The Togolese striker has fallen out with a number of his managers in the past but has found a new lease of life under Tim Sherwood and is leading Spurs' Champions League charge.
He decided to jump in his car and head down to Leicester, where Real Madrid was playing a friendly at the King Power stadium. The striker had just spent six months on loan at the Santiago Bernabeu, where he scored eight goals in 22 appearances, just nine of which were starts.
|BACK IN BUSINESS
|ADEBAYOR'S LAST THREE SEASONS
|GOALS PER GAME
No doubt, part of that discussion would have involved Adebayor begging for Madrid to sign him - and if you listen to the Togolese, the move was only prevented by internal politics at the Spanish club.
Shortly after completing his initial loan spell to Spurs in 2011, Adebayor said: "Politically, it is always difficult. There is not just one man deciding. If it was just Mourinho, for sure I would be in Madrid now.
"We have been in contact throughout all the holidays and he gave me the go ahead to go to Tottenham and I am very happy to be here today."
As Mourinho prepares to face Tottenham on Saturday teatime, much of his pre-match thinking will revolve around how Chelsea can stop Adebayor and boost the club's Premier League title prospects.
Adebayor has been in remarkable form since being welcomed back from the cold by Tim Sherwood in mid-December following the dismissal of Andre Villas-Boas. The 30-year-old has scored eight goals in 12 league appearances under Sherwood and provided three assists.
From training with the youth team, Adebayor has become the most important player in the side and one of the leaders of the dressing room at White Hart Lane. He is almost single-handedly carrying Tottenham at the moment, and is directly responsible for more goals under Sherwood (54 percent) than Gareth Bale under Villas-Boas (38 percent) or even Luis Suarez for Liverpool this season (46 percent).
The general perception of Adebayor is that he is more of a liability than an asset, unpredictable and impossible to control or manage.
But is that really the case? Or has he just been horrendously mismanaged at points in his career?
Last week, after scoring twice against Dnipro to fire Spurs to the last 16 of the Europa League, Adebayor said: "I want to say a big thanks for the new gaffer, who came in and gave me my confidence back, gave me the stage to play on."
Confidence. That’s all it comes down to with Adebayor - make him feel empowered, tell him he’s special, massage the ego and you can bring out the best in one of the most talented strikers in the league.
"I would say Harry is similar to Mourinho because of the way he treats players and gives you confidence," Adebayor once said.
"That sensation when Mourinho said: 'Adebayor we know you are creative, we know what you can do on the football pitch' and he said 'go out there and enjoy yourself - I cannot tell you go left or go round because you know what to do on the football pitch.'”
Sherwood has taken a similar stance - the arm around the shoulder, make him feel important.
With Villas-Boas there was a clash of both egos and personalities, and the end result was that Adebayor scored just eight goals last season before he clashed with the Portuguese during preseason and found himself training with the youth team.
Villas-Boas, like Roberto Mancini at City, simply refused to indulge Adebayor. In the end, the Portuguese’s treatment of the forward was one of the reasons he lost his job following a humiliating 5-0 defeat to Liverpool in December.
Of course, Adebayor is no angel. After scoring 30 goals for Arsenal in 2007-08, he fell out with the club the following season over a new contract and was sold to City in July 2009.
He frustrated Wenger with his attitude while he also had a poor relationship with his strike partner Robin van Persie.
Adebayor has never attempted to hide his attraction to money - much of which is reinvested in charities back in Togo - to the extent that he even threatened to sit out his contract at City before completing a permanent switch to Spurs in 2012.
He is Tottenham’s highest earner, the only man in the squad on more than 100,000 pounds-a-week, but in the last two-and-a-half months, at least, he has delivered the results. He is paid for goals and under the right manager that’s exactly what he will produce
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