After West Ham United won the FA Youth Cup in 1999, giving rise to the likes of Joe Cole, Frank Lampard, Rio Ferdinand and Michael Carrick, a teenage striker by the name of Jermain Defoe needed little convincing.
While initially making waves in Charlton Athletic’s academy, the future England international made a controversial switch across the capital when he was still only 16.
A fresh-faced Jermain Defoe had seen Carrick and Cole help West Ham lift the Youth Cup. Lampard was already a regular under Harry Redknapp by that point, while Ferdinand was starting to make his mark as well.
An easy decision, then.
By his own admission, though, the limelight which came as the result of his contentious move from The Valley to East London took him aback.
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West Ham United paid a compensation fee of £1.6 million for a 16-year-old striker.
The Hammers were also forced to deny making an ‘illegal’ approach, per The Guardian. Charlton’s managing director at the time, Peter Varney, hit out at their rivals’ approach, labelling West Ham a footballing ‘predator’ following a deal which left a very sour taste in Addicks’ mouths.
Jermain Defoe says the reaction to his West Ham United transfer was ‘mad’
Defoe would go on to score 41 goals in 105 games for West Ham, before finding the net for fun with the likes of Tottenham Hotspur, Portsmouth and Sunderland.
“I decided to go to West Ham because West Ham just won the FA Youth Cup,” Defoe told Suited and Booted TV. “They had Joe Cole, Michael Carrick, all that lot. Obviously, being from the East End as well, it was closer to my family. Some of my cousins were West Ham fans and a lot of the players I played with were my friends, from my district.
“I was 16. I actually think it’s mad, when I think about it now. A 16-year-old, [who had] just left school.

“When they paid £1.6 million, it was on the news, in the papers. I had to go to a tribunal. It was like this ‘wonderkid’, and all that. I hadn’t kicked a ball for the first team! I hadn’t even kicked a ball for the West Ham youth team.
“I remember my first game against Wimbledon, I came off the pitch and there were paps [paparazzi] taking pictures of me! I remember saying, “Why are some guys taking pictures?” Honestly, it was the maddest thing.
“You know what you’re like when you’re young: you’re fearless, playing football, this is what I do. But when I look back now, that was just mad.
“There was potential, but there were no guarantees [I would make the grade].”
Defoe idolised Paolo di Canio at Upton Park
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Defoe took a real liking to Paolo di Canio during his early days in claret and blue. The iconic Italian’s approach to training, in particular, was something that resonated with a teenager who had quickly come to understand the importance of professionalism and mature off-field conduct.
“I used to hear stories of the [youth team] boys going out drinking and I was like, ‘What? You want to be a footballer and you’re going out drinking? That’s mad’,” he recalls. “Me, I was home in bed by 9 just watching video tapes.
“All these things I used to hear, I was like, ‘It’s crazy, I can’t believe you’re doing that’. When I signed for West Ham, again I was like, ‘That’s the craziest thing, you’re not in the first team yet, why are you going out?’.
“I had that elite mentality at a young age and Lilleshall [the FA’s former School of Excellence] helped with the diet, how you sleep, how you recover, just being professional.”
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