Hail to the chief

No coach has experienced more Champions League success than four-time winner Carlo Ancelotti, the likeable Real Madrid boss proving that good guys can come first. And, as Paolo Menicucci discovers, he remains as warm, modest and hungry as ever

WORDS Graham Hunter

Interview
When you speak to Carlo Ancelotti, it’s impossible not get swept up in his infectious serenity and positive approach to life, two throwback qualities in the frantic world of modern football. And yet the Real Madrid coach is also a fascinating mix of progress as well as tradition, a 64-year-old eager to travel the globe and discover new things, but who will always consider his native village “the most beautiful place in the world”. A manager still dedicated to studying the latest tactical trends without ever forgetting the most important aspect of all, the human factor. In the words of his son and assistant coach Davide, “He’s a very affectionate person both at work and in his personal life.”

I first interviewed Ancelotti at Milanello, AC Milan’s training base, back in 2002. Already, he had come a long way since his youth in Reggiolo, the picturesque rural commune in Reggio Emilia known for its medieval fortress, annual pumpkin festival and – this will come as no surprise – the humble outlook of the locals. Milan were in the middle of their triumphant 2002/03 campaign, when Ancelotti led them to Champions League glory by beating his former side Juventus on penalties in the final. Our interview was scheduled for the morning, but we were later told we had to wait until the afternoon. While I was planning to get sandwiches for lunch with the rest of the crew, Ugo – a veteran of the Rossoneri press office and one of the nicest people I have met in football – came over and said the boss had invited us to eat with him and the team in their dining room.

It was my first season as reporter, and I was in my late 20s. I thanked them calmly and politely, but on the inside I was anything but calm, my head pounding with a single thought: “What???” I could hardly believe my eyes as I sat in the same room with Ancelotti and the entire team. The conversation was easy, the food was delicious, and occasionally the likes of Clarence Seedorf and Gennaro Gattuso would perch down and talk with Ancelotti about anything and everything. He did all he could to make us feel comfortable. He himself was completely at home at Milanello, of course. As a player, he had spent five seasons there, winning the European Cup twice among numerous trophies in the legendary team coached by Arrigo Sacchi. Now here he was in a different role, chatting and joking with the staff, from the chef to the cleaners, and all the while he was building one of the most spectacular sides in Europe.

When I meet with Ancelotti again at Madrid’s beautiful training ground, I cannot help noticing that not much has changed since we first crossed paths 21 years ago. True, I am also here to speak with Davide, one of his right-hand men as opposed to the 13-year-old boy he would have been then. And Carlo is carrying a few more grey hairs these days, but he is probably even fitter than he was at Milan – and his relaxed and humble approach remains the same. So too that famous eyebrow which arches suddenly when he tackles my questions.

Now a record four-time Champions League winner as a coach, Ancelotti would have every right to proclaim his opinions like a preacher from a pulpit, but instead he is as modest as he was before the first of those victories. “One key element is probably that I coached two clubs that care a great deal about this competition,” he says when asked the secret to his European triumphs. “It’s no coincidence that both Milan and Real Madrid are among the most successful clubs in the history of this competition, and this competition represents the most important trophy for both clubs. I don’t know what kind of mark I have left.”

Even so, I push him harder to open up about his huge personal contribution, reminding him of his key role in Madrid’s landmark tenth European title in 2013/14. “La Décima has your name all over it,” I tell him. “Yes, I mean, with Real Madrid I won two tournaments that will go down in history: La Décima and the 14th title, which were both inspired and inspirational at the same time.”

Well, it was worth a try. And, besides, we all know how crucial his influence was. Indeed, less than two years on from the second of those continental crowns, in 2021/22, his hunger is undiminished. “What helps me stay on top of my game is the passion I have for this sport,” he says. “I had it when I started playing as a kid, and I still have it today. It’s a very strong passion which luckily did not turn into an obsession. When you become a coach, you risk turning your passion into obsession. Football remains a great passion for me. When I have some free time and there’s a football game on, I’ll watch it, but I really enjoy films too. I love being with my family, my children, my grandchildren and my wife.”

That emphasis on personal relationships has undoubtedly helped him build strong bonds in every team he has overseen. You’d be hard pressed to hear any negative comments from his former players, a long list which includes some of the best footballers in the history of the game.

