Sports journalism king Henry Winter’s tale

Henry Winter is renowned as one of the contemporary greats of football journalism, an established titan of Fleet Street in all its guises.

After graduating from university, where he edited the weekly sports paper, writing about football was all he wanted to do.

He joined Hayters, the breeding ground for great sports reporters in the UK, led by the legendary Reg Hayter, who shaped the culture of sports journalism.

“He was quite formidable character,” says Henry. “And he got me working on one or two publications, and I was useless. They quite rightly got rid of me, so I went and did a quick course and then fortuitously the Independent started up. I had eight great years there, learning under amazing sports editors Charlie Burgess and Simon Kelner.”

Henry would join the Daily Telegraph in 1994 and then The Times in 2015 where he became Chief Football Writer until he was made redundant in 2024, the year he was awarded Football Journalist of the Year at the British Sports Journalism Awards.

A regular commentator on radio and television, he has also written a number of books and even films, proving that a career in football journalism could provide the opportunities and the prestige that may not have been obvious in the mid-1980s.

He recalls “Coming out of university, all my mates were going into politics, law, banking, what my parents would call proper jobs, and they said, ‘What are you doing in football?’

“It was months after Heysel (where Liverpool and Juventus fans clashed before the 1985 European Cup final, resulting in 39 deaths and many more injured. England were subsequently banned from European football as a consequence.) and there was hooliganism, there'd be punch-ups and violence.

“You'd be sitting in decaying grounds and decaying press boxes and it wasn't an obvious career choice at the time. But then I even see journalism as a profession, I see it as a passion.”

Much has changed since Henry’s early days, asking for or managing phone lines so reporters could dictate their reports to copy-takers, fixing phones for the likes of John Motson in Italy to the modern era where the biggest challenge is now checking the wifi password and the fractured evolution of new forms of media, such as fan channels, online-only news platforms and various iterations of social media.

Throughout his career, Henry has had access to the biggest names in the game, building a reputation for respect and reverence that requires collaboration with PR and communications staff at clubs and federations.

Unlike many, he is well aware that being a great journalist is very different to working on the other side of the fence.

He said: “I occasionally talk to other journalists who think, ‘Oh I might step into PR.’ It is quite a substantial step and a different skill set, not simply the concept of stopping stories, because good PRs don't do that. They will shape them and mould them and maybe soften the headline or provide some sort of balance, or an explanation or clarification.

“There are some unbelievable PR people out there, really good seasoned practitioners, and it's no surprise that politicians often look at football PRs and think well, if you can handle the fast moving chaos in sport, you can absolutely deal with politics.

“If you've been doing it a long time, PRs often become friends, and I think there's a there's a respect there for the good ones. I get on with the PRs at the clubs. The thing is that we all like football, so we might have a falling out over the depiction of one of their clients in a story, or whatever, but then we'll get back to ‘Oh, did you see that trick he did the other day?’ So there's always that you've always got that in common.

“Good PRs represent their clients and their clubs well, but they're also honest and they're like a critical friend. If I was a player, I would have a good lawyer and a good PR, which is absolute gold dust.

“I do the media training on the pro license at St. George's Park. We have recently had Jack Wilshire, Lee Cattermole and Phil Jones, really good up and coming coaches. We stage these mock press conferences and grill them, and it will be far more intense scrutiny and scenarios that they will probably ever experience unless they become England coach.

“One of the things they all say is ‘have you got any sort of advice?’ I said, ‘Well, if you're under pressure, look at where you're sitting and make sure there isn't an exit sign behind you, or a fire extinguisher, because that's great copy for my intro, and it's meat and drink to photographers. Also make sure your club, or if you're a national team, the National Association, has a good PR.

“I always reference Andy Walker (Senior Communications Manager for England at The Football Association) in the room. He's calm, he knows what's coming, and if you talk to the best PRs, they will walk into a post-match press conference or pre-match press conference with a list of maybe the six or seven subjects that are going to be asked.

