He agonisingly missed out on a Premier League title with Newcastle in 1996, played in a critically acclaimed Northern Ireland side who never made it to a major finals, and battled a gambling addiction which saw him lose £7 million over his career as a professional footballer ... and still Keith Gillespie says he would not have done anything differently if given a second chance.
The News Letter spoke to the former Northern Ireland international as he launched a new career as a football agent, hoping to lead others away from the perils that dogged his own playing days.
Asked if – with the gift of hindsight – there was anything he would have done differently at any point of his career, Mr Gillespie said: “I’m a great believer in what will be, will be. I think things happen for a reason.
“I’ve been very fortunate to have played so many games for some great clubs and represented my country on many occasions.
“For me, there ain’t really much point looking back and reflecting on whether I should have done this, or whether I should have done that. It’s in the past.
“The things I went through in my career – the highs and the lows – they are the things that determine you as a person. I’ve had plenty of ups and downs and come out the other side a stronger person.”
Asked how he felt about Northern Ireland’s qualification for Euro 2016 having never qualified for a major tournament with the national team himself, Mr Gillespie said: “There is disappointment in terms that I didn’t manage to get to a finals because I think the side we had in the group with Spain, Denmark and Sweden (Euro 2008 qualifying) were outstanding in that group apart from a couple of games that let us down.
“I was a Northern Ireland fan first, then I played for them and then I became a fan again, so I was delighted that we’d managed to qualify. It’s been an amazing period for the country.
“Michael O’Neill has got everyone playing with a lot of confidence. Our problem in the past was that we would have done well against the bigger nations and we would have slipped up against weaker ones. He’s put a stop to that.”
Of what he described as the most enjoyable period of his career with Newcastle, Mr Gillespie said: “Everyone says the league table doesn’t lie at the end of the season but for me, the best side didn’t win the league that year (1996).
“Anybody involved in that Newcastle squad would have regrets. It was just a shame we couldn’t get over the line.”
He said he had an affinity with all the clubs he has played for – a list which includes Blackburn Rovers, Leicester City and Sheffield United as well as Glentoran – but added that his first love was Manchester United, the club he signed for as a teenager.
In his book – How Not To Be A Football Millionaire – Mr Gillespie talks frankly about his battle with alcohol and gambling which saw him declared bankrupt in 2010.
Speaking with calm assurance, he tells how he has taken control of his past demons.
He said: “I’d still have a drink and a small bet but it’s not something that happens very often.
“If I’m with friends and having a drink on a Saturday afternoon I’ll maybe have a little bet watching the football.
“Football bets were never the problem, horses were the big problem for me. It’s something I shouldn’t have got involved in but I was very young and naive and had a lot of time on my hands. That’s how it started and then escalated.”
Keith Gillespie has teamed up with Banbridge businessman Brian Adair to form a new football agency – OneTwo.
As an agent Mr Gillespie said he believed his experiences could help other players.
He said: “My family and my agent helped me through a lot of ups and downs. That’s a role agents have that people don’t see. It’s not all about sorting a deal out.
“Professional footballers can be very vulnerable. It’s important they have the right people to speak to.”
Mr Adair, who had trials with Coventry City and is best known for his time with Loughgall, commented: “We’re here to guide players and to ultimately give them advice that’s going to develop their career. That comes because we’ve a passion for the game and a passion to do well.”