There is a beautiful 23-year-old girlfriend and a house built to his own specification, named "Camp Nou" after the stadium where he helped Manchester United win the European Cup. He is tanned, blond and the only pounds he is piling on 18 months after retirement from football are the ones he has just won – all 40,000 of them – at a poker tournament. Having turned down the chance recently to buy a £220,000 Ferrari ("not convinced"), Teddy Sheringham climbs into his Bentley Speed and sets off in dazzling sunshine for a pro-am golf tournament in Essex. Teddy, where did it all go right?
Talent, you could say, determination and that occasional little bit of luck that every sportsman needs. All three came in handy early on when the son of an East London policeman was trying to make something of himself. Crystal Palace and Tottenham – costly mistake that one – had turned him down before a Millwall scout was impressed by the wiry striker's performance in a youth game for Leytonstone & Ilford. He signed as an apprentice, scored in his second senior game aged 17 and finally called it a day a quarter of a century later, coming on as a substitute for Colchester United's last game at Layer Road.
Convinced now that "there's more to life than football", he is enjoying the financial freedom available to successful players of his generation and is reinventing himself on the golf course and, especially, at the poker table. Last week's stunning success in the PokerStars European Poker Tournament in London turned him further away in fact from his former sport, since his continuing progress there meant he was unable to work at United's Champions' League game against Wolfsburg for ITV, who have told him not to bother again.
It may be an unusual career choice, but there are echoes in the card sharp of the guile, quick thinking and, yes, stubbornness that always refused to regard setbacks as anything but temporary. "I was always a gambler," he said. "Playing golf I'll have a bet on myself, or at table tennis I'll want a wager on it. At poker, the skill levels and understanding of the game is just immense, but you only learn by losing money. Luckily for me I was still being paid by football clubs at the time, but it still hurt that I was going to play with people looking at me as if I was the mug. 'Here he comes again, make him comfortable, give him a sandwich and we'll take his money'."
Card skills – albeit three-card brag rather than poker – were first honed on the coach to Millwall away games, happy days in the late Eighties when the club once led the top division. But football days were always happy ones for Sheringham, even that final match at relegated Colchester. "I've got great memories of every club I played for. Down at Millwall it was fantastic coming through the ranks, people questioning if I could go on to the next level. Then loving a quick year at Forest with Cloughy." Even after a disconcerting start: "He said, 'You're Edward Sheringham are you?' I said only my mum called me Edward and he went 'Welcome to Nottingham Forest, Edward', turned round and walked off."
Should he ever go back into football, there will be an impressive range of experiences for club and country to call upon: "Cloughy was a little bit past his best but his views were still easy to follow: there's only one ball, win it and once you've got it, play with it, enjoy it. A simple view from a genius. Terry Venables was an inspiration to me, and Alex Ferguson. It was a lovely rise and on the way back down the other side too, playing for my beloved West Ham who I'd supported as a kid. Portsmouth was great, and Colchester too, though it didn't end up so well. I enjoyed every minute."
Above all, those three astounding minutes in the Nou Camp in 1999 as United's two super-subs, Sheringham and Ole Gunnar Solskjaer, completed a historic Treble with their goals against Bayern Munich in what we should probably now call Fergie Time. If it seems ungallant to suggest to one of the heroes that United were fortunate to win, he admits to almost agreeing at the time. "But I watched it again on ESPN a little while ago and I didn't think we were as bad as people said and what I'd thought. I was quite pleasantly surprised, we had a lot of chances. The memories are very clear. I was like, 'Get me on, I'm ready, get me on', and the manager said, 'Go on and get yourself a goal, change this game for us'." Which, poker-faced, he did.
Teddy Sheringham played in the PokerStars European Poker Tour. For information, visit pokerstars.comReuse content