Real Madrid coach Carlo Ancelotti was in typically relaxed form when he spoke to the media before Tuesday’s La Liga game at home to Deportivo Alaves this week.

“I’ve been lucky enough to coach 300 games at the best club in the world,” Ancelotti said. “To be on this bench is something special. To sit there 300 times… I’m not saying it’s a miracle, but almost.”

To reach such a milestone at any big European club is a superb achievement. It is especially impressive at Real Madrid, given president Florentino Perez’s history of hiring and firing coaches. Only one manager has taken charge of more games at Madrid: Miguel Munoz, with 605 between 1959 and 1974.

It helps that during both of Ancelotti’s spells as Madrid manager (he was in charge from 2013-2015 and returned in 2021) the team won the Champions League, first in 2014 and then in 2022 and 2024. But winning trophies alone is often not enough to ensure job security at the Bernabeu.

Just 12 months after delivering Madrid’s long-awaited tenth European Cup in 2014, Ancelotti was fired by Perez as serious issues arose in their relationship. His second spell has also featured several rocky moments — while also delivering two more Champions League titles.

To survive, and thrive, in arguably the most demanding environment in football is, as Ancelotti himself recognised this week, almost miraculous.

So how has he done it?

Over almost three decades working as a manager (he started at Italian club Reggiana in 1995), Ancelotti has acquired plenty of experience working for big characters used to issuing orders and seeing them quickly followed.

At AC Milan (2001-2009), Silvio Berlusconi was the owner — as well as the domineering prime minister of Italy for part of Ancelotti’s spell. His ultimate boss at Chelsea (2009-2011) was Roman Abramovich, a secretive Russian oligarch. At Paris Saint-Germain (2011-2013), the president was Nasser Al Khelaifi, a close associate of the ruling powers in Qatar.

Between his spells at Madrid his superiors were Bayern Munich’s self-confident president Uli Hoeness (Ancelotti was there for 2016-17), Napoli’s larger-than-life president Aurelio de Laurentiis (during 2018-19) and Everton’s majority owner Farhad Moshiri (2019-2021).

Ancelotti’s 2016 book — Quiet Leadership: winning hearts, minds and matches — includes a whole section on “managing up”, discussing his experiences dealing with colourful and powerful bosses.

Co-written with former Chelsea director Mike Forde and management consultant Chris Brady, it was published between the Italian being fired by Madrid in June 2015 and him joining Bayern the following summer.

At Milan, Ancelotti wrote, it soon became clear certain realities had to be accepted: “With Berlusconi I learned very quickly that, since he owned Milan, my job was to please Berlusconi.”

Ancelotti and Silvio Berlusconi pictured in January 2006 (Giuseppe Cacace/AFP via Getty Images)

On joining Chelsea, Abramovich instructed him to play a possession-based style of football. To do so, Ancelotti asked for playmaker Andrea Pirlo but when that was not possible, he used Michael Essien in that role. The book does not complain, but readers will know these are two very different types of players.

Ancelotti could handle not getting everything he wanted in the transfer market but it was more problematic that every time Chelsea lost a game, Abramovich arrived to personally demand answers.

“(That) taught me how to deal with this different kind of president,” Ancelotti wrote in his book. “I chose not to meet aggression with aggression, it is not my way. I like to think through difficult times, address the problems coolly and with reason.”

Ancelotti decided to use the owner’s interference in his job to motivate the team — and they won a Premier League and FA Cup double in his first season in charge. He wrote that the players knew Abramovich was “on my case” and they “responded brilliantly”.

It was difficult for that approach to succeed in the long term, and Abramovich fired Ancelotti after the following season ended trophyless. Next, he joined PSG, where the general director was Leonardo, “a friend of mine from Milan”.

Within 12 months it was clear things were not going to work out. After PSG lost to Ligue 1 rival Nice in December 2012, Leonardo told him he would be sacked if they did not beat Porto in their next game. Ancelotti realised Al Khelaifi had decided that the ‘project’ was not working, so he informed his bosses he would leave at the end of the season.

