Talking all things football with The Times’ Henry Winter

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This interview was conducted in February 2023 for Palatinate Sport’s upcoming ‘On the Crumb’ magazine.

The ubiquity of Zoom has brought with it a fresh array of etiquette. Gone are the days of the traditional sustained eye contact and firm handshake. Instead, they have been replaced by wry smiles and burgeoning bookcases.

I interviewed Henry Winter, The Times’ Chief Football Writer and a stalwart of the beautiful game’s media coverage, on an overcast Wednesday morning.

More notably, this was the morning after Real Madrid’s night-time, five-goal demolition of Liverpool at Anfield last season; but, looking at the man, you would not have guessed it.

Instead, glaring from the screen before me was a writer ready for action, supported by a hefty bookcase the likes of which would stoke envy in any frequent user of online calls. How could this be anything but daunting?

Nonetheless, my qualms were soon quelled with the topic chosen for our initial conversation: football. Again, how could it be anything but football?

“I’m surprised anyone’s up there!” Winter, joyfully referring to Newcastle United’s upcoming journey to Wembley ahead of that week’s League Cup final, is unexpectedly obsessed with the game. Rightly so.

Such a quality is quite beneficial for someone who reports on matches almost every three days, alongside a series of columns, interviews and features focused solely on the game. My first question, therefore, seems rather obvious. Specifically, I ask what he finds so attractive about being a football journalist.

“I quite enjoyed the idea of travelling the world, I’m quite nosey – if I’m sitting next to someone on the train, I need to know their life story. If you want to be a journalist, you’ve got to have that curiosity.

“I was at school in Paris and Munich for a while, so I just got this appetite. The football scene wasn’t great in Paris when I was a kid. Munich was okay. I actually got Bayern Munich’s one boring season, which was a pity!

“Everything is unscripted in football journalism, and I love that. Yesterday, I knew I was going to the match at Anfield in the evening, but I had a couple of interviews during the day and then you come out of those thinking, ‘honestly that was just so good’ and – not necessarily the research – the interview went well.

“I just love the unpredictability. I couldn’t do a 9-5. I want to be wandering around the world, going to World Cups, meeting people.”

I just love the feeling of being there and possessing that ability to actually convey the drama of the event to people

Thus, this fervent sense for adventure is something that seems to have been conceived during Winter’s childhood. His formative years were mostly spent in London studying at Westminster School, before an eventual arrival at the University of Edinburgh.

However, alongside this relatively lofty education, it was the words of one predecessor at The Times that inspired his dream of entering football journalism. Furthermore, this is something that sticks with the wordsmith to this day and continues to influence his work on a regular basis. 

“It’s something I wanted to do since I was fourteen. In the corner of the house at school there were newspapers, including The Times, and they had this unbelievable writer there, Geoffrey Green, and he’d enjoy going to countries and enjoying himself.

“He wrote one piece which was about a game at the Maracanã and most of the report was about his journey in a taxi from Rio de Janeiro airport to the game. I loved that. I got caught up in the colour of it.

“I’m not a technical expert on football but I just love the feeling of being there and possessing that ability to actually convey the drama of the event to people watching on television and listening on the radio, giving them a scribble of colour.

“He had this famous cottage in Twickenham, and I never went there but some of my older colleagues said it was extraordinary. In his front room he had a Christmas tree with the lights on, blazing away in the middle of June and July.

“Everyone would ask why, and he would say, “when you’re a football journalist, every day is Christmas Day”. In a way he’s right. We’re incredibly privileged to do what we do.

“I also loved playing football. I went to a lot of the London clubs and watched them. Then, I got turned down by Oxbridge. I thought “f*ck them” and went to Edinburgh. They were absolutely brilliant.

“I told them I knew what I would do the day after my final exam, which was go down to a sport agency or Fleet Street and see if I could blag my way in there.

“I was Sport Editor at The Student (Edinburgh’s student newspaper), but obviously every year we were very aware of the quality of Palatinate and the quality of their production. Now Mark Pougatch is a mate of mine!”

Possessing the desire to make it in the world of football journalism is one thing. Nevertheless, regardless of one’s background, getting there is another. For Winter, the beginning of his retrospectively successful career was far from rosy.

“I kind of stumbled into it. It was always going to be a passion, but the actual logistics were something else. People think it’s always a smooth career, but it’s not.

“I got turned down by loads of places – BBC, ITN, all people like that – and then just managed to convince one person to take me on and plug phones in at Luton Town.

“When I started out there weren’t that many football writing jobs, whereas now you look at The Athletic and inhouse jobs at football clubs, here and abroad. Just look at the media teams at League Two clubs. It used to be the kitman when I started out!

“Your generation is fortunate, and you’re all so good with technology! There are so many things you can do yourself as well. It’s fantastic. Mobile phones are great – I can write an 800-word report on it with steam coming out of my thumbs!”

