I don't doubt that many people like have seen the title of this entry and chuckled inwardly to themselves. The manager of the biggest club in the whole world, turning his back on his probable megasalary to take a sojourn at a little club in North London? Unlikely, it may initially seem. But it might in fact not even be Ancelotti's choice at all whether or not he's forced to reconsider his immediate career plans pretty soon; if Madrid lose the Champions League final, it's more than a possibility to Fiorentino Perez will cut the Damoclean cord on yet another hapless Real manager, and the Italian will be free to take on a fresh challenge right when we have a space opened up for him. Let's dare to dream, shall we?
Carlo Ancelotti, Real Madrid manager
Career Record: From the beginning of his managerial career with Reggiana to the time of writing, Ancelotti has overseen 907 games, presiding over 521 wins, 222 draws and 164 losses. That gives him a win percentage of 57.4%.
Accomplishments: Ancelotti boasts easily the strongest history of domestic and European trophy wins of all of the candidates that Daniel Levy can realistically approach this summer. Highlights include two Champions League wins (2003 and 2007) and the Serie A title (2004) with Milan, the Premier League and FA Cup with Chelsea (2010), Ligue 1 with PSG (2013) and the Copa del Ray with Real Madrid (2014). A proven winner on more or less every stage his sides have competed on.
Before he was a football manager: Ancelotti was a universally-renowned player who across his time with Parma, Roma and Milan racked up three Serie A titles and two European Cups. He was a key facet of the historically fantastic Milan side in the late 80s and early 90s that also boasted Paolo Maldini, Ruud Gullit, Frank Rijkaard and Robert Donadoni.
Tactical analysis: The genius of Carlo Ancelotti's tactical approach is that he doesn't really have an approach. Like Bruce Lee's 'style of no style', Ancelotti (presumably) sees a rigid tactical template as being akin to pointing a finger at the moon- remove the finger and you see the moon itself in all it's beauty, or something like that.
What I'm getting at is that Ancelotti has traditionally sought to draw the most strength from his sides by maximising the skills of the individuals he's given to work with. An ultra-adaptable type, he is prone to constantly tweaking and adjusting lineups and roles to accommodate his biggest stars, even if it means going outside the boundaries of what even the most radical of tacticians would consider comprehensible.
A classic case study can be drawn out of Ancelotti's highly successful five-year at Milan, where initially he started off arranging his side in a classic Italian diamond 4-4-2. With the signings of players such as Rui Costa and Kaka, Ancelotti continued to evolve this approach until it started to resemble more of a 4-3-2-1 Christmas tree, enabling four or five creative players to be fitted into the side at any given time. This gradual shift helped his Milan side to build towards their second CL title in 2007.
This pattern of adaption to reflect individual contribution and form has been repeated at every club Ancelotti has since managed. His spell at Chelsea began with him attempting to revive his diamond 4-4-2 formation, an approach seldom seen in the Premier League, before making a second-term switch to a more familiar 4-3-3. At PSG, he initially deployed his players in the Christmas tree that had served him well at Milan; by the end of his tenure, the side had transitioned to an almost outlandish 4-2-2-2. Most recently at Madrid, he has employed Angel Di Maria through the centre of a 4-3-3 to utilise his energy and bursting runs from deep while ensuring that the most expensive and second most expensive players in football history, Gareth Bale and Cristiano Ronaldo, can retain their preferred places on the flanks.
This guy sucks; why is he on the list?: If there is any sort of major reservation at all with Ancelotti, it's that he's only ever had fantastic players to work with at every club he's managed since his days at Parma. It's very easy, some might argue, to hold a super-fluid stance on tactics when you have individuals in your side capable of carrying your team through whole seasons and deep cup runs off their own backs.
That said, Ancelotti is far from the type of manager who leaves his teams to sort out the business of winning entirely on their own. His sides often show clear evidence of distinct and carefully-trained approaches when transitioning back and forth between defence and attack, illustrating obvious coaching nous on the part of the man directing them. Also, the obvious downside of having a squad of insanely talented individuals is the inevitable clashing of egos that comes with it; an issue that Ancelotti is famous for being excellent at mitigating with his laid-back, conciliatory approach. Great players alone don't win titles; it takes a great manager to get them all pulling in the same direction, and Carlo is something of a master shepherd in that respect.
Would he come to Tottenham?: In his own words, yes. At one point in time, at least. In the wake of being hired by PSG, he told Gazzetto del Sport that he had previously been hoping for a space on a 'top London bench' to open up, namedropping Tottenham specifically. Whether or not his recent spell in the most important hotseat of them all has cooled his interest in taking on the challenge of a more modest side like Tottenham, however, remains to be seen. Of course, this only matters if Madrid fire him.
Final thoughts: One of the defining figures of the past decade of European football; if there's even the slimmest chance that Ancelotti and his glorious eyebrow might one day grace the Lane, Daniel Levy has to grasp it with both hands.