“Respecting the footballer is fine, but it’s much more important to respect the person behind the footballer”
Carlo Ancelotti celebrates the first of his two Champions League triumphs with Real Madrid, against rivals Atlético in Lisbon in 2014

“Respecting the footballer is fine, but I think it’s much more important to respect the person behind the footballer,” Ancelotti explains. “That’s my general approach. I’m not just a football coach, I’m a person who works as a coach. My own character was moulded by growing up with the people I consider my mentors, starting with my parents, and also my teachers and coaches. I always carry myself with the footballers I work with by focusing on them as people first and foremost.”

If anyone could query that assessment, it would be Davide, his son and assistant at the Santiago Bernabéu. Quite the opposite, in fact. “Both as a father and as a coach, he’s able to be authentic, to be himself, which means someone who cares a lot about his family members and his children,” he tells us. “The same goes for the players: he’s a very affectionate person both at work and in his personal life. He’s a very quiet person and there are never many conflicts with him. As a coach and as a father, he’s able to maintain a peaceful environment, the same as the one I grew up in when I was little. Objectively, there are very few differences between the father and the coach. I would say that the differences are almost non-existent. That’s why many players say they had a father-son relationship with him.”

A former footballer who played in the Milan youth system, Davide hung up his boots in 2009 when he was only 20 to pursue a career in management. He completed a Sports Science degree in 2011 and one year later started to work with his father as fitness coach at Paris Saint-Germain. He followed Carlo to Madrid, where he met his partner Ana, and in 2016 he received a UEFA A licence. Now 34, his eyes light up when he talks about his father, and their hug after Madrid’s incredible comeback against Manchester City in the 2021/22 Champions League semi-finals – on the anniversary of his late mother’s birthday – will always remain one of the most touching moments of that memorable campaign.

“I don’t remember when he was a footballer because he retired when I was four, but I recall we had this videotape at home with all his goals,” says Davide. “It wasn’t long as he didn’t score many, so I remembered them all. After watching it, I knew all those goals by heart. Naturally, I have more memories from when he became a coach. I remember being a very shy kid and, after the games, he would ask me to come back with the team on the coach, but I was so embarrassed that I couldn’t. I used to cry because I actually wanted to go, but I would say no in the moment because I was afraid of being there with Zinédine Zidane and Alessandro Del Piero, who were my idols. He would say, ‘Are you sure? You’ll regret it!’ That’s a memory I have from when he coached Juventus and I was a kid of eight.”

Ancelotti’s warm personality does not tell the full story, however. His flexibility and eagerness to study the latest football tactics have always been valuable attributes. He was a 4-4-2 fanatic early in his career, so much so that he famously refused to have a certain Roberto Baggio in his team because the Italy great did not fit into his system. A few years later, Ancelotti won everything by using as many fantasista as possible – Rui Costa, Andrea Pirlo, Clarence Seedorf and Kaká to name a few – and those midfield magicians helped Milan conquer Europe in 2002/03 and 2006/07.

As the game continues to evolve, his son’s modern sensibility has proved indispensable. “A coach needs to adapt to football, which is ever-changing, to remain at such a high level for so long,” Davide explains. “Since the 1990s, he’s been able to keep up with the times and make a mental effort to stay up to date and listen. Another of his traits is that he can listen, which has always allowed him to stay in touch. I mostly challenge him. Generally speaking, all his staff do. I try to do that because I know it’s good for him.”

While Davide helps his father stay young, there is a neat symmetry at the other end of the spectrum. “Age doesn’t define people,” says Ancelotti Sr, talking not about himself but the ability of young talents to make an impact. “You can be very mature at 20 and a bit childish at 40.” And who better to prove his theory than Madrid’s latest gem, Jude Bellingham? The former Dortmund midfielder turned 20 in June, but already he is performing with the self-assurance of a veteran, much to his coach’s delight. “He has absolutely exceeded our expectations, especially in terms of scoring. He’s scored many goals. He’s settling in very well. He’s very young but very mature: he has a strong personality and character, and it’s helped him integrate into the club so confidently. He doesn’t seem like a 20-year-old. I believe his experience in Germany helped him a lot and made him even more mature.”