Henry Winter is often The Times main writer for all major football matches. (Image: Victoria Bowland)
Image: Victoria Bowland

Now seemingly at the pinnacle of his profession, Winter is subject to what one would typically perceive to be a tiring routine. With matches in today’s version of the game coming thick and fast, and barely a day or night free from the grappling hooks of football, it would be easy to expect some form of jading to appear in the fingers and minds of someone such as himself.

Yet, Winter’s relaxed but enthusiastic approach ensures that no such inhibitions creep into his efforts. They are instead replaced by a sense of self-consciousness and enlightened perspective.

“It’s not work. I have mates who are surgeons and pilots. If they make a mistake, they have to bury someone. If I make a mistake, I might get sued. That’s only happened one and a half times, and I didn’t have to pay out, fortunately!

“It’s a privilege to go to the World Cup and have that platform and write about the social issues involved. When I started out, I would just write about heads and volleys. Now, I will talk to Amnesty International, talk to Kick It Out.

“There is that thread running through your copy now and that is a privilege. At the heart of it has to be 90 minutes of the game, but also the fans. It’s also writing about issues in life, and I think that is one of the great privileges of this job.”

Away from the pitch itself, Winter is also a frequenter of several training grounds around the country. This is not due to an irrepressible desire to spy on each club’s weekday preparations, but instead to sit down and chat with the greatest and most notable figures in football as he seeks to provide an insight into their lives and backgrounds.

Whilst discussing this topic, it soon becomes evident that Winter views this as an integral aspect of his job, riddled with key techniques and a determination to garner the best story possible.

“You have to know more about them they do themselves, if that is possible. You just immerse yourself in everything. It’s slightly easier nowadays, particularly with social media.

“I interviewed a player yesterday and I went through his feed to know everything about him. Your generation, which is helpful, is far more expressive – everything is out there. Footballers get interviewed by loads of different people, and you want to get something different out of them.

“I always try to take them out of a football environment if it’s possible, either over Zoom or at the training ground.”

Following this, I ask how Winter handles the daunting prospect of chatting with the superstars we see so often on our multitude of screens and read about so regularly in the news. As is his kindly way, this leads to his sharing of the wisdom that has led the man to his current position as one of the few heads of football journalism in this country.

Accordingly, such advice is also filled with scintillating stories.

“Don’t be daunted. You are in that room with them because you love football as much as they love football.

“What I do is I don’t take any notes with me into an interview. I just take two tape recorders – never one because I lost half an Ashley Cole interview once! I put them discreetly down and then no notes. I had one footballer who picked up my notes and said, “that’s a crap question, we’ll start with another one”. I want it to be more of a conversation.

“I interviewed one FA Chairman, and it was about the status of English football and the only time he could see me was during a break in the division at the House of Lords. So, I went in to see him and we went into one of the tearooms. I took out my tape recorder and he told me to put it away.

“In a very British way, he ordered some cucumber sandwiches and he made a nest for the two tape recorders and we carried on that way without the guards watching us!”

Life’s not about being daunted. It’s about seizing it

After this brief but exciting digression, Winter returns to the central aspect of his advice for aspiring football journalists.

“It’s a conversation between equals, so never be daunted. They’re very fortunate to do what they do and a majority of them appreciate that and want to get their story out there.

“Life’s not about being daunted. It’s about seizing it.”

Soon enough, it was time to turn to a topic that is almost always on the prints bearing Winter’s name during the traditional off-season: the England national team.

Having covered nine World Cups and seen a range of generations come through the national setup, I begin this line of questioning by discussing the current crop looking to lead the Three Lions to success on the international stage.

“Every generation has its own strengths, but the current one’s shirts don’t hang heavily on them. Look at Bukayo Saka and the disgraceful racist abuse he received after the final.

“In the past, one or two players might have said they’d never want to play for England again. We had that with one player in Portugal who wanted to stay away and escape the abuse.

I think this is a pretty resilient bunch of players. Look at how Jadon Sancho is coming back, look at Marcus Rashford – he’s a sensitive, thoughtful individual but he’s also tough – and Saka takes penalties for Arsenal in big pressure games, and he’ll take that responsibility.

“There are so many good, young players coming through.

“That is one of my issues with Gareth Southgate. I’m looking at this generation and I wrote quite an ‘angry’ piece ay the end of the World Cup when everyone was congratulating them for getting to the quarters. I was saying we had to be angry. This generation has got a trophy in them, and I want to see them fulfil that potential.”

For Winter, therefore, it is obvious that the point of distinction for this generation is its ability to develop a culture which no longer attracts the toxicity of its predecessors.

“With the golden generation, you saw the players who came along, put the shirt on and were always inhibited. We used to joke with the players and ask them to put their club shirts underneath as it might embolden them.

“In a way, whatever their form is like with their clubs (for this generation), England is like a family to them. They’re all in it together. And Southgate, despite his game management, has changed the culture of England.

“The shirt doesn’t hang heavy anymore. He knows because he was part of that as a player.”

Nonetheless, the discussion does not end there. As aforementioned, in the aftermath of the Qatar World Cup Winter wrote a passionate piece focusing on the falling points of England’s Quarter-Final defeat to eventual runners up France.