Next stop was the Bernabeu, where Ancelotti quickly realised he should just focus on coaching the first team and not worry about things outside his control. In his book, he wrote about realising “you are only ever a piece of the project” at Real Madrid. He said accepting that liberated him to focus on getting the best out of his players.

Following three seasons of predecessor Jose Mourinho’s pragmatic approach, Perez wanted a more attractive style of football at Madrid. Ancelotti set to work, allowing senior figures Sergio Ramos, Xabi Alonso, Cristiano Ronaldo and Luka Modric greater responsibility. He also devised new roles for Gareth Bale and Angel Di Maria within a 4-3-3 tactical shape. It delivered ‘La Decima’ in his first season.

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The strength of the relationships Ancelotti built is shown by Ronaldo guest-writing a chapter in Quiet Leadership.

“One of the reasons the atmosphere was so good was because Carlo protected the dressing room from the president and anything else that might upset the balance of the family,” Ronaldo wrote. “I’ve seen that he does not bow to pressure from anyone: he makes his own decisions.”

Ancelotti and Ronaldo celebrate reaching the 2014 Champions League final (Stuart Franklin – UEFA/UEFA via Getty Images)

Yet not all was perfect. Quiet Leadership also tells of Perez informing Ancelotti that Bale’s agent said his client wanted to play more centrally on the pitch. The Italian spoke directly with the player, explaining the team’s setup, and his vital role in it. He also used a press conference to tell the agent to “shut up”. Ancelotti wrote that this changed his relationship with Perez.

When Madrid lost a few games in early 2015, the club hierarchy grew concerned at a report claiming that Madrid’s training sessions were not intense enough. Ancelotti thought the squad needed more rest, especially with important players Ramos and Modric injured. The issue was never resolved, and when the season ended without a major trophy, the axe came.

Ancelotti wrote that his time at Madrid was “shorter than he’d hoped, but also longer than many who manage there”.

He added: “Leading may sometimes involve compromise, especially at the biggest clubs, but not when it comes to your expertise and you have the conviction of your decisions.”

Returning to Madrid in summer 2021, Ancelotti was well aware of the issues that caused friction the first time around. He accepted without complaint the club adding fitness coach Antonio Pintus to his staff, and repeated often that energy and physicality were vital for success in today’s game.

But he also insisted on bringing his own son Davide, then 34, as his assistant coach. This raised eyebrows at the Bernabeu, where the number two has often been a former club legend with the president’s ear. Ancelotti talks in his book a lot about how his closest staff are like a family. Now that was literally the case.

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Ancelotti was also well aware that the president would continue to have the final say on transfer policy. That meant adapting tactics to the current squad. The team sat deeper, meaning less running for veteran midfielders Toni Kroos and Modric, and more space for Vinicius Junior to exploit. Balance came from midfielder Federico Valverde on the right wing. It paid off when Valverde assisted Vinicius Jr’s winning goal in the 2021-22 Champions League final against Liverpool.

Ancelotti is mobbed after Madrid’s victory in the 2022 Champions League final (Jose Breton/Pics Action/NurPhoto via Getty Images)

When Karim Benzema left for Saudi Arabia in summer 2023, Ancelotti wanted England captain Harry Kane as a direct replacement. That option was not seriously pursued by Perez, so instead he created a new attacking role for Jude Bellingham, who scored 23 goals as Madrid won the La Liga and Champions League double last season.

Such success was far from inevitable. In May 2023, Madrid were thrashed 4-0 by Pep Guardiola’s City in a decisive Champions League semi-final second leg, just as Xavi’s Barcelona were easily winning the La Liga title. It was a rocky spell not unlike that which ended Ancelotti’s first term at the Bernabeu.

Ancelotti had an easy escape route — Brazil wanted him as their next national coach. His first option was always to remain in the Spanish capital, but speculation continued well into the 2023-24 campaign, with Ancelotti’s contract due to expire in June 2025.

