One afternoon he added up how much he had squandered during the course of his professional career. It made for uncomfortable reading...
Manchester United £60,000
Newcastle United £1,102,000
Blackburn Rovers £3,510,000
Leicester City £1,050,000
Sheffield United £670,000
Bradford City £15,000
Total (plus extras) £7,215,875
That day seemed a world away from 1993 when he burst on to the scene as a fresh-faced young star with Manchester United. A dark-haired lad from the streets of Northern Ireland with a God-given talent, he was dubbed the new George Best.
One of the famous Fergie fledglings, he made his debut aged just 17 before moving on to Kevin Keegan’s Newcastle where he came so close to landing a Premiership title winner’s medal. International caps piled up too.
It was a thrilling adventure. Flying down the wing and sharing pitches and dressing rooms with legends, but behind the success and glamour, it was a different story.
Like Best, Gillespie had a talent for self-destruction. He liked a drink and there were women but they weren’t causing a big problem – it was keeping hold of the millions he had earned from the game that ultimately proved his downfall.
It wasn’t just about gambling. A nightmare ordeal during a training break in La Manga landed him in jail for a crime he did not commit. Then, in 2010, Gillespie became headline news again when a series of flawed business deals saw him declared bankrupt.
How Not To Be A Football Millionaire is one of the most honest autobiographies you will read, about a player who lived the football life to the full.
It tells a fascinating and moving human story of the darker side of the glory game.
About winning and losing, fortune and fate, hope and heartache...
About having the world at your feet and being left to ask yourself: ‘Where did it all go wrong?