But a reunion with Harry Redknapp at White Hart Lane proved the reason why the striker didn’t complete a switch to the Italian giants.
Defoe moved to the Blues from Spurs for a fee of around £7.5m in January 2008.
The England international proved an instant hit, netting eight goals in 12 appearances to ensure Pompey qualified for the Uefa Cup the following season.
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However, then-boss Redknapp would quit the Fratton Park hot seat in October 2008 – only months after guiding the Blues to FA Cup glory – to take charge at Tottenham.
And much to the ire of Pompey fans, Defoe would make the same move when the January transfer window opened.
The current Rangers man, however, told that he got a surprise call from an agent who offered him the chance to instead donned the famous black and white stripes of Juventus.
Speaking to Sky Sports, Defoe said: ‘That’s the first thing I thought (about reuniting with Redknapp after he left).
‘And that's not even me being disrespectful to Portsmouth, but I think naturally anyone in my position is going to think, if Harry's brought me here and he's gone to Tottenham then of course he's going to want to bring me back. It makes sense.
‘I suppose I was just waiting for the phone call.
‘Juventus want you (the agent said), so if the Tottenham thing doesn't happen I'm taking you to Juve because they're really interested and they want you to go there.
‘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.
‘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.
‘Maybe Daniel Levy (Tottenham's chairman) got the phone call about Juve, because straight after that the deal was done. I felt happy again.’
Nevertheless, Defoe had no hesitations moving to the south coast in the first place.
He said: ‘You know what Harry's like. He said “JD, do you want to come and play here and get your goals?” and I was like “Yeah, no problem gaffer”.
‘If I was going to go anywhere, I’d want to go and play for Harry again.’