To understand how good Carlo Ancelotti is as a club manager, look at what he does NOT do…

The first time I saw a Carlo Ancelotti team in the flesh was at the atrocious 2003 Champions League final.

To appreciate what that game was like, imagine booking a five-star hotel and then flying out on holiday, only to find the place is still a building site. The saving grace was that it did end eventually, in Ancelotti’s favour.

I think about it now and again, though, because of how stacked the pitch was.

Old Trafford, home of Manchester United, was invaded by the heavyweight division of Italian football: Alessandro Nesta, Filippo Inzaghi, Andrea Pirlo and Paolo Maldini, a mere four names in the Milan line-up that Ancelotti went with. Opponents Juventus had Alessandro Del Piero, Gianluigi Buffon and Gianluca Zambrotta. I marvel at the travesty of all that pedigree grinding to a goalless draw over 120 minutes and a Milan win on penalties.

Putting the spectacle aside, that final shows how Ancelotti has been moving in circles of coaching excellence for so many years.

It’s impressive how much history the sport’s coolest cigar-smoker is associated with.

Maldini, his captain that night at Old Trafford, made his professional debut in 1985. Jude Bellingham, who Ancelotti signed to Real Madrid two years ago, is still just 21, so could easily play beyond 2040. The game is never too young or too old for Ancelotti and even today, at 65, it hasn’t left him behind. Things change, trends come and go, but Don Carlo sticks around.

Or he has to this point, in his 11th coaching job. But in leaving Madrid this summer, Ancelotti may be closing the book on his run in elite club management.

Don’t take that as read, because there’s something about him that brings European offers to his door — he’s rarely a bad answer to questions in high-level boardrooms — but by signing a contract with the Brazil national team, and starting work this month, it feels a little like Ancelotti is checking out. And with that in mind, the time is right to give some thought to where he sits in the pantheon of outstanding managers.

Historically, Ancelotti is one of the most interesting people in his profession — not based on what he is, but what he isn’t.

Unlike several of his peers, he didn’t create a movement. There is no School of Ancelotti and no wave of disciples behind him. He wasn’t the founding father of tiki-taka or the architect of Total Football. He wasn’t defined by gegenpressing, and he didn’t perfect the parking of the bus like Jose Mourinho did.

You could make a case for Ancelotti being the greatest club manager of all time, yet people rarely do.

Is it possible to define what the archetypal Ancelotti side actually looks like?

The very best coaches can seem tortured by the pursuit of purity or stylistic excellence. It’s why you see Pep Guardiola with self-inflicted scratches on his face. It’s why Jurgen Klopp bowed to fatigue and left Liverpool last year. You’ll spot the signs of constant stress oozing from Marcelo Bielsa.

Part of Ancelotti’s philosophy, or so it seems, is to be philosophical about his work; to avoid getting in too deep, psychologically.

He played for Arrigo Sacchi at Milan, but he doesn’t act like him. If you read The Immortals, Sacchi’s diary from his reign at Milan, you’ll discover an inspired eccentric who treated coaching like a science project. Sacchi was recommending thermal mud baths to players in the mid-1980s. To pinch Klopp’s quote from the front cover of that book: “Sacchi completely changed how we think about football.”

That won’t be said about Ancelotti. But does it matter?

Here’s the counter-argument: Ancelotti, as a coach, has won 30 trophies (admittedly short of Guardiola, who is knocking on the door of 40). He has claimed the title in all five of Europe’s big leagues — the Premier League, La Liga in Spain, Serie A in Italy, Germany’s Bundesliga and Ligue 1 in France — and combined with his five successes in the Champions League, this represents the full set. Nobody other than him has done it. He is also out on his own with those five European titles, ranging from 2003 (let’s not speak of it again) to 2024.

That’s the tail-end of the analogue era, running right through to the current height of the digital age. If football thought Ancelotti would become outdated someday, it was very wrong.

Objectively, his CV is a list of big teams and big budgets. He was supposed to shoot high with these clubs, but confidence in his manner and professionalism explains why he was entrusted to lead them in the first place.

A conclusion you can draw from his durability at the top is that footballers can connect with Ancelotti. That was true in the early 2000s, and it’s still true 20 years later. To stay the course requires a human touch.

Tactically, he gives the impression of a coach who will bend to accommodate the strengths of any given squad, rather than insist on a set of players suited to dogmatic principles. It doesn’t always work and Madrid have run off the tracks this season. But the shuffle of his midfield on the way to a double of trophies in La Liga and the Champions League last season was the mark of a man who understands his craft.

So, is there a way of working out where Ancelotti ranks in the pantheon?

Reducing the Italian to data is regrettable because it strips away the style of a man who poses with cigars at trophy parades and blows casually on his touchline cups of coffee as goals fly in for the team he is managing. He would probably prefer not to be painted by numbers. All the same, how can you accurately gauge whether Ancelotti, as a full package, pips Guardiola or Sacchi or, going back further, a genius such as Johan Cruyff?

Aurel Nazmiu, a senior data scientist with analytical firm Twenty First Group, did his best to provide a modern-day verdict.

Using a metric based on the wage bills of respective clubs, he calculated that in the period from the 2013-14 season to the 2023-24 one, Ancelotti’s three Champions League wins with Madrid were roughly two more than expected. It registers him as the leading overperformer in that competition (Guardiola is the biggest overachiever as a whole, with 18 major trophies at Bayern Munich and Manchester City, 10 more than the stats predicted he would win).

Domestically, Ancelotti’s three league titles in the period concerned fall short of the 4.5 anticipated by Aurel’s model but a total of eight major trophies is bang on target. The Italian delivers, and nowhere more so than in the Champions League, a stage where Guardiola has often been driven to distraction.

Maybe that’s the most pertinent contrast.

There are coaches whose teams you’ve enjoyed watching more — if you’re reading, Carlo, I’ll accept cash or card by way of a refund for those couple of hours at Old Trafford — but Ancelotti’s club career hasn’t been that of a manager seeking validation. He’s no pussycat, and surviving for four years straight in his second spell at the Bernabeu doesn’t happen without a set of teeth or a degree in diplomacy, but it isn’t his style to go rogue or deflect blame, nor does he have to be the darling of the sport.

Though football can leave the finest coaches looking drawn, battered and empty, Ancelotti has the air of one who told himself to enjoy it until the music stops.

He’ll have regrets, of that there’s no doubt. But unlike some of his contemporaries, I’m not sure they’ll keep him awake at night.

(Top photo: Ancelotti and his captain, Paolo Maldini, arrive home in Milan with the Champions League trophy in 2003; Giuseppe Cacace/Getty Images)

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