The Hammers got relegated at the end of the 2002-03 season, and the forward submitted a transfer request the next day.
However, the club turned it down, but he refused to sign an extension and eventually joined Tottenham Hotspur the following January.
Defoe has since gone on to establish himself as a Premier League striking legend, scoring a total of 162 goals in 496 games and playing for the likes of Portsmouth, Sunderland and Bournemouth.
It’s been more than 16 years since he walked away from West Ham, but the Englishman remains apologetic for forcing an exit.
“I felt like I was betraying a family member. These people had given me an opportunity, and then years later I’m going in and handing in a transfer request saying, ‘I don’t want to be here, I want to leave’,”Defoe told Sky Sports.
“I made a big mistake. When I done it and realised what had happened, I felt like I had to get my head down and try to win the fans back.”
“When I look back at it now, I think I was maybe naïve at the time (when I handed in the transfer request). 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’.”
The 37-year-old is currently with Scottish Premiership giants Rangers and has scored 25 goals in 52 games.
He remains without a league title, with the Football League Cup he won at Spurs in 2008 the only silverware to his name.
It remains to be seen if he will end his career with a major trophy, but he has a chance at Ibrox, and it will be interesting to see if the former Hammers striker can end his career on a high note.
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