“You look at the PR and the manager or the player being interviewed, and they will swap glances, and it's almost like they're playing Question Bingo, because the good ones will have predicted in advance all the questions, and just make sure there are no pitfalls.

“I can't name the manager, but he said something ridiculous about playing a German team, and he made a reference to Hitler. That's not going to work well on a back page, or front page, or online, or wherever. After this manager has said it, the PR would just walk back into the room and say ‘Listen, easy on the Adolf line’. And because you got a respect for him, and also a respect for the manager, no one used it. and that is the power of a good PR. They are worth their weight in gold.”

That bond of trust doesn’t always work, though, with clubs often trying to control a message by scooping the media with their own take on a story.

Henry added: “Sometimes you go to PRs to say we're about to run this story and then at 6 o'clock, or whatever the club would put a statement out or a spoiler and you wonder why on earth you rang in advance. Why did I tip you off? You would instantly lose respect and trust.

“I probably failed miserably, but my parents always said, work hard and be nice to everyone, because, particularly in the fast moving industry like football, someone who can be a receptionist at a training ground one day, and this definitely happened, is running the PR. Players have become a deputy Chief Executive five seasons later.”

Henry has seen the evolution of footballers from a reputation for womanising, heavy drinking and mischief to trying to make a difference in the world, with England forward Marcus Rashford one of the most prominent activists playing the game presently.

Henry added: “I think footballers have always had a conscience, but I think you just see it more now. It's easier to see more now because they've got platforms. So if Marcus Rashford wants to take on Boris Johnson over child food poverty, and making sure that the kids who are going into schools and going into classes and trying to learn do it on a full stomach, that just seems a sensible thing to do.

“I was talking to Downing Street during that period, and I was saying just seriously, don't take on a young footballer with a conscience who remembered his mother, Mel, crying herself to sleep at night because she was worried that when she woke up in the morning that she didn't have enough food in the house.

“Raheem Sterling's Instagram message the day after the game when City were playing at Stamford Bridge, we know that players are still horrifically being racially abused, even in the 21st century.

“I rang up the sports editor and I said that this really does change a lot, the power of this message. We have to be more accountable. There was this depiction of young black players compared to the depiction of young white players.

“What is interesting is that it's developed a stage further, because there would always be that element where the clubs want to keep sort of content for their own. You look at the expanding media operations, particularly the elite clubs, doing amazing video, amazing content for social media. It's absolutely brilliant what they do.

“But the players now have moved on from that. Have a look in the England dressing room. There's some really impressive individuals in there, Harry Kane, the work that he's done on London playing fields, so that the places where he grew up playing in Leytonstone….that are the lungs of the city, and they're the pathways for England players of the future.

“Jordan Henderson gets a bit of stick because he went out to Saudi, having been a campaigner for gay rights. But I can remember calling Jordan during Lockdown, and he would be on his running machine taking calls, organising the Players Together campaign with Mark Noble and Troy Deeney and Kevin de Bruyne, and it was brilliant.

“There were footballers getting hammered by one or two politicians, and they were going out there and raising money and there was no PR on their part. You could just see what they were trying to do, and you could see what the country needed. And you know, maybe I'm a bit soft on footballers, but I actually thought well, fair play to them. So they've got the platform, but the most important thing is they've got the drive. I have huge admiration for them. “

Winter still appears on broadcast channels and has his own podcast as well as a Substack platform where he shares daily insights into the beautiful game.

He reflects: “I've still got ink in my veins, and always have. But I've never considered myself a newspaper journalist

“I'm very bad at looking back. I'm always looking forward. It's all about next opportunity. Next book, next job, next match. I've always been a PR for sport, maybe because the world I grew up in, sitting alongside people at dinner parties slaughtering football. I've always stood up for football, because I've always felt an attack on football is an attack on me. I want to represent the sport that I love which has brought me such joy.”