Released by Oldham and without another club at 18, Rory was faced with several tough decisions. Does he take a gamble and continue pursuing his footballing aspirations? Or, does he give up the footballing dream and concentrate on school? Rory had always believed journalism would be a viable alternative should the footballing dream ever fail to materialize.
Yet, as much as journalism proved to be a viable alternative, his first love had been, and still is, football.
“I wrote a letter to every single professional club in England; every professional club in Scotland; just asking for trials to simply to prove myself because I knew I had something; I had been playing well [at Oldham]. I had that fire in my belly again but even more at 18 with a bit more maturity. Watford were the the only club that got back to me and that was a letter that said, ‘thanks, but no thanks’ because they had their squad finalized. They did say they’d keep me in their database. I appreciate that because they were the only club that ever did get back to me.”
Amidst the lack of interest from clubs, Rory’s mother suggested Rory enrolling into Cardinal Newman College, a college in Preston that had an excellent footballing program. The late Sean Haslegrave, an ex-pro that Brian Clough signed for Nottingham Forest, ran the program. Under Haslegrave, Cardinal Newman’s football team was regularly challenging for National Honours.
“He was old school, to say the least. As a coach, there was like no messing with him but he had a way of making it work. He talked to me in our first meeting and he asked me what I wanted out of this. I said I wanted to be a footballer again. [Haslegrave] said, ‘I’ll do whatever you want to bring you back to that level as long as you work hard for me.’ I don’t think men like him exist anymore.”
Through Haslegrave and playing for Cardinal Newman, Rory managed to get trials with a few clubs. After trials with Accrington Stanley, Stockport County, and Morecambe, Rory was due for trials with Wigan Athletic, Blackpool and Chesterfield. However, Morecambe offered Rory a pre-contract agreement where he could play with the Morecambe reserves until he finished his ‘A’ levels and a one-year professional contract thereafter. Rory was not about to let the opportunity slip and duly signed the agreement.
Morecambe and England Under-19s
Football would dominate his entire life during this period. Rory had to finish his ‘A’ Levels but he was playing for Morecambe reserves every week as well as the England Under-19 School Boys. Effectively his social life became non-existent, and trainings replaced his daily schedule.

“I went and represented England and we wore the official England kit and got caps. We managed to get to an international final in Rome, Italy. The lads who played in that team were very very good players. I just saw that you could combine football and academics quite nicely. We had David Accam and Abdul Majeed Waris who both went on to play for the Ghana national team. Abdul Waris played in the 2014 World Cup for Ghana and David Accam is a star player in the MLS.”

The year at Morecambe, featuring for the reserves team, was a fantastic experience for Rory who relished his playing time. However, when he signed professional terms with the club, things took a different turn again.
The start of the season went well, with Rory featuring in many of the pre-season games. He fondly recalls marking Jay Rodriguez when Morecambe played against Burnely in a pre-season friendly. However, when the season came around, the Morecambe manager decides to go for the senior players.

“I understand that its League Two. It’s cut throat, blood and guts and everything else. I’m a skinny lad at 19 [years old] as a centre-back. So, I went out on loan to Vauxhall in the Conference North. I did well and came back. Then, i went to Kendal, which was a level below that. [At Kendal,] we had a great run in the FA Cup. So I came back, sat on the bench for Morecambe a few more times but didn’t get on. Morecambe, that year, had one of their most successful years they’ve ever had and were going to the League Two playoffs.
“I remember going to the manager, Sammy Mcllroy, who is a Man United legend, and knocking on his door. He tells me, ‘listen, I can’t put you in the team because we’re chasing the playoffs. We’re not secure. When we get in the playoffs, then maybe I can give you a couple of games.’ And then we scraped in the playoffs I think in the last couple of games the season it wasn’t like. It wasn’t like they had five games spare where I can come off the bench or start games. So, i didn’t play a game. i was on the bench constantly. I went out on loan again and then came back. From there, i didn’t even get released. My contract just expired and no one said anything. That’s how they treat you. you are a piece of meat and that’s it.”
The Journey Man Phase Begins
Rory struggled with this reality but realized that his footballing dream in England may have come to an end. University was naturally the next best option for him, but the application window usually ends in January and it was already May when his contract with Morecambe expired. Rory somehow managed to get a spot at a university but he was doing Sports Science, something he had little interest in. Rory had always wanted to do English. He loved to read and write, and English would have been the perfect major. But Rory did not want to wait around till the New Year.
“I had offers from America to go on a scholarship but I didn’t take it. If I had, I would have to ‘red shirt’ because I previously signed a professional contract and I would have to sit a year out. I had my mates still around in my town. My network was [in England].”
While at University, Rory played semi-pro with Rushden and Diamonds and was, in fact, earning more money than he was as a professional. Yet, after the completion of his degree, an opportunity to play in North America came knocking on Rory’s door again. This time he answered it.
Rory played in America and then Canada through summer, and through his experiences there, he learned how football became a passport to travel. It dawned on him that he didn’t need to remain in England to make it as a footballer.

In the United States, Rory turned out for the now defunct AFC Cleveland and FC London in Canada, who were in fact the reigning National Champions when Rory arrived.
Rory remembers how “they were the best team in the league by a distance.” He still wonders how many of them still have not turned professional because they definitely can thrive at that level.

His experiences in North America helped reignite his love for football and also motivated him to pursue higher education in the field. Rory would head to complete a fully paid Masters in coaching. As long as he turned out for the University football team, his tuition fees were covered.
Stepping Into a Coaching Role
It was at Gloucester where his passion for coaching began to take root. It wasn’t just coaching in football that Rory gained an education in. His time at Gloucester equipped him with diverse life and business coaching skills.
Besides acting as a real eye opener for Rory personally, his Masters also helped open a management pathway for Rory. He secured a job as an athletic development manager and he was responsible for all the academies in Southwest England.
A stint as a sports teacher soon followed, and whilst teaching, Rory signed with Kendal yet again. As much as he tried, he couldn’t escape the player within. It was not easy to balance work and playing though.
“It takes a massive toll on you. You know, we’re playing on Tuesday night away in Kidderminster which is a six-hour journey. You have to miss half a day’s work. Yeah, so I had to get a written letter off the head teacher to allow me to do it. Then I get back at 4am. And since I’ve played, my body really feels the beating it’s received. But you got to go back in the next day and deal with kids.”
But why did Rory become a PE Teacher? Did his mother, a teacher herself, have anything to do with this?
“I saw it as a typical route of a failed footballer to go on to be a PE teacher. I wanted to develop other people and it was really amazing working in that school. One of my former students came to me as a eleven year old kid and is now seventeen turning out for Aston Villa and was linked with Man United and Liverpool. When I coached that school team, I found more joy in that than I ever did played.”
In the final part of this series, we look at Rory’s time in Singapore thus far and his thoughts on future plans.
Featured Picture provided by Rory Winters
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