The former England international recalls trying to force a move away from the club following the Hammers’ relegation from the Premier League
Defoe began his professional career at West Ham in 1999, and after a brief loan spell at Bournemouth, managed to establish himself as the club’s first-choice centre forward.
Unfortunately, the Hammers began to slip down the Premier League table in 2002-03, and were ultimately relegated after a 2-2 draw against Birmingham on the final day of the season.
Defoe handed in a transfer request less than 24 hours after that result, which the club rejected, and the striker was bombarded with criticism from supporters and experts alike for his disloyalty.
The former England international eventually apologised, but ended up joining Tottenham in February 2004 after a disappointing spell in the Championship.
“When I look back at it now, I think I was maybe naive at the time,” Defoe told Sky Sports while recalling his actions at West Ham.
“It felt like I was at school knocking on the headmaster’s door. If I saw someone do that now I’d be like, ‘Wow, that’s strange, you shouldn’t do that’.
“As a young player, you should never ask to leave the football club and hand in a transfer request. I didn’t even know about transfer requests then.
“I spoke to my agent at the time. He basically said to me and my family, this is something you need to do because you want to be playing in the Premier League and if you hand in a transfer request it gives you a better chance to leave the club.
“I should have turned around and asked more questions like, ‘Do I really need to do this?’ because if someone wanted me they’d come and get me.
“Of course it was a massive regret. It’s honesty from the heart, but I just didn’t know what I was doing at the time. I felt like I was on my own.
“All the stick that I got after was about me, not the agent or anyone else.
“In the paper is my face on a rat. Previous to that, everything in the back pages is of me scoring goals and it was all nice and good, but all of a sudden you’re dealing with this and it’s something completely different for me.”
Defoe, who now plies his trade in Scotland with Rangers, went on to reveal that he had the chance to join Juventus in 2009 after deciding to leave Portsmouth.
The 37-year-old opted to return to Tottenham for £15 million ($19m) rather than up sticks to Italy, but he admits to being flattered by the interest from one of the world’s biggest clubs at the time.
When asked how he reacted after being told by his agent that Juve were chasing his signature, Defoe replied: “I was like, ‘Wow, really?’ I was chuffed that a massive football club like Juventus wanted me.
“It’d be big going to a different league; I’ve always been confident and always felt like if I go there I’d go there and score goals.
“But I wanted to go back to Tottenham. I didn’t want to leave there in the first place, so of course, I want to go back home.”