Bellingham’s thrilling start has Madrid fans dreaming of a long era of success, potentially stretching well beyond Ancelotti’s own reign. But while his love of the game shows no sign of waning for now, the Italian is not afraid to think about life after football. “Just as it never worried me when I was playing,” he says. “I knew I would find something to do. Travelling, for sure. There are plenty of places I’ve never seen: Australia, Argentina. With more time on my hands, I can spend it with my family, my grandchildren – I have five. I’ll have plenty to do. I’m not worried about what comes after.”

As Carlo Ancelotti closes in on becoming the first man to coach 200 games in the Champions League, we take a look at some of the records he holds in a staggering career so far

When Carlo Ancelotti lifted the Champions League trophy in 2021/22, he moved into a class of his own as the first coach to win the competition four times. It was one more landmark achievement for a man who continues to break new ground, his most recent European title also coming a record 19 years after his first with AC Milan in 2002/03.

Now in his fourth decade coaching in the Champions League, the Real Madrid boss likewise belongs to a select club of six managers to have led two different teams to the European summit – and one of only two in that group, along with Pep Guardiola, to have claimed the honour as a player as well. Unlike Guardiola, however, he has also won domestic titles in each of Europe’s top five leagues, a historic first which he completed in Spain two seasons ago.

“Being a football coach is not a duty; it’s a desire,” says the veteran Italian, explaining his ability to stay at the top since beginning his management career as an assistant coach with Italy in 1992. “What carries you forward in this sport is your passion, but you need patience as well.”

Desire, passion and patience. Ancelotti still displays plenty of each as he approaches another Champions League milestone. Masterminding a perfect six wins in this season’s group stage, then Madrid’s round of 16 triumph against Leipzig took him to 114 victories from 199 matches in the competition. Not only are both those figures records, they leave him tantalisingly close to breaking the 200-game barrier. Onwards and upwards…

I first interviewed Ancelotti at Milanello, AC Milan’s training base, back in 2002. Already, he had come a long way since his youth in Reggiolo, the picturesque rural commune in Reggio Emilia known for its medieval fortress, annual pumpkin festival and – this will come as no surprise – the humble outlook of the locals. Milan were in the middle of their triumphant 2002/03 campaign, when Ancelotti led them to Champions League glory by beating his former side Juventus on penalties in the final. Our interview was scheduled for the morning, but we were later told we had to wait until the afternoon. While I was planning to get sandwiches for lunch with the rest of the crew, Ugo – a veteran of the Rossoneri press office and one of the nicest people I have met in football – came over and said the boss had invited us to eat with him and the team in their dining room.

It was my first season as reporter, and I was in my late 20s. I thanked them calmly and politely, but on the inside I was anything but calm, my head pounding with a single thought: “What???” I could hardly believe my eyes as I sat in the same room with Ancelotti and the entire team. The conversation was easy, the food was delicious, and occasionally the likes of Clarence Seedorf and Gennaro Gattuso would perch down and talk with Ancelotti about anything and everything. He did all he could to make us feel comfortable. He himself was completely at home at Milanello, of course. As a player, he had spent five seasons there, winning the European Cup twice among numerous trophies in the legendary team coached by Arrigo Sacchi. Now here he was in a different role, chatting and joking with the staff, from the chef to the cleaners, and all the while he was building one of the most spectacular sides in Europe.

When I meet with Ancelotti again at Madrid’s beautiful training ground, I cannot help noticing that not much has changed since we first crossed paths 21 years ago. True, I am also here to speak with Davide, one of his right-hand men as opposed to the 13-year-old boy he would have been then. And Carlo is carrying a few more grey hairs these days, but he is probably even fitter than he was at Milan – and his relaxed and humble approach remains the same. So too that famous eyebrow which arches suddenly when he tackles my questions.

Now a record four-time Champions League winner as a coach, Ancelotti would have every right to proclaim his opinions like a preacher from a pulpit, but instead he is as modest as he was before the first of those victories. “One key element is probably that I coached two clubs that care a great deal about this competition,” he says when asked the secret to his European triumphs. “It’s no coincidence that both Milan and Real Madrid are among the most successful clubs in the history of this competition, and this competition represents the most important trophy for both clubs. I don’t know what kind of mark I have left.”

