The Rory Winters Story Part 1: The Beginnings

To many in Singapore, Rory Winters is a an unfamiliar name, but his footballing story may be relatable. Rory was part of the English footballing system since he was 7 years old and he played professionally until he was 23 years old. He played semi-professionally since then, and then retired from the game 3 years ago. Like Victor Yanez, Rory Winters was touted for big things but he, for one reason or another, could not fulfill his potential of playing as a professional footballer. On a side note, Rory is a gem of a character, and the man has a wealth of experience under his belt. If you ever get the chance to meet him, ask him about his story – he’d be happy to share it with you.

The Story Really Begins With Preston

Rory was not born into a “footballing” family, per se. Most of his relatives were either doing something in the Arts or the Humanities, but when two-year-old Rory first kicked a football, he fell in love with the sport. However, it was when he was seven years old when he knew that he wanted to become a professional footballer. His journey began at a football camp with Blackburn Rovers.

“My dad took me down for a training session and I remember it was pissing down with rain. Basically I didn’t want to go out of the car, [because I was] scared. I’m looking over, I’m seven and they’re all nine [years old]. They seemed a hell lot of bigger than me at that age. And it was all like noise and frenetic and everything was going off. So, my dad was like ‘well, don’t get out of the car now that’s fine. No problem, but I’m not coming out here again so, it’s either now or never again.”

Rory knew deep down he had to get out of the car to take his chance and the young lad plucked enough courage to dart out of the car and onto the pitch. It would be one memory he would look back fondly on. He scored two goals that session and managed to impress enough to play along and against older boys all summer.

His time at Blackburn would be short, and Preston North End would be his next, and arguably most important, stop of his footballing career. After attending a Preston summer camp, a letter came through from the club, offering a young Rory a one-year contract.

“That was the start. Then, I progressed every year, and did really well, got moved up in age when I was 13. But when did I know that football was for me? Probably when I got to about secondary school. I realized at secondary school that I was better than most people playing it. And it just snowballed from there.”

At 15, Rory was shaping up to become a fine footballer and he got a lifetime opportunity sooner than expected. One day while having a kick around with some of his pals, his mother phones him and tells his him that he needs to get back home.

“My mother said ‘we just got a phone call from the Preston, and you’re in the team tomorrow,’ so I was went back home and it turns out to be the first-team. I was with the first-team for a pre-season final only but still, this was the season after they just lost in the championship playoff final to West Ham.

“So these guys were my heroes at 15 years old. Players like Claude Davis, David Nugent, and Paul McKenna; Some big names. So, mentally I wasn’t prepared. I was 15 in a changing room with all these guys who two months ago were playing in the playoff final. This level was miles away from where I was at. I wasn’t fit enough because I hadn’t kept myself fit in the off season. I came on the second half and we were playing against a conference national team. Well they were men, hardened men, and I was kind of like a fish out of water.”

Nevertheless, one would expect that the club had high hopes for Rory who was given his break at 15.

The End Of The Preston Dream

However, three months later, things took a significantly different turn.

“I was in my final year at secondary school in my GCSEs. And that’s when you get told whether you get a professional contracts or you get released by the club. The coach, Kevin Thelwell, called my dad to tell me to bring my tracksuit down. So, my dad thought Kevin was asking my dad to get me to wear my tracksuit so that I can sign my papers to get the deal. So, I turned up in a bright red tracksuit and the rest of my team were training at the side. I walked passed them, turned into the office, and it was ‘really sorry, but you’re never going to be Premiership level and that was what we need at this club now.’ And that’s it.”

It was a crushing blow for young Rory, who spent 8 years with Preston. 8 years of his dad driving up and down highway to all the games. It’s safe to say that the car certainly racked up a lot of miles, especially with trips to Wrexham in Wales. Till today, Rory believes that his release from Preston was a gutting blow.

“It was a massive knock to take. The way they did it; it was not great. It’s poor. There was no real follow up. They did not help me find another club nor did they help explain what level I should be aiming for. there was nothing. That was when i realized how youth football really was [in England].”

Rory also found himself at an important crossroad at this juncture. He had to choose between continuing a career in football with more trials, and going to college, where he’d do something completely different. After crying his eyes out that night, Rory made a decision and it was football.

Oldham, The Next Stop

While he was looking for professional clubs, Rory was also playing for the reputable Lancashire School Boys. Part of a stellar squad, Rory’s team was battering other counties and managed to reach the finals. Through this, Rory was still under the radar of scouts.

Oldham Athletic came knocking, and Rory signed a six-week trial contract with the club. It would be a decision that he would regret because the day after, Blackburn Rovers, who were then in the Premier League, called him up for a trial. Unfortunately Oldham were not as sympathetic to Rory and did not release him from his trial contract and Rory missed out on an amazing opportunity to potentially have played with United “cult hero” Phil Jones.

“I took it you know. Going to Oldham meant that I had to leave home at 16 but the youth teams they produced were winning everything at that level. They were consistently producing players for the first team and that seemed like the best thing to do. I signed a youth contract with them, thinking if I’m good enough later, I’ll move up.”

Rory moved to Manchester alone at 16 and lived with a foster family whilst he was there. Football became a job for him, and he entered the “dog-eat-dog world” that is the football industry. Rory couldn’t really settle down in the early stages and knee troubles during this period did him no favours as well.

At the same time, Rory faced obstacles from the club when it came to pursuing his academics. He remembers distinctively how his mom, who was a head school teacher, was shot down by the Oldham youth coach when she asked if Rory could do his A-levels and play for Oldham.

“His literal words were, ‘what do you want him to be love, a student or a footballer?’ And my mum responds back, ‘why can’t he do both?’ I think football has moved now to where having both, [pursuing academics while training] is encouraged but this was 12 years ago when it wasn’t the case. I think that put me on the wrong foot by this manager. I don’t think I was favoured at all by him.

“When he doesn’t rate you and he isn’t playing you every day becomes an issue at 16-17 years old, when you don’t have maturity to know what’s going on, or you don’t have someone with a lot of experience who can tell you to rise above it, he’s testing you.”

In his second year with Oldham, things began to click. Sometime in January 2008, 4 months till the end of his 2-year contract with Oldham. Against Huddersfield Town in a reserves fixture, Rory was deployed as right back instead of centre back and he had “the game of his life.” From there, Rory was in red hot form starting practically every reserves game at right back. From being on the fringes of the reserves, Rory was now involved with first team training and sooner than he anticipated, he was already on the bench for the first team as well.

April came, and Rory was part of the Oldham team that took on Manchester United in the Manchester Senior Cup. Coming against the likes of Craig Cathcart, Danny Welbeck, and Tom Cleverly, Rory believed he did well against such a strong side. With the day after being contract decision day, Rory believed that he had a great chance of being offered a one-year deal.

“My dad said as he was walking out of the stadium, a couple of old guys seated in front of him said that, ‘Oh that Rory Winters got something about him. It would be good to see how he does next season.’ I left thinking I’ll probably be getting the contract tomorrow and then it would be up to me to work hard again.”

What happened next was beyond anyone’s imagination.

Oldham released their entire reserves squad because they scrapped their reserve team for the following season. Rory was again clubless, and in part 2, he discusses his next chapter of a unique footballing career.