After more than two decades in professional football, the 39-year-old has called time on his career – despite penning a short-term deal with Sunderland only weeks ago.
The striker made an emotional return to the Black Cats on February 1, but after seven goalless appearances has ended his second spell on Wearside early.
Since making that call, Defoe has been reflecting on his career and explained his decision to retire to talkSPORT.
And in that interview, the former Blues front man revealed the two failed moves that still play on his mind.
The first – to Sir Alex Ferguson’s Manchester United dynasty.
And the second – to Juventus, when he was plotting his departure away from Fratton Park, after only a year on the south coast.
A transfer to Italy never came to fruition, as Defoe followed Harry Redknapp to Spurs instead – to the anger of the PO4 faithful.
However, the ex-England international explained he doesn’t dwell on what could have been.
Instead, he’s delighted with how his career panned out – which includes 324 goals from 819 appearances.
Speaking to Jim White and Simon Jordan, Defoe said: ‘I was always linked with Manchester United.
‘I remember speaking to some of the Manchester United boys years later and they thought I was coming to them.
‘Some of the lads said “what happened? We were told you were coming”.
‘At this stage now, I think that would have been amazing because playing for someone like Sir Alex Ferguson, with all the trophies they won!
‘At the same time, I try not to regret anything, really. It would have been great had it happened but things happen for a reason.
‘I remember getting a phone call from my agent when I was at Pompey, when I was going back to Tottenham.
‘The day before I signed for Spurs, I got a phone call from my agent saying “I’m taking you to Juventus, they want you”.
‘I think that would’ve been great playing for a club of that size and experiencing a new culture in Italy.
‘He asked me “would I like to sign for Juventus?” which I was wowed by, but I said “I wanted to go back to Tottenham”.
‘I went back to Tottenham and I loved it. Harry Redknapp signed me again.’
With seven matches remaining, Defoe’s last club, Sunderland, find themselves firmly in the the play-off race.
Alex Neil’s side currently occupy sixth place in the table.
Yet, despite promotion being a possibility, Defoe cited his struggle to play through the pain barrier as to why he’s unexpectedly retired.
He added, though, that a career in coaching would interest him.
‘I believe, for me, it’s the right time because as you get older it doesn’t get easier,’ said Defoe, who scored 17 goals in 36 appearances for Pompey.
‘Probably, the more time that goes on without really playing it becomes more difficult.
‘I didn’t really want to block the path of a youngster coming through, or someone coming back from injury.
‘Of course (I’d like to coach).I think a lot of coaching now is speaking to people, speaking to younger players about the game and I think I’ve always done that anyway.
‘To take it to the next level where I complete my badges would be great, because then if I have that you never know where it could take you.’
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