You may think that a footballer becoming a lawyer specialising in sport off the back of a career in the professional game would all be part of some grand plan.
David Winnie, after all, knows the game. He knows what it’s like to be a player, and how to deal with agents. He has the qualifications. And he still has, what he modestly calls, ‘his little black book’ of contacts from within Scottish football and further afield.
But Winnie learned long ago that sometimes, life doesn’t care about your plans.
When he was starting out at St Mirren, Winnie was one of the Scottish game’s hottest properties. He could have gone to university, but then Saints boss Alex Miller persuaded him to give full-time football a crack.
And don’t get him wrong, over the piece, he was glad he did. Even though he was entering a world where, as a callow youth, his naiveite would soon be exposed.
“Tony Fitzpatrick once got on at me for trying to put a bandage on my knee before a game,” Winnie recalled.
“He said, ‘what are you doing?’ I said, ‘well, I'm getting this on my knee’.
“’No, no, no, you don't do that,’ he says. ‘You might as well just put a big X on your knee. Take it off’. And that was the mindset.
“To be honest, it was a bit like being in the army.”
On the pitch too, he felt a little out of his depth to begin with.
“I think it was about my second or third game as a professional player, I played against Aberdeen when I was 17,” he said.
“Aberdeen had won the Super Cup not long before it. They were arguably the best team in the world at the time. Crazy. I think it was two or three-nil at Love Street, and they just picked us apart.
“I thought to myself, ‘well, that is what it takes to be a professional football player’.
“I didn't realise at the time that I already played the best team in the world that day, you know, that's what they were at the time, they were a fantastic team.”
Winnie would have given you long odds that afternoon that he would one day be part of that side. But he still had plenty to achieve at Love Street first.
Having found his feet, Winnie would go on to be part of the St Mirren side that lifted the Scottish Cup in 1987, and one of the youngest captains in the Premier League, as it was at the time. As he led the Saints out to take on champions Rangers at Ibrox on the opening day of the 1989/90 season, he was on top of the world.
Clubs from England were sniffing around him, and he would have surely impressed them that afternoon. But life had other plans.
Winnie was oblivious to the nightmare that lay ahead as he celebrated with the St Mirren supporters following a sensational win for the Buddies.
“I'd been flying, I'd been doing really well,” he said.
“We go to Ibrox on the opening day of the season, us against the champions. They unfurled the flag and all that, and we beat them.
“I was cock-a-hoop, and there was talk of going down to the Premier League in England, fees being discussed, all that type of thing.
“And then, the following day, the Sunday, I got told by the doctor that my mother had about five months to live.
“My dad had died in similar circumstances when I was a young boy, so your life goes from literally being on top of the world one minute to being floored the next.
“With that, over the next six months or so, I mean, my life fell apart.”
With that devastating diagnosis, Winnie’s veneer of invincibility was shattered. Again, Tony Fitzpatrick provided counsel, but this time, it was never going to be as simple as shrugging off a knee knock.
He may have been taught to hide any signs of weakness or vulnerability at all costs, but Winnie knew he was in trouble.
“I spoke to Tony about it, he was the manager by that time,” he said.
“I said to him that to be fair to both him and to the club, it might be better if I were to walk away from the game for a bit, just until this period of time sorted itself out and I knew what was happening.
“I had to look after my mum at that point, until she died, in effect.
“But he said no, he would try to help me with it. I was the captain of the team, and I was on the pitch, but I wasn't really there, if you know what I mean? I was a million miles away. Physically, mentally, I was nowhere at it.
“When my mum died, my contract at the club had just finished as well, because it was in June 1990. And at that point, I wasn't going to stay at the club anymore, my time there had finished. I'd been there 10 or 11 years, man and boy, so I knew it was time for me to go.
“But I had no appetite for the game, to be honest. It was just coming from my mum dying, the same as my dad had gone a few years before.
“I was trying to figure out what I was going to do with my life.”
At that point, Winnie could have been lost to the game. But after being given such a rude awakening by Aberdeen all those years previously, life had another twist in store.
“I literally had stepped away from football, so Premier League teams in England weren't going to come and take a look at me,” he said.
