Several years ago, Carlo Ancelotti was asked a question. How many Champions Leagues can you win, Carlo? No, it wasn't that. Will you go down as one of the greatest, Carlo? It wasn't that either.
Instead, the illustrious Italian manager was asked: "Why have you decided to release Luke Garbutt?"
It feels like a parallel universe, doesn't it? In classic fashion, Ancelotti raised an eyebrow before replying "who?" It really was press conference cinema.
At the time, he was managing Everton, a moment in his rather incredible career that will probably fall towards the bottom of his achievements. No disrespect to the Toffees, but it does defy belief that they were able to entice him to Goodison Park.
In the four years since that remarkable moment, Ancelotti has cemented himself as one of the greatest tacticians to have ever lived.
On a brisk Sunday evening at the beginning of June, he took home a fifth Champions League trophy and his second since leaving Merseyside behind, cementing Real Madrid's legacy even further.
This time it was achieved under the famous arch at Wembley Stadium. Madrid took longer than they had hoped to break the deadlock, but after Dani Carvajal headed home, it all began to feel rather inevitable.
Vinicius Junior soon scored to make it 2-0. "Ballon d'Or, Ballon d'Or," Rio Ferdinand shouted. Quite. The Brazilian should well be in the conversation.
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However, we're not here to discuss that, we're here to discuss the greatest manager of all time, a debate Ancelotti more than deserves to be mentioned in. So, what are his credentials?
The most successful managers in the Champions League
The 64-year-old has a great love affair with Europe's premier competition, winning the title now on five occasions.
The first of those titles came with AC Milan in 2002/03 before the Italian giants were crowned continental winners again in 2006/07.
The veteran had to wait until 2014 to take the crown home once more, winning the first of three Champions Leagues with Real.
Back for a second spell in Spain's capital, he won it again in 2021/22, a season after leaving Everton – and then rounded off a handful of triumphs in 2024.
So where does that place him among the best to do it in the competition? Well, he's right at the very top. No manager has won more Champions League trophies than Don Carlo. In fact, he's now two clear of some pretty illustrious names.
Rank
Manager
Titles
Years won
Club(s)
1
Carlo Ancelotti
5
03, 07, 14, 22, 24
Milan, Real Madrid
2=
Bob Paisley
3
77, 78, 81
Liverpool
2=
Zinedine Zidane
3
16, 17, 18
Real Madrid
2=
Pep Guardiola
3
09, 11, 23
Barcelona, Man City
16 have won it 2x, including Mourinho, Ferguson, Del Bosque & Clough.
So, as far as Champions League success is concerned, there is no one more decorated than the current Madrid boss.
But what about when it comes to overall trophy wins, who reigns supreme there?
The most successful managers of all time
Ancelotti's haul of five European trophies is a rather remarkable tally, but he's not just a one-trick pony.
The former Chelsea boss has achieved some pretty impressive accomplishments domestically, too, notably winning all of Europe's big five leagues – the only manager to record such a feat. His first came in 2003/04 when he guided Milan to the Serie A title.
He then won the Premier League with Chelsea in 2009/10 before guiding PSG to Ligue 1 glory in 2012/13. A Bundesliga title at Bayern Munich was forthcoming in 2016/17 and he is now also the proud winner of two La Liga titles with Real, winning the trophy in 2021/22 and 2023/24.
Throw in a bucket load of cup victories and it means that as of June 2024, Ancelotti has won 29 major honours, the fifth-most of any football manager in history.
Who comes out on top? It'll be no surprise to see Sir Alex Ferguson sit at the summit of the list with a staggering 49 trophies throughout a decorated 39-year career in management.
Rank
Manager
Trophies
Years Active
1
Sir Alex Ferguson
49
1974-2013
2
Pep Guardiola
39
2007-present
3
Mircea Lucescu
38
1979-2023
4
Valeriy Lobanovskyi
30
1969-2001
5
Carlo Ancelotti
29
1995-present
6=
Jose Mourinho
26
2000-present
6=
Luiz Felipe Scolari
26
1982-present
6=
Jock Stein
26
1960-1985
6=
Ottmar Hitzfeld
26
1983-2014
7
Giovanni Trapattoni
23
1972-2013
Considering Ancelotti's age, it's highly unlikely he'll get anywhere near the 49 won by Sir Alex, but providing Pep Guardiola can't inspire anything further with Man City in the next few years, he will hold onto that incredible Champions League record for a little while longer.
Celebrated as "an unbelievable person" by Cristiano Ronaldo, as "a second father" by Alessandro Nesta and as a "world-class" coach by Jude Bellingham, he is a manager to have gained praise from some of the greatest we've seen in the game.
He's achieved things no other manager has ever done and deserves to go down as one of the best to ever stand in a technical area. It will be a sad day when that retirement announcement comes.
Still, he has a few more years to go. With Kylian Mbappe in tow from next season too, you wouldn't put it past Madrid to win a 16th Champions League and Ancelotti's sixth. Watch this space.
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