Even so, I push him harder to open up about his huge personal contribution, reminding him of his key role in Madrid’s landmark tenth European title in 2013/14. “La Décima has your name all over it,” I tell him. “Yes, I mean, with Real Madrid I won two tournaments that will go down in history: La Décima and the 14th title, which were both inspired and inspirational at the same time.”

Well, it was worth a try. And, besides, we all know how crucial his influence was. Indeed, less than two years on from the second of those continental crowns, in 2021/22, his hunger is undiminished. “What helps me stay on top of my game is the passion I have for this sport,” he says. “I had it when I started playing as a kid, and I still have it today. It’s a very strong passion which luckily did not turn into an obsession. When you become a coach, you risk turning your passion into obsession. Football remains a great passion for me. When I have some free time and there’s a football game on, I’ll watch it, but I really enjoy films too. I love being with my family, my children, my grandchildren and my wife.”

That emphasis on personal relationships has undoubtedly helped him build strong bonds in every team he has overseen. You’d be hard pressed to hear any negative comments from his former players, a long list which includes some of the best footballers in the history of the game.

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“Respecting the footballer is fine, but it’s much more important to respect the person behind the footballer”
Carlo Ancelotti celebrates the first of his two Champions League triumphs with Real Madrid, against rivals Atlético in Lisbon in 2014

“Respecting the footballer is fine, but I think it’s much more important to respect the person behind the footballer,” Ancelotti explains. “That’s my general approach. I’m not just a football coach, I’m a person who works as a coach. My own character was moulded by growing up with the people I consider my mentors, starting with my parents, and also my teachers and coaches. I always carry myself with the footballers I work with by focusing on them as people first and foremost.”

If anyone could query that assessment, it would be Davide, his son and assistant at the Santiago Bernabéu. Quite the opposite, in fact. “Both as a father and as a coach, he’s able to be authentic, to be himself, which means someone who cares a lot about his family members and his children,” he tells us. “The same goes for the players: he’s a very affectionate person both at work and in his personal life. He’s a very quiet person and there are never many conflicts with him. As a coach and as a father, he’s able to maintain a peaceful environment, the same as the one I grew up in when I was little. Objectively, there are very few differences between the father and the coach. I would say that the differences are almost non-existent. That’s why many players say they had a father-son relationship with him.”

A former footballer who played in the Milan youth system, Davide hung up his boots in 2009 when he was only 20 to pursue a career in management. He completed a Sports Science degree in 2011 and one year later started to work with his father as fitness coach at Paris Saint-Germain. He followed Carlo to Madrid, where he met his partner Ana, and in 2016 he received a UEFA A licence. Now 34, his eyes light up when he talks about his father, and their hug after Madrid’s incredible comeback against Manchester City in the 2021/22 Champions League semi-finals – on the anniversary of his late mother’s birthday – will always remain one of the most touching moments of that memorable campaign.

“I don’t remember when he was a footballer because he retired when I was four, but I recall we had this videotape at home with all his goals,” says Davide. “It wasn’t long as he didn’t score many, so I remembered them all. After watching it, I knew all those goals by heart. Naturally, I have more memories from when he became a coach. I remember being a very shy kid and, after the games, he would ask me to come back with the team on the coach, but I was so embarrassed that I couldn’t. I used to cry because I actually wanted to go, but I would say no in the moment because I was afraid of being there with Zinédine Zidane and Alessandro Del Piero, who were my idols. He would say, ‘Are you sure? You’ll regret it!’ That’s a memory I have from when he coached Juventus and I was a kid of eight.”

Ancelotti’s warm personality does not tell the full story, however. His flexibility and eagerness to study the latest football tactics have always been valuable attributes. He was a 4-4-2 fanatic early in his career, so much so that he famously refused to have a certain Roberto Baggio in his team because the Italy great did not fit into his system. A few years later, Ancelotti won everything by using as many fantasista as possible – Rui Costa, Andrea Pirlo, Clarence Seedorf and Kaká to name a few – and those midfield magicians helped Milan conquer Europe in 2002/03 and 2006/07.