It was an awkward situation, as Perez is not used to any coach having such strong bargaining power. The Bernabeu hierarchy considered other options, including Bayer Leverkusen coach Alonso. Meanwhile, Ancelotti’s team went on a 17-game unbeaten run, winning 14 and drawing three, including a 2-1 Clasico victory at Barcelona, putting them in control of the La Liga title race. In late December, he was offered an extension to 2026 and accepted.

“I can’t control the direction of the president, I can only hope to influence him, and the best way to do that is by winning,” Ancelotti wrote in his 2016 book.

There was another awkward moment just last month. The Ancelottis wanted Madrid to hire 38-year-old Stockport County coach Andy Mangan, who is close to Davide. Not everyone at the Bernabeu liked the idea, and in the end the Spanish authorities refused Mangan a work permit.

That came amid a feeling around the Bernabeu that Madrid have not started the new season well, with departed playmaker Kroos badly missed. Stuttgart having more possession (54 per cent to Madrid’s 46 per cent) in last week’s Champions League group game at the Bernabeu fed a debate about the team’s style of play (even though Madrid won 3-1).

Afterwards, Ancelotti faced tough questioning from reporters well aware that Perez prefers to see his team dominating possession and playing stylish attacking football.

“Maybe we could play better, but Real Madrid fans are used to seeing ‘rock and roll’ football, not lots of touches,” he responded coolly. “We try, with our characteristics, to make the fans happy. The fans like winning more than playing well. The ideal is to win and play well.”

Ancelotti with his Real Madrid players in pre-season this August (Victor Carretero/Real Madrid via Getty Images)

It was typical Ancelotti. He made the point that his squad, especially in midfield and attack, is made up of players suited to football that is “entertaining, direct, intense, with pace”. The underlying message was that he was making the best of the players available, while everyone knew he was not primarily responsible for assembling the squad. It was all delivered calmly, showing he was in control of the situation and nobody should worry.

Not all top managers react to criticism, or interference from above, in such a way. With some, their ego gets in the way. But at this stage of his career, and his life, the 65-year-old Ancelotti has sufficient self confidence to not react to treatment others might take personally. His experience of dealing with many different owners and presidents has taught him to be philosophical.

“I’ve learned that getting sacked — and getting recruited for that matter — is rarely just about you,” Ancelotti wrote in Quiet Leadership. “It is always about the person hiring or firing you. Do your job to the best of your ability and let others judge you because they will anyway.”

In another section of the book, he puts it differently.

“As Vito Corleone would have said in one of my favourite movies, The Godfather, ‘It’s not personal. It’s just business.’”

(Top photo: Angel Martinez – UEFA/UEFA via Getty Images)

With the Pittsburgh Pirates out of playoff contention, first baseman Rowdy Tellez was playing for an opportunity to receive a $200,000 bonus based on plate appearances. He entered Tuesday with 421 plate appearances, four away from earning that additional bonus.

For Tellez, the chance was dashed. With five games left in the regular season, the Pirates designated  Tellez for assignment before their Tuesday game against the Milwaukee Brewers. With MLB in the final week of its regular season, Tellez will likely end his 2024 campaign at 421 plate appearances, four shy of the 425 needed to earn an extra $200,000.

Pirates general manager Ben Cherington told reporters that the potential for a $200,000 bonus didn’t impact his decision to remove Tellez from the roster.

“We feel like we gave Rowdy lots of opportunity here this year,” Cherington said Tuesday.

The Pirates signed Tellez to a one-year, $3.2 million deal in the offseason. Through 383 at bats in 2024, Tellez slashed .243/.299/.392 with 13 home runs and 56 RBIs. While his overall numbers are an improvement from last year (.215/.291/.376 with 13 home runs and 47 RBIs in 2023), it’s a decline from 2022, where he set a career high in homers (35), RBIs (89) and hits (116).

