to Squadron Warrant Officer. Here, Winston found himself even more deeply involved with the maintenance of discipline and the general smooth running of the squadron. “Officers decided what a squadron should be doing,” says Mac MacDonald, Station Warrant Officer RAF Honington, “and the Squadron Warrant Officer decided how they would do it.” 

“The whole squadron’s discipline, ethos and tone was set by Winston,” adds Shaun Griffin, himself now Corps Warrant Officer in the RAF Regiment. “He had exacting standards that were enforced at the door. 

“A little bit of me as a Warrant Officer will always be the type of Warrant Officer he was,” Shaun continues. “He left an indelible print on my DNA as an NCO and then subsequently as a Squadron Warrant Officer.” 

“He set the bar for other black Regiment airmen.” 

Having arrived in 1958, young and alone in a country beset by racial tensions, Winston Alleyne retired from active service as Squadron Warrant Officer in 1996. On his chest were the Military Service Medal, the UN Medal with clasp (Cyprus), the General Service Medal with clasp (N Ireland), and the RAF Long Service and Good Conduct medal with clasp. 

His second career involved working in a unit to support people with complex needs, where his mix of compassion and discipline inspired even the most difficult-to-manage residents. Winston Alleyne passed away in 2020. On learning of his death, Air Commodore Scott Miller – Commandant General RAF Regiment – noted that Winston was simply “an RAF Regiment legend.” 

Warrant Officer Balbir Singh Flora MBE, of RAF Recruitment and Selection’s Communities Engagement Team. Says: “The RAF today has aspirations to be diverse and reflect the society it serves. In order to do that we are looking at ways to better promote our roles by making sure all our advertising shows the diversity we already have. This helps attract a more diverse workforce who think differently and have different ways of processing information. This difference could be the edge we need when resolving critical or urgent problems. The RAF is increasing awareness of the careers and opportunities it can offer to all, regardless of race, gender or background.” 

Main image: Winston Alleyne as Warrant Officer. © Sara-Eden Ludwell