As the game continues to evolve, his son’s modern sensibility has proved indispensable. “A coach needs to adapt to football, which is ever-changing, to remain at such a high level for so long,” Davide explains. “Since the 1990s, he’s been able to keep up with the times and make a mental effort to stay up to date and listen. Another of his traits is that he can listen, which has always allowed him to stay in touch. I mostly challenge him. Generally speaking, all his staff do. I try to do that because I know it’s good for him.”

While Davide helps his father stay young, there is a neat symmetry at the other end of the spectrum. “Age doesn’t define people,” says Ancelotti Sr, talking not about himself but the ability of young talents to make an impact. “You can be very mature at 20 and a bit childish at 40.” And who better to prove his theory than Madrid’s latest gem, Jude Bellingham? The former Dortmund midfielder turned 20 in June, but already he is performing with the self-assurance of a veteran, much to his coach’s delight. “He has absolutely exceeded our expectations, especially in terms of scoring. He’s scored many goals. He’s settling in very well. He’s very young but very mature: he has a strong personality and character, and it’s helped him integrate into the club so confidently. He doesn’t seem like a 20-year-old. I believe his experience in Germany helped him a lot and made him even more mature.”

Bellingham’s thrilling start has Madrid fans dreaming of a long era of success, potentially stretching well beyond Ancelotti’s own reign. But while his love of the game shows no sign of waning for now, the Italian is not afraid to think about life after football. “Just as it never worried me when I was playing,” he says. “I knew I would find something to do. Travelling, for sure. There are plenty of places I’ve never seen: Australia, Argentina. With more time on my hands, I can spend it with my family, my grandchildren – I have five. I’ll have plenty to do. I’m not worried about what comes after.”

As Carlo Ancelotti closes in on becoming the first man to coach 200 games in the Champions League, we take a look at some of the records he holds in a staggering career so far

When Carlo Ancelotti lifted the Champions League trophy in 2021/22, he moved into a class of his own as the first coach to win the competition four times. It was one more landmark achievement for a man who continues to break new ground, his most recent European title also coming a record 19 years after his first with AC Milan in 2002/03.

Now in his fourth decade coaching in the Champions League, the Real Madrid boss likewise belongs to a select club of six managers to have led two different teams to the European summit – and one of only two in that group, along with Pep Guardiola, to have claimed the honour as a player as well. Unlike Guardiola, however, he has also won domestic titles in each of Europe’s top five leagues, a historic first which he completed in Spain two seasons ago.

“Being a football coach is not a duty; it’s a desire,” says the veteran Italian, explaining his ability to stay at the top since beginning his management career as an assistant coach with Italy in 1992. “What carries you forward in this sport is your passion, but you need patience as well.”

Desire, passion and patience. Ancelotti still displays plenty of each as he approaches another Champions League milestone. Masterminding a perfect six wins in this season’s group stage, then Madrid’s round of 16 triumph against Leipzig took him to 114 victories from 199 matches in the competition. Not only are both those figures records, they leave him tantalisingly close to breaking the 200-game barrier. Onwards and upwards…

I first interviewed Ancelotti at Milanello, AC Milan’s training base, back in 2002. Already, he had come a long way since his youth in Reggiolo, the picturesque rural commune in Reggio Emilia known for its medieval fortress, annual pumpkin festival and – this will come as no surprise – the humble outlook of the locals. Milan were in the middle of their triumphant 2002/03 campaign, when Ancelotti led them to Champions League glory by beating his former side Juventus on penalties in the final. Our interview was scheduled for the morning, but we were later told we had to wait until the afternoon. While I was planning to get sandwiches for lunch with the rest of the crew, Ugo – a veteran of the Rossoneri press office and one of the nicest people I have met in football – came over and said the boss had invited us to eat with him and the team in their dining room.

It was my first season as reporter, and I was in my late 20s. I thanked them calmly and politely, but on the inside I was anything but calm, my head pounding with a single thought: “What???” I could hardly believe my eyes as I sat in the same room with Ancelotti and the entire team. The conversation was easy, the food was delicious, and occasionally the likes of Clarence Seedorf and Gennaro Gattuso would perch down and talk with Ancelotti about anything and everything. He did all he could to make us feel comfortable. He himself was completely at home at Milanello, of course. As a player, he had spent five seasons there, winning the European Cup twice among numerous trophies in the legendary team coached by Arrigo Sacchi. Now here he was in a different role, chatting and joking with the staff, from the chef to the cleaners, and all the while he was building one of the most spectacular sides in Europe.

