As a professional at Milan he was one of a legendary, multiple European Cup winning team that is still widely regarded as one of the best club-sides ever. His career at Roma before that was a success too. He is one of only a handful of players to have won the European Cup as player and coach.
As coach of AC Milan he won only one Scudetto in 2004, but many domestic cups and two Champions Leagues (2003, 2007) while making the final of a third (2005).
At Chelsea in 2010 he became the second non-British coach to win the double with Chelsea. He was sacked when Chelsea lost the league the following year in 2011.
At PSG success has been mixed. When he arrived in late 2011 PSG were leading Ligue 1. A few days later PSG were knocked out of the cup by Lyon. That was followed by a terrible run of form in the league which meant the team ultimately won nothing, coming in second to little-team-that-could Montpellier.
One expensive summer later and Ancelotti is now heading up a star-studded dressing room with his team about to win their league. They did well in the Champions League, only losing the quarter finals on away goals to Barcelona.
Ancelotti is a coach who has handled great players and big dressing-room personalities well – possibly because he was a great player himself. At Chelsea, in a dressing room that hounded out his successor, he was not only an authority but well-liked. At PSG – a United Nations of talent and players cobbled together – he is a diplomat, getting on well with what sounds like a demanding owner.
His time as a player has made him sensitive to the pressures players feel. "I was a player myself so I understand how a player can make mistakes, I made many..." In a fascinating series of mini-lectures provided to Four-Four-Two he expanded on his methods of helping players get out of form dips or recover from bad games. The approach is very personal and empathetic. Ancelotti avoids berating a player in public or in a group.
He is affable and easy to get along with - leaving England with a positive reputation among the press as a diplomatic man.
Ancelotti is tactically astute but not an innovator. He is a cup-tie specialist. He does not impose a style, precisely. One cannot speak of a "typical Ancelotti team". For all that, he is very fond of tactics – the sort of coach who spends his time working out the mysteries of the perfect counter-attack.
His Milan were an amazing collection of players for many successive years in the Champions League, well-organized and disciplined and successful, while falling short in the league. His Chelsea (already a successful side when he arrived) played much the same way – good players, who were well-instructed both in how they should play and how the opposition would play. He is a coach who trusts his players.
His time at PSG is harder to judge. Ligue 1 is not a technical league and he has an eclectic, not always sensibly chosen squad in a league of minnows.
In the Champions League this year his team was competent, and could even be said to have overachieved.
Experience at the largest clubs in Europe
Non-fractious relationships with difficult owners
Experience in several leagues and with players of every culture and background
Considerable cup success – in Europe and domestically
League wins in Italy, England and (shortly) in France
A somewhat weaker league record when compared to his cup record.
The man who prevented Ancelotti making it 3 wins from 3 European Cup final appearances is Benítez, who won the European Cup in 2005 with Liverpool.
Benítez is a Real Madrid youth product – born in Madrid, playing for the club’s youth teams. He also worked, briefly, on Madrid’s staff before coaching unsuccessfully elsewhere in the league. Then he led Valencia to a league title in 2000-2001 and again in 2003-2004 (when he also won the UEFA cup).
Significant domestic success never came for Benítez at Liverpool. His team made another final in 2007 – this time losing to Ancelotti’s Milan in a mirror-fixture to 2005. In 2008 the team (again, arguably, overachieving) made the semifinals of the competition.
A brief and comical tenure at Inter led to a two year hiatus before he arrived back in England to take over Chelsea as "interim manager" after Roberto di Matteo was sacked. His players, the fans and his club are all waiting him out to varying degrees of impatience.
Benítez’s man management is interesting and as uneven as his coaching career. He was intelligent and proactive enough to split up a clique of 4 English players at Liverpool upon his arrival (selling off two and keeping Gerrard and Carragher) because he could see they had too much influence. But his time at Liverpool was marked by aggressive transfer policies that seemed deliberately designed to unsettle players. While complacency should be discouraged, one can take it too far. His players at Liverpool - Jerzy Dudek and Xabi Alonso among them – were often unhappy under him, with Dudek relegated to the bench the season after his heroics in the Champions League and Alonso leaving for Real Madrid. He is a distant coach.
His brief spell at Inter had his players (fresh from winning the European Cup with Mourinho) in an uproar. There is no sense he was liked or respected by that team. His time at Chelsea has an element of extreme farce about it, with the insulting title of "interim" manager and the fans eager to hound him out of the Bridge.
His relationships with those upstairs have been fractious too. At Valencia he fell out with the management over transfers. He did the same at Liverpool, with the owners desperate to see the back of him by the time he left. At Inter he was quickly sacked by a Massimo Moratti who had no interest in an overly-aggressive transfer policy either. Inter’s appalling league position only months after their treble was another factor. At Chelsea he was widely expected to be sacked in February after berating the fans and criticizing his work-title.
Chelsea, unable to replace him, finally backed him up - for the interim.
There’s nothing particularly interesting about a Benítez team – one cannot speak of a "system" as he is, like Ancelotti, no great innovator. But he has a situational intelligence that makes him very adept at changing tactics mid-game, most famously in the 2005 final against AC Milan with his team down 0-3 (though one player was forced to point out they needed 12 men on the pitch to implement his plans). This can lead to substitutions mid-game that are inspired (when they work) or come off as slightly odd (when they don't).
Commentators speak, a little lazily, of a defensive style. He is certainly a coach who wants his teams to be solid in the back.
He is also a zonal marking proponent, leaving his teams, or so the received wisdom would have it, apt to concede on set-pieces. He rotates, constantly (even excessively), which could account in part for how well, comparatively, his Liverpool did in the later stages of the Champions League while not really impressing domestically.
Benítez does not, therefore impose a personal style. While Chelsea now plays a slightly less expansive game than under di Matteo earlier in the season and are struggling to keep a Champions League spot, they are still a vastly different team from his Liverpool – a team that did sometimes love a long ball and in which Pepe occasionally got an assist.
Benítez takes no interest in youth development. No youth players were promoted during his tenure at Liverpool.
Some considerable domestic success in Spain.
A tenure at Liverpool marked by over-achievement in the Champions League.
Tactical acumen, the ability to react.
An uneven managerial career.
Limited interest in youth development.
Known issues with players and management.
Teams prone to conceding on set-pieces.
A policy of excessive rotation.
Which do you prefer?