Who could have imagined the transformation in lifestyles? Not the bejewelled character with the laughing eyes seated opposite, who in his boyhood indulged in an apprenticeship for a career as a hoodlum on the mean streets of Zaandam, near Amsterdam, but who now enjoys the millionaire existence of a Harrogate gentleman. And not George Graham, the man principally responsible for coaxing the latent striking prowess from this adopted Englishman, when he learns that Jimmy Floyd Hasselbaink has designs on becoming a top coach.
At a moment when Sir Clive Woodward is priming himself for such a footballing move, that may not sound so preposterous. Except that the Dutchman has much loftier ambitions. "The idea of becoming an assistant coach to Guus Hiddink or Louis van Gaal when I stop playing still appeals to me," he writes at the conclusion of his newly published memoirs*; a decidedly cathartic exercise which begins with the assertion that it was football which saved him from, well, who knows what kind of villainy?
"Most likely I would have ended up like my friends, still doing the same things," says this powerful, prolific scorer when we meet at Middlesbrough's Rockcliffe Place training base. "There's a big chance I would have been more in trouble. Football definitely took me in the other direction."
The "same things"? Suffice to say that many of his comrades from those days in what he refers to as the Zaandam "Bronx" are drug dealers, addicts, or serving long prison sentences. Hasselbaink himself spent three months at a youth detention facility after his gang threatened people outside a rap concert and stole their tickets. He carried a knife at one time, but never a gun. That scared him.
Maybe he should volunteer to be part of a campaign to discourage youngsters from carrying knives? He appears slightly surprised by the question, but concurs with the reasoning behind it. "I would, if there was a campaign and they wanted my help. I more or less had the knife just to be cool back then. Because I was one of the group, you know? I had the wrong friends. I lived in the wrong area. There were a lot of junkies on the streets, people selling drugs, and there was violence. But I would never have used it, because I'm too big a coward for that."
His mother, Cornelli, lived in that neighbourhood until six years ago. "When I used to go back there and walk with her down the street, people I used to know would stop me and ask for stuff, like, 'Could you get me a [football] shirt?' Then you think back, and think how really fortunate you are. It doesn't matter that I became a footballer and that I'm a wealthy boy [one who sports diamond studs in his ears costing £15,000, in case you were wondering]. I'm just proud that I've left that life behind and become a better person."
He adds: "My best friend then, from age seven, Oswald Snip, is still my best friend. He became a professional footballer in Holland. We have never done drugs, we have never smoked hashish or weed, or whatever. OK, we had a drink, and got home drunk, but our life was always football - until this day."
Jerrel, as he was born, began his career with the Dutch teams Telstar and AZ Alkmaar, but by the age of 23 he had moved to Campomaiorense in Portugal, and become "Jimmy", by the order of that club's chairman for reasons best known to himself. It was to prove indelible as this nomad subsequently encamped at Boavista before finally arriving at Leeds, and an authoritarian figure by the name of George Graham, in the summer of 1997.
To suggest it was a love-hate relationship is painting far too romantic a picture. "We didn't have stars in our team," recalls Hasselbaink. "Only Lee Sharpe, and he didn't play. There were 11 of us more or less on the same level. But we were a really good team. We were hard to break down, and that was because of George Graham. He made us defend in a proper way, all 11 of us. He was very hard on me. He used to get on to me about everything; me not working hard, me not running in the channels. And yes, at times, I thought, 'Hell, he hates me. What does he want?' "
He smiles ruefully as he recalls one particular memory. "A defender had pushed me to the ground. George said, 'You're playing like a poof'." When it comes to football, I do have a temper [he once chased after Spain's Fernando Hierro, threatening him, after both had been sent off in an international in Seville]. But all I could say was, 'What is a poof?' I didn't understand what it meant. One of the players had to explain it to me." Hasselbaink, who has apparently rarely been ignored by female admirers, was not having any of that. " 'Am I fuck,' I told George."
Yet Hasselbaink readily concedes: "In those early years, I needed someone to be hard on me. George was, really hard. It was not always fair, but it made you realise that you had to play well every match. And that's why we did well as a team. It's only afterwards, as you get older, and he's gone, and you experience other managers, you knew George was right."
Which brings us tangentially to the Dutchman's current manager, Steve McClaren. Is he resourceful enough to survive the perils of managing diverse England egos, should the biggest job of them all materialise? "The bigger the players, the tougher he will get," says Hasselbaink. "Yeah. He's been seen as a nice man, but he's been tough with me once or twice. I wouldn't want it any different. He's a very good coach and trainer. Very bright. He likes you to play football, likes you to pass. Obviously, he's still learning a lot in the game because he's still quite young. Will he be the next England manager? Well, probably not, because he's just signed a four-year deal here. But you never know."
Such are the vagaries of a sport in which Hasselbaink joined Chelsea when he had two years remaining on his Leeds contract, provoking accusations of disloyalty and greed. "Leeds were the club who put me on the map as a footballer. I acknowledge and appreciate that," he says. "But things were said that were just not true, and they made me out to be greedy. It hurt, and it was not right.
"[Leeds chairman] Peter Ridsdale just wanted to throw mud at me to make himself look good. Chelsea came in, made an offer to me. I told Leeds, 'If you are near to what Chelsea are offering I will stay'. Leeds said no. Am I a bad guy?"
He could not have known that he was joining the right club - the one for which he still harbours great affection - at the wrong time. He admits that when Stamford Bridge was a cauldron of euphoria in May after that first title had been secured in 50 years, "I didn't look". He pauses. "But I'm pleased for everyone I played with: Frank Lampard, John Terry [whom he maintains will be England's next captain], Eidur Gudjohnsen [his strike partner as well as his gambling accomplice during a period when Hasselbaink concedes he lost £100,000 at the tables]. Maybe if I had been a few years younger I'd still be there. I think I could have still brought something to Chelsea."
Particularly with Didier Drogba not immediately assim-ilating himself into the Blues' set-up? "What do I say? Drogba cost £24 million. In the first year, he didn't score more than I did - and I was playing at Middlesbrough." He shrugs. "But I never spoke to [Jose] Mourinho. [After Mourinho arrived] Peter Kenyon called my agent and just said, 'OK, we're going to let Jimmy go', and that was it."
You suggest to him that there may have been a personality clash. "I don't think I would have had a problem with Mourinho," he retorts. "When I speak to the [Chelsea] boys everybody says he is magnificent, even those not playing. So, he must be somebody special."
He adds: "I do feel at home here, and I'm part of something really nice. Obviously, there's a difference between winning something like that [the championship] and playing in the Uefa Cup. But I've learnt you can't have everything in this world. I regard myself as fortunate in a different way, just by becoming a footballer.
"Maybe to win all those things as well was a little bit too much for me. That's how I live with it."
Life & Times: From Zaandam to the Riverside
Born: 27 March 1972, Paramaribo, Surinam.
Vital stats: 5ft 10in, 13st 10lb.
Club career: Telstar 1990-91; AZ Alkmaar 1991-92; Campomaiorense 1992-96, 31 games, 12 goals; Boavista 1996-97, 19, 20; Leeds 1997-99 (signed for £2m), 84, 42; Atletico Madrid 1999-2000 (£12m), 34, 24; Chelsea 2000-04 (£15m), 156, 88; FA Cup winners 2002, Premiership runners-up 2004, European Cup semi-finals 2004; Middlesbrough 2004-current (free), 54, 20; Uefa Cup quarter-finals 2005. Total: 378 games, 206 goals (total fees £29m).
International career: 23 caps for Holland, 9 goals.Reuse content