When I meet with Ancelotti again at Madrid’s beautiful training ground, I cannot help noticing that not much has changed since we first crossed paths 21 years ago. True, I am also here to speak with Davide, one of his right-hand men as opposed to the 13-year-old boy he would have been then. And Carlo is carrying a few more grey hairs these days, but he is probably even fitter than he was at Milan – and his relaxed and humble approach remains the same. So too that famous eyebrow which arches suddenly when he tackles my questions.

Now a record four-time Champions League winner as a coach, Ancelotti would have every right to proclaim his opinions like a preacher from a pulpit, but instead he is as modest as he was before the first of those victories. “One key element is probably that I coached two clubs that care a great deal about this competition,” he says when asked the secret to his European triumphs. “It’s no coincidence that both Milan and Real Madrid are among the most successful clubs in the history of this competition, and this competition represents the most important trophy for both clubs. I don’t know what kind of mark I have left.”

Even so, I push him harder to open up about his huge personal contribution, reminding him of his key role in Madrid’s landmark tenth European title in 2013/14. “La Décima has your name all over it,” I tell him. “Yes, I mean, with Real Madrid I won two tournaments that will go down in history: La Décima and the 14th title, which were both inspired and inspirational at the same time.”

Well, it was worth a try. And, besides, we all know how crucial his influence was. Indeed, less than two years on from the second of those continental crowns, in 2021/22, his hunger is undiminished. “What helps me stay on top of my game is the passion I have for this sport,” he says. “I had it when I started playing as a kid, and I still have it today. It’s a very strong passion which luckily did not turn into an obsession. When you become a coach, you risk turning your passion into obsession. Football remains a great passion for me. When I have some free time and there’s a football game on, I’ll watch it, but I really enjoy films too. I love being with my family, my children, my grandchildren and my wife.”

That emphasis on personal relationships has undoubtedly helped him build strong bonds in every team he has overseen. You’d be hard pressed to hear any negative comments from his former players, a long list which includes some of the best footballers in the history of the game.

“Respecting the footballer is fine, but it’s much more important to respect the person behind the footballer”
Carlo Ancelotti celebrates the first of his two Champions League triumphs with Real Madrid, against rivals Atlético in Lisbon in 2014

“Respecting the footballer is fine, but I think it’s much more important to respect the person behind the footballer,” Ancelotti explains. “That’s my general approach. I’m not just a football coach, I’m a person who works as a coach. My own character was moulded by growing up with the people I consider my mentors, starting with my parents, and also my teachers and coaches. I always carry myself with the footballers I work with by focusing on them as people first and foremost.”

If anyone could query that assessment, it would be Davide, his son and assistant at the Santiago Bernabéu. Quite the opposite, in fact. “Both as a father and as a coach, he’s able to be authentic, to be himself, which means someone who cares a lot about his family members and his children,” he tells us. “The same goes for the players: he’s a very affectionate person both at work and in his personal life. He’s a very quiet person and there are never many conflicts with him. As a coach and as a father, he’s able to maintain a peaceful environment, the same as the one I grew up in when I was little. Objectively, there are very few differences between the father and the coach. I would say that the differences are almost non-existent. That’s why many players say they had a father-son relationship with him.”

A former footballer who played in the Milan youth system, Davide hung up his boots in 2009 when he was only 20 to pursue a career in management. He completed a Sports Science degree in 2011 and one year later started to work with his father as fitness coach at Paris Saint-Germain. He followed Carlo to Madrid, where he met his partner Ana, and in 2016 he received a UEFA A licence. Now 34, his eyes light up when he talks about his father, and their hug after Madrid’s incredible comeback against Manchester City in the 2021/22 Champions League semi-finals – on the anniversary of his late mother’s birthday – will always remain one of the most touching moments of that memorable campaign.