“Aberdeen stepped in that November, and they were a big club at that time. There were a lot of big players there. Willie Miller was still there, Alex McLeish, it was a big, big club, and they were challenging for the league every year. They were one of the teams to beat.
“I suppose in hindsight, I don't know whether I should have taken the move or not at that time, I really don't know. It was hard to turn down.
“I'd gone from a situation the previous summer where I'd had several Premier League clubs in England coming in and said my club knocked back offers, to six or seven months later when I literally stepped out of the St Mirren team, and it was just circumstances beyond my control.
“It's viral, you know? And with that, teams just weren’t coming in to take me.
“So, I had to take that offer, but in hindsight, should I have stayed at St Mirren? I really don't know.”
Arriving at Pittodrie in those days for any player was a daunting experience, but for one who hadn’t played in months? That brought an added layer of anxiety for Winnie.
Thankfully, his new manager was willing to be patient, knowing the talent he had on his hands if he could get him back to a good place, both physically and mentally.
“To be fair, Alex Smith, he was the manager at the time, he knew my situation, and he allowed me the time to settle up in Aberdeen,” he said.
“It was the following season when I started in the team, and we started really well. We were sitting first or second in the league, challenging everybody, and then, I don't know, for whatever reason, come December, January time of 1991, things just took a dip, and we couldn't pick up again.
“At that time the fans at the club were really, really demanding, nobody was to beat Aberdeen at Pittodrie, nobody. Not even Celtic or Rangers.
“When that kind of thing happened, there were major ramifications for the manager and the players, such that Alex got the sack.
“He brought me to the club, and then it was all change again.”
As grateful as Winnie was to Smith, it didn’t necessarily seem as though that had been the wrong move from the club, at first anyway.
“Willie Miller came in as manager, and things actually started really well for the team and myself at that point,” he said.
“But Rangers were a really strong team too. We finished second to them in the Premier League, the Scottish Cup, and what was called the Skol Cup that year.
“Any other year, we would have won the treble. But we just couldn't take that next step to beat Rangers.
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“I mean, they beat Leeds in the European Cup, and they got to what was effectively the semi-final of the Champions League, so they were a great side. But we weren't far behind.”
In those days though, the notion that second place was as good as last extended beyond Glasgow and into the Granite City.
“Because of the demands of the supporters at the time at Aberdeen, they were expected to go and win the league and everything else the following year, and it didn't happen,” he said.
“Willie Miller, he didn't have anywhere near the funds that teams like Rangers or Celtic had at the time to go out and buy players, it was a shoestring compared to what they had. We just couldn't match them.
“The standards that they had as a team, and as an institution. To see them now, it’s a totally different beast.
“It was a difficult time for the players, because the fans would probably take a bit longer to adjust to the new reality that Rangers were bringing in guys who were way beyond Aberdeen's reach. Celtic were starting to play catch up with that, and the two of them were starting to pull away.
“The fans took a long time to adjust to the fact that they weren't in that elite bracket anymore. They couldn't accept it, and it was difficult for the players at Aberdeen to deal with it as well.
“Any player coming up to the club at that time, they were reminded of the success, because you could see it on the walls when you walked through the corridors, what they'd done and what they'd achieved. But to get to that level again was another thing.
“There were a lot of ghosts that walked through those corridors. You could feel them on your shoulder, every player could feel it.”
By 1995, after four years at Pittodrie, it was time once again for Winnie to move on. He had short stints at Hearts, Dundee and then back where it all began at St Mirren, but he was itching for a new experience.
The option he chose would be life-changing, in more ways than one.
“I had been in Scotland long enough,” he said.
“I just had to get out of the place at the time and I went out to Iceland to play.
“I'll be frank; I thought my career was winding down. I thought I was going to be playing with a bunch of fishermen and farmers.
“I went to Reykjavik, and I was expecting nothing. But I’m at my first training session and I threw the ball in to this young boy.
“I was about to apologise, because it was a poor throw, but he took it down on his chest, turned and rifled it into the net. I thought, ‘this boy can play’. It was Eidur Gudjohnsen. And he wasn’t even the best player in the team.”