Tellez struggled to start the 2024 season, tallying just one home run through May. But he improved as the season progressed, the exclamation point happening on July 5 when he hit a homer and a grand slam en route to a 14-2 drubbing over the New York Mets that caused Pittsburgh to run out of fireworks. 

The Pirates were trade deadline buyers and entered August chasing a playoff spot. But a 10-game losing streak at the beginning of the month effectively ended the Pirates’ playoff hopes. The Pirates were eliminated from playoff contention on Sept. 16. Eight days later, the team DFA’d Tellez.

MLB players in their contracts are eligible to receive bonuses through the incentive clause according to the CBA. Per MLB’s Basic Agreement, incentives based on statistical achievement are prohibited. This means predetermined, non-statistical benchmarks allow players to earn extra money. For hitters, the most common incentive is plate appearances. Staying on the active roster for a certain number of days can also earn a bonus, depending on the contract.

The Pirates lost 7-2 to the Brewers on Tuesday, falling to 73-84 in 2024. In addition to Tellez, the Pirates also designated outfielder Michael A. Taylor for assignment.

(Photo: Jason Mowry / Getty Images)

Football shirts were once an item of clothing for a) players to wear at work, and b) fans to sport on the terraces in solidarity with the lads out on the pitch.

Now, what must seem abruptly to the uninitiated, they have become the uniform for British music festivals and a source of inspiration for major fashion houses.

Several moments signalled the shift to football shirts becoming mainstream during the 2010s.

For example, Drake, the Canadian music artist, wore the 2015-16 season’s pink away shirt of leading Italian club Juventus, leading to an internet scramble from his fanbase. And two years later, the landscape changed completely again when Nigeria unveiled their kit for the 2018 World Cup finals.

“After 2016, we’d seen quite a few years of blank kits,” says Phil Delves, a kit collector, designer and influencer. “Many people rightly refer to the Nigeria kit (in 2018) and the interest around that, and I think while the design itself isn’t the craziest design we’ve seen, everything was massively amplified because of the moment it arrived and the fact it was coupled with a major tournament.”

Juventus in Pink

2015 – The latest instalment of the Juve pink kit was seen in 2015. It wasn’t just made famous by the big names, such as Pogba, on the pitch but reached a larger audience thanks to rapper Drake.

Hopefully there will be another great pink kit soon! pic.twitter.com/BGoucrstPM

— Classic Football Shirts (@classicshirts) August 2, 2018

Before Nigeria took to the pitch at that tournament in Russia, the shirt they wore as they did so had taken on a life of its own. Designed by American artist Matthew Wolff as a tribute to that African nation’s performance in reaching the knockout phase of the 1994 World Cup, in what was their debut on the global stage, the kit featured a green and white torso with triangle-patterned black and white sleeves.

The bold and vibrant design in 2018 represented the nation’s history and an emerging ‘Naija’ culture centred on a hopeful view of the country’s future, embodied by a new generation of exciting players and a growing arts sector.

Following the kit announcement, internationally famous music artists, including Wizkid, the Nigerian singer from whom Bukayo Saka has borrowed the ‘Starboy’ nickname, and Skepta, a rapper born and raised in London to Nigerian parents, wore the shirt.

At the same time, England were enjoying their most successful international tournament since making the semi-finals of the 1996 European Championship, and staunch and casual fans alike went shopping for retro kits to wear while watching the games.

Shortly after that 2018 World Cup, serial French champions Paris Saint-Germain announced a collaboration with Nike’s Jordan Brand worth around €200million (£168m; $223m at current exchange rates). The striking black-and-white kits produced under the deal drew eyes from around the world as global superstars in football, including Neymar and recent World Cup winner Kylian Mbappe, played for PSG in the Champions League wearing a logo associated with U.S. basketball legend Michael Jordan.

This was not the first time PSG had taken inspiration from other fashion sectors — their 2006-07 Louis Vuitton-inspired away kit was among the first of its kind — but it marked a period when the once-niche collaboration between fashion and football went mainstream.