“I don’t remember when he was a footballer because he retired when I was four, but I recall we had this videotape at home with all his goals,” says Davide. “It wasn’t long as he didn’t score many, so I remembered them all. After watching it, I knew all those goals by heart. Naturally, I have more memories from when he became a coach. I remember being a very shy kid and, after the games, he would ask me to come back with the team on the coach, but I was so embarrassed that I couldn’t. I used to cry because I actually wanted to go, but I would say no in the moment because I was afraid of being there with Zinédine Zidane and Alessandro Del Piero, who were my idols. He would say, ‘Are you sure? You’ll regret it!’ That’s a memory I have from when he coached Juventus and I was a kid of eight.”

Ancelotti’s warm personality does not tell the full story, however. His flexibility and eagerness to study the latest football tactics have always been valuable attributes. He was a 4-4-2 fanatic early in his career, so much so that he famously refused to have a certain Roberto Baggio in his team because the Italy great did not fit into his system. A few years later, Ancelotti won everything by using as many fantasista as possible – Rui Costa, Andrea Pirlo, Clarence Seedorf and Kaká to name a few – and those midfield magicians helped Milan conquer Europe in 2002/03 and 2006/07.

As the game continues to evolve, his son’s modern sensibility has proved indispensable. “A coach needs to adapt to football, which is ever-changing, to remain at such a high level for so long,” Davide explains. “Since the 1990s, he’s been able to keep up with the times and make a mental effort to stay up to date and listen. Another of his traits is that he can listen, which has always allowed him to stay in touch. I mostly challenge him. Generally speaking, all his staff do. I try to do that because I know it’s good for him.”

While Davide helps his father stay young, there is a neat symmetry at the other end of the spectrum. “Age doesn’t define people,” says Ancelotti Sr, talking not about himself but the ability of young talents to make an impact. “You can be very mature at 20 and a bit childish at 40.” And who better to prove his theory than Madrid’s latest gem, Jude Bellingham? The former Dortmund midfielder turned 20 in June, but already he is performing with the self-assurance of a veteran, much to his coach’s delight. “He has absolutely exceeded our expectations, especially in terms of scoring. He’s scored many goals. He’s settling in very well. He’s very young but very mature: he has a strong personality and character, and it’s helped him integrate into the club so confidently. He doesn’t seem like a 20-year-old. I believe his experience in Germany helped him a lot and made him even more mature.”

Bellingham’s thrilling start has Madrid fans dreaming of a long era of success, potentially stretching well beyond Ancelotti’s own reign. But while his love of the game shows no sign of waning for now, the Italian is not afraid to think about life after football. “Just as it never worried me when I was playing,” he says. “I knew I would find something to do. Travelling, for sure. There are plenty of places I’ve never seen: Australia, Argentina. With more time on my hands, I can spend it with my family, my grandchildren – I have five. I’ll have plenty to do. I’m not worried about what comes after.”

As Carlo Ancelotti closes in on becoming the first man to coach 200 games in the Champions League, we take a look at some of the records he holds in a staggering career so far

When Carlo Ancelotti lifted the Champions League trophy in 2021/22, he moved into a class of his own as the first coach to win the competition four times. It was one more landmark achievement for a man who continues to break new ground, his most recent European title also coming a record 19 years after his first with AC Milan in 2002/03.

Now in his fourth decade coaching in the Champions League, the Real Madrid boss likewise belongs to a select club of six managers to have led two different teams to the European summit – and one of only two in that group, along with Pep Guardiola, to have claimed the honour as a player as well. Unlike Guardiola, however, he has also won domestic titles in each of Europe’s top five leagues, a historic first which he completed in Spain two seasons ago.

“Being a football coach is not a duty; it’s a desire,” says the veteran Italian, explaining his ability to stay at the top since beginning his management career as an assistant coach with Italy in 1992. “What carries you forward in this sport is your passion, but you need patience as well.”

Desire, passion and patience. Ancelotti still displays plenty of each as he approaches another Champions League milestone. Masterminding a perfect six wins in this season’s group stage, then Madrid’s round of 16 triumph against Leipzig took him to 114 victories from 199 matches in the competition. Not only are both those figures records, they leave him tantalisingly close to breaking the 200-game barrier. Onwards and upwards…

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