I thus ask him what inspired the piece, and what more can be done by those surrounding the national team.

“I think Southgate got it very easy after that. If he goes and wins the Euros in Germany (in 2024), that will be wonderful. But, he’s got to win at the Euros with this generation of players, with (Jude) Bellingham and players like him.

“They can’t waste this generation of players. They’re just too precious, just too good, and they’ve got a trophy in them and that’s why there’s a little bit of anger. That anger was also slightly aimed at the FA.

“I’ve had a meeting with them since as they were angry with the piece, and I said they should be angry. There’s nothing wrong with anger.

“Do you think Sir Alex Ferguson would have been happy with that? He would’ve been straight back in his office with steam coming out of his ears, working out how to fix it.

“There seems to be a little bit of a love in with England at the moment. Maybe because I’m one of the older journalists I’m not completely at ease with that.”

Despite his protestations against the current regime, such a stance derives from a sentiment of passion, not immovable hatred.

“I just want to see them win. I’ve seen near misses before. I know this generation have a trophy in them.

“I love Southgate’s style of ‘love the sport, hate the industry’ and I just think nice people don’t always finish first – but then Carlo Ancelotti shows that maybe it can happen.

“I just hope the gods smile on Southgate.”

(Image: Riyaad Minty via Flickr)

For anyone who has attempted to write a match report concerning a side with which they possess a sense of partisanship, it is perhaps rather easy to allow such feelings to enter the realm of written word.

So, with Winter’s regular coverage of the Three Lions, I ask how he manages to maintain some element of impartiality, especially when the larger occasions arise.

“I think it’s quite straightforward to juggle writing with your head and with your heart. The best writers have got this ability to write with passion and perspective. Anyone can swan off to their ivory tower, with jazz on in the background and spend four or five hours drafting a piece.

“The daily beat journalists, multi-gifted writers, do it against the clock. I love that idea of working against the clock. That’s why I could never write for a Sunday newspaper. They’ve got that ability to stand by the ring and take in the whole occasion as well. That’s such a difficult thing to do.

“I would say: the bigger occasion, the more you should write with your heart. You can talk about all the tactics. I want to walk out of that ground afterwards feeling that I’ve thrown everything at that piece.

“Passionate and dispassionate: if you can mix them up, then you’re a high-speed Mantovani.”

Another feature of Winter’s illustrious career has been his tendency to ghost write some of the biggest football autobiographies of this century for the likes of Steven Gerrard, Kenny Dalglish and John Barnes. Alongside this, he has also produced ‘Fifty Years of Hurt’ which documents England’s fall from grace following the World Cup triumph of 1966.  

This role, he makes obvious, has been one of privilege and unparalleled experience.

“It was brilliant because so much of this job is a privilege. I mean, sitting down and spending time with Kenny Dalglish and writing two books with him – one more and he gets to keep me! That was fascinating.

“You don’t do it for the money. Whatever you do in life, you don’t do it for the money. It’s all about the passion for your job and getting to the top. The money is a secondary, tertiary thing you know.

“So, when you do books like that, they’re not particularly well paid, but they’re just such an enriching experience. I’ve sat with Kenny and watched a match, and he was saying “a substitution will be made there” and two minutes later the managers made it.

“You just think, “this is such an education, this is just gold dust”. It’s such a privilege.

Then there are the more current ones – sitting with Steven Gerrard. I come from a sort of nice fluffy London background and actually seeing what people like Gerrard went through and how he fought his way to the top was quite an education.

“John Barnes was another, and we’re a similar age. He came across with his father, who was a military attaché at the Jamaican embassy in London, but we knew the same sort of areas and I went to the same shops as him in London around the same time and I would have the doorman opening the door for me.

“He would have doorman say he can’t come in because they were worried he was going to steal something because he was black and in a Watford tracksuit.

“You’re doing it because you want to do a good job for them. You want to help them tell their story. But I also find it incredibly educational and enlightening. I learnt more about life. I learnt more about people. I learnt how to vicariously understand what people have gone through.”

This implicit psychoanalysis also allowed Winter to ascertain what makes a winner and how their dogged mentality is constructed.

“I’ve found with these high achievers; they’ve all got a pebble in their shoe that rubs away at them. Ferguson, for example, is brilliant in defeat.

“I would mainly go to Ferguson’s press conference after a loss because there would likely be verbal fireworks. He would blame the kit, the weather, the referee, the media, would say that the stars weren’t aligned. Anything but his players, and I loved that.

“I don’t think there’s anything wrong with having a grudge. You saw it in ‘The Last Dance’. People almost create a narrative just to drive them on. I love that.”

It was clear to see that Winter possesses – alongside his bursting bookcase – an unrivalled love for the game. Throughout the spellbinding interview, an urge to break forth from the dulling formalities of the discussion and simply ‘talk football’ eventually became irrepressible.

Soon enough, we were chatting away in a fashion that would not have been out of place in the stands of any stadium across the country. I suppose, in retrospect, it was impossible to truly be daunted. It’s just football, after all.

Featured image: @henrywinter on Twitter/X

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