PSG’s Louis Vuitton-inspired away kit from 2006-07 (Pascal Pavani/AFP via Getty Images)

“For us as a business, the summer of 2018 is a real turning point,” says Doug Bierton, CEO and co-founder of Classic Football Shirts. “We opened our first retail store in London, and we got to see first-hand the passion and hype.”

Classic Football Shirts started life in 2006 when Bierton and co-founder Matt Dale went searching for a Germany kit from the 1990 World Cup for a fancy dress party. After purchasing the shirt from eBay, and an England one with Paul Gascoigne’s name printed on the back, the duo noted the dearth of authentic retro jerseys available online.

Bierton and Dale set up a business to buy and sell football shirts, reinvesting their profits into new stock. Less than two decades later, Classic Football Shirts has more than 1.3 million Instagram followers, stores in major cities in the UK and the United States and expects revenues north of $50million in 2024.

Following a $38.5million (£29m) cash injection from investment firm The Chernin Group in May, the company announced several other strategic investors this month. The new investors include actor and Wrexham co-owner Rob McElhenney, recently retired USWNT legend Alex Morgan and global sports and entertainment agency Wasserman.

Bierton is as equipped as anybody to chart how the business has developed from a relatively niche collector industry into one of the most prominent subcultures within football and fashion.

A model wearing a football shirt at the 2018 Paris Fashion Week (Christian Vierig/Getty Images)

“It was much more underground,” says Bierton. “It was only after the 1994 World Cup and the advent of the Premier League that football shirts started being produced with any volume, so when we set up the company in 2006, there was a limited range to look back to. When we began, shirts from the 1980s were more fashionable — like, indie style, the skinny Adidas trefoil type.

“People weren’t buying 1990s shirts from a fashion point of view because the baggy stuff wasn’t really on-trend. It was more ‘I want to get a David Beckham shirt because I’m into shirt collecting or just football in general’. But as the years go by, kids get older. People are harking back to different eras.”

Still, diehard football fans are only a portion of the industry.

Over the years, high-end fashion brands including Giorgio Armani, Dior, Stella McCartney, Yohji Yamamoto and Balenciaga have partnered with football teams to design special kits. Celebrities with no apparent ties to the sport, such as pop stars Rihanna and Sabrina Carpenter — the latter wore an England shirt over a Versace dress at the ‘Capital Summertime Ball’ festival in the UK during the recent Euros — have jumped on the hype train.

With the rise of ‘Blokecore’, an internet trend popularised on TikTok where people of all ages and genders wear retro football shirts with casual outfits, there are no limits on who wears these kits or where.

“We did a string of pop-ups in the autumn in the U.S. last year, and the turnout was insane,” says Bierton. “We had lines down the block in Los Angeles, New York and Miami.

“It was unbelievable to see the range of stuff people were wearing. It was a combination of hardcore fans who loved the game and wanted a shirt to show their knowledge and passion and those who think football shirts are pretty cool to wear. We had someone ask a customer why they were wearing an old Sheffield Wednesday shirt, and they responded, ‘I don’t even know what Sheffield Wednesday is!’.”

Some old football shirts are worth more than others (Adrian Dennis/AFP via Getty Images)

As the industry has grown, the chances of strolling into a charity shop and finding a rare shirt with a unique design have significantly declined.

People are far more conscious of the cost of used football shirts, and resellers and larger third-party retailers have increased the prices to reflect the demand. In some cases, legitimate good quality shirts in adult sizes, like the Netherlands kit from their victorious 1988 Euros campaign, can fetch more than £1,000 ($1,300). An authentic USMNT “denim” pattern shirt, worn by the host nation during the 1994 World Cup, regularly demands prices above £500.