Winnie would soon be startled in a more profound way, though.
“I mentioned before sliding doors in a negative sense, this was one in a positive sense,” he said.
“I was walking out of a bar, and the woman who is now my wife, Heida, was coming into the bar and we literally bumped into each other.
“So, Iceland definitely had a positive effect on my life in that regard. I should say that! I've two sons who have dual nationality, Icelandic and UK. So yeah, it's had a very positive effect on my life.”
It seemed for all the world that as his playing career wound down, a seamless transition to the coaching side of the game awaited.
As manager of KR Reykjavik, he won the Icelandic title and competed in the Champions League qualifiers. When he eventually came back home though, while grateful for the opportunity, part-time Dumbarton in the third tier were the only ones to throw him a bone.
“I was lucky I got the job at Dumbarton, but I was becoming increasingly obvious to me that it wasn't for me,” he said.
“I wasn't enjoying it. And particularly, the part-time side of things. You've got the players two nights a week. It's difficult to change things dramatically.
“I wasn't enjoying football anymore, and I came to the conclusion that coaching was not my thing.”
The part-time aspect of the job though actually worked in his favour, allowing him to eventually return to the studies he had abandoned on the cajoling of Alex Miller all those years before.
“I'd always wanted to go back and study,” he said.
“But it wasn't one of these things, ‘I want to be a lawyer and save the world’. I went to the university, my local one, in Paisley. And I'd looked at the prospectus and I was left with law and economics. I thought, ‘well, I’ll give it a bash’. And it just went from there, really.”
After gaining his degree though, Winnie found opportunities in his homeland hard to come by. And his then girlfriend, Heida, was working in London.
“In my football career, in terms of coaching, I was going nowhere,” he said.
“With managers, you get one or two bites of the cherry and if you make an arse of it, you don't get another chance.
“That was the push factor. And the pull factor was, that my wife to be was working in London. So, I thought, I'll take a chance, why not? I’ve nothing to lose.”
And as it turned out, everything to gain. There was of course the small matter of having to cram an English law degree into just eight months (“I wouldn’t recommend it,” he says), and then finding a job amid the financial crash.
He landed on his feet once more though, and with the burgeoning spending power of what was now the behemothic English Premier League, he noticed that there was a huge demand for a man with his unique skillset.
“I'd realised particularly down here in London, that there was a big market for the sports side of things that started to take off,” he said.
“Sports law is a bit of a misnomer, but that's the legal side of the sports industry.
“I got a job at one of the big firms and it just went from there, really.”
It has now led to Winnie becoming a partner in Scottish law firm, Gilson Gray, where he is now bringing his expertise to bear north of the border too.
“Although we acted for sporting individuals and entities prior to me arriving, we have now got several other clubs on our books, which is great,” he said.
“I'm still based in London, but remember that wee black book? There was a big section of it devoted to Scottish contacts, which over the years I had neglected to an extent because of working here. I’m now opening those pages again. And it's good to go and meet these people again.
“There was a vague notion in the horizon. I could see it, and it was like a sunrise, the more I was walking towards it, the brighter it was becoming.
“It tied in nicely with the fact that well, I've had one career, and I'm going to have to abandon it and start all over again. I didn't have to do that, I could use the knowledge and experience of that previous career to help me with the next one.”
Winnie’s days now are spent assisting clubs with the movement of players, disputes with other clubs over issues like transfers fees and training compensation, and he will soon be working with worldwide arbitration body, Sports Resolutions.
There are still ties that bind him to his roots though, and as has been a theme for Winnie, life had another surprise for him recently. This time, it was another pleasant one.
“It just so happened that I was on holiday in Reykjavik when St Mirren played Valur,” he said.
“I met up with Tony. We had a coffee and spoke about old times, which was great.
“We do still keep in touch, you know, the boys that were at St Mirren, and some of the guys I played with at Aberdeen as well. But I'm not sure the bonds are still there with teams these days.
“I think it's just because of the movement of players, the movement of workers as it were. It’s much greater today than in my time.
“There isn't that same connection, I don't think anyway.”
Winnie is grateful though that his new life is keeping him connected with his old one.
