The best managers of all time: #12 - Carlo Ancelotti

‘People say that I was a banner for AC Milan. If that’s true, then he was the wind that made me flutter.’ – Paolo Maldini

Carlo Ancelotti is one of the most distinguished and accomplished gentlemen in football. The players that have worked with him can only sing his praises, and it is clear in the footballing world that he is a manager that footballers hold immense affection for. In the fast-paced times we live in, with players and managers constantly shuttling clubs this quality of the Italian can’t be lauded enough, and it takes a highly intelligent man to have stamped his authority on the number of clubs Ancelotti has in his career.

"He's like a big teddy bear, he's really sensitive and is a great guy, He's a great person and my only wish is that every player gets the chance to work with him because he's such a great guy and a fantastic coach. I miss him a lot. I want to work with him again” Cristiano Ronaldo said of Ancelotti some time ago, for instance, is another reflection of how much his former players love him.

But how does Ancelotti manage to so seamlessly integrate himself in his players’ hearts and minds, and get consistent results at the biggest clubs in the world so effortlessly? He hasn’t just walked into the footballing management world like that, but he’s earned and carefully developed each one of the qualities that make him so unique.

Ancelotti’s playing career

Ancelotti had a great playing career with Milan as well

Ancelotti started off at Parma, and would play in a much more offensive role than he would later make a name for himself in. Deployed behind the strikers under Cesare Maldini at Parma, Ancelotti made a name for himself in the lower rungs of Italian football before moving on to Roma where he was then deployed as a central midfielder. It was in this position where he would now begin to establish a legacy in.

His first dalliance with European success would come with the Romans, making the European Cup final in 1984 only to miss the showdown with Liverpool because of injury in a match that Roma would lose.

Arrigo Sacchi would lure the Reggiolo native to Milan then, in a trophy-laden era for the storied Italian club. Ancelotti would become an integral part in one of the best club sides of all time, the last team to successfully retain the European Cup trophy in the 1989-90 season after winning the trophy the year before. He’d have 3 Serie A titles and another 9 club trophies in his collection before he retired as well.

Entry to coaching and Tenure at Milan

Consistent with his brilliant playing career, Ancelotti had worked under some of the best managers in world football and his experiences with Arrigo Sacchi would perhaps be the most important. The revolutionary Sacchi would take Ancelotti under his wing and encourage him to become a manager. Ancelotti would then accompany Sacchi to the 1994 Fifa World Cup in which Italy reached the final and benefit massively from being by the brilliant managers side.

Ancelotti would have mixed spells at Parma and Juventus before he would come back to Milan to be a part of another trophy-laden spell with the Rossoneri. Ancelotti would guide Milan to 3 Champions League finals in 5 years with his famous diamond formation. His Milan sides would be a mix of a gorgeous array of technique in midfield and potency up front and they were a delight to watch.

Successful spells with Chelsea, PSG and La Decima with Real Madrid

Roman Abramovich had courted Ancelotti for years before finally getting his man in 2009. The Italian would immediately pick up a League and FA Cup title in his first year, thrilling Chelsea fans. Strangely, Ancelotti would be let go by the London club after finishing in 2^nd place the next year.

For the brilliant career Ancelotti has, it’s surprising to note how he’s been ousted from some clubs that he performed so well at in unimpressive ways. Ancelotti would depart from Chelsea after just a 2-year spell, but his win percentage with The Blues would be the third-highest in Premier League history

A Ligue 1 title with PSG would follow before Real Madrid came calling and Ancelotti would pack his bags for Spanish shores. Ancelotti would switch from a 4-2-3-1 to a 4-3-3 with Gareth Bale and Cristiano Ronaldo on the flanks, and Angel Di Maria in midfield (The last tweak would go on to be pivotal).

Madrid were simply desperate to win their 10^th Champions League title, a trophy they hadn’t won for 12 years. Ancelotti would deliver them that trophy in spectacular style, thumping Bayern Munich 5-0 on aggregate in the semi-finals and then overpowering their city rivals Atletico in extra time in the final.

Unfortunately, Real Madrid remain a club side with too much politics and powerplay in the boardroom, and they would relieve Ancelotti of his duties after the next season. He’d choose to turn down an offer to return to Milan and spend some time away from the game then, before recently taking up the reigns of Bayern Munich.

It’s easy to imagine Ancelotti winning another Champions League title with Bayern, he has the squad and the managerial skillset to instill the calm and poise it would take for the German giants to go all the way. Even if he doesn’t, the 57 year old Italian has stamped and charmed his managerial prowess in the annals of football history and will be remembered for generations to come.