Coupled with the increasing prices of contemporary shirts, which typically range from around £60 to £80 for the ‘replica’ version to more than three figures for the ‘player-issue’ versions produced for Premier League clubs, sales of fakes are now on the rise. According to Corsearch, a global leader in trademark and brand protection, the online market for counterfeit football shirts for Premier League clubs has risen to £180million per year.

“In the past two or three years, there have been a lot more fakes knocking about,” says Jack Mcandrew, owner of Sound Trout, an online independent vintage retailer. “It’s due to social media and the influencers who have been wearing football shirts, in some cases even wearing fakes themselves without realising, indirectly increasing the demand and creating opportunity.

“I’ve come across a lot, even from sellers who I know to be reputable. But because the shirts are so in demand and the quality is so high, people fall for them. It’s funny, because the factories that make the fakes aren’t even just doing the ones that are considered cool and coveted, like the Atletico Madrid home shirt from 2004-05 with the Spider-Man kit sponsor, they also do random generic ones.

“I’ve had to be a lot more careful. If a shirt is from the 1990s and it’s in ‘mint’ condition, nine times out of 10 it’s probably too good to be true.”

Authentic USMNT “denim” pattern shirts, worn during the 1994 World Cup, regularly demand prices north of £500 (Ben Radford/Getty Images)

For independent store owners like Mcandrew, the growing counterfeit market means they have to be extra careful when buying shirts from online outlets or inspecting in person at car-boot sales.

Classic Football Shirts, which operates a significantly larger operation with more than 160 employees, has staff responsible for sifting through fakes and procuring legitimate retro classics from all corners of the planet.

“We’ve got a rigorous authentication process,” says Bierton. “This includes looking at labels and product codes and comparing them to shirts we have. We used to have a thick written manual, and now it’s computer-based, but we have a team of around 20-odd people working on the process. It gets more challenging, particularly with the quality of fakes now produced, but once you’ve worked here for a couple of months, you can usually tell the difference.

“It’s still the case that over half the classic shirts are sold to us by people through the website. But there are crazy jobs within the company, basically hunters, whose role is to go out and find shirts in the wild for us. They go around the world, making connections to find old shirts.”

As the trend has popularised, it has become more of an international industry. While there have always been collectors worldwide — Classic Football Shirts sold its first jersey to a Liverpool fan in Norway and has had interest from “hardcore” kit enthusiasts from South Korea since its inception — subcultures have developed reflecting specific interests within populations.

“Particularly in the U.S., many fans are drawn to ‘hero printing’,” says Bierton. “It’s about players as much as teams. I think of the U.S. customers as similar to myself regarding Italian football of the 1990s. I wouldn’t necessarily support any of the teams, but I love the idea.

“I would have a Parma shirt, a Sampdoria shirt, a (Gabriel) Batistuta, (Francesco) Totti or (Roberto) Baggio shirt. That’s the Premier League to a lot of fans from the States. They might like Thierry Henry, Wayne Rooney or Sergio Aguero. They tend to be more interested in the technical aspect in Asia, preferring the player-issue shirts.”

The 1990s remain the golden era for long-time shirt collectors and those who have immersed themselves in the trend more recently. Manchester United and England tops with Beckham’s name printed on the back are among the most popular on Classic Football Shirts, competing with Cristiano Ronaldo and Lionel Messi ones.

With the introduction of ‘icon’ cards on the Ultimate Team mode of the EAFC video game, legends of the era such as Zinedine Zidane and the original, Brazilian Ronaldo have maintained their relevance to younger generations, and their shirts remain some of the most coveted.

Football in 1997 – when players’ shirts were definitely baggier (Alex Livesey/Allsport)

“The ’90s is the high water mark,” says Bierton. “There’s much more freedom of expression in the kits. They’re bolder, and they’re baggy. It’s not ‘Fly Emirates’ on the front of the shirt; it feels pre-commercialisation. It feels like there is still something pure about these shirts.

“There’s something about the 1990s and early noughties that has managed to capture the imagination of younger generations.”

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(Top photos: Getty Images; design: Dan Goldfarb)