2012: Adebayor says he's happy to be back at Spurs
Arsenal sold Adebayor to Manchester City nine years ago after the Togo international had burned his bridges in north London.
However, speaking to journalist Gianluca Di Marzio, Adebayor has now revealed he nearly joined AC Milan the previous year.
“Milan, I was close in 2008. I would have liked to play with legends like Kaka, Pirlo, Maldini and be coached by Ancelotti, but I did not do anything about it, but I stayed at Arsenal where I was fine,” he said.
Adebayor is now regarded as an Arsenal villain due to a match between the Gunners and City that took place months after his departure.
The Togo international had quit the north London club after fans had vented at him for flirting with a move away the previous year.
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Arsenal transfer news: Emmanuel Adebayor nearly didn't go to Manchester City
Adebayor scored for City against Arsenal at the Etihad Stadium and ran the full length of the pitch to goad the Gunners support.
And, speaking earlier this year, he explained why he celebrated as exuberantly as he did.
"A prisoner is out. A prisoner is free,” he said.
"I play for the club for three and a half years. They bought me for three or four million, they sold me for £27m, and they are still calling me names. They are still telling me I leave for money.
"You bought me for £3m, I still have five years' contract and you let me go for £20m more and you are telling me I am the one leaving for money and you are abusing me.
Moment Adebayor catches up with a SPRINTING Jeremain Lens
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"You can insult me no problem, but telling me my father washes elephants? I ain't taking that.
"So for me, it's just to show them that the person you are insulting still has something in his locker.”
Adebayor also told Di Marzio that, at the end of his career, he wants to return to his homeland.
“At the end of my career, I want to go back to Togo, I want to open schools and academies for the guys who deserve an opportunity, Africa is a wonderful place, but there is so much to do to improve it,” he added.
“Nowadays football is a wonderful dream to cultivate, but it's hard to make it, you have to study and realize yourself as doctors and lawyers, I want to transmit this to the boys.”