Henry Winter is launching a paid-for newsletter on Substack as the new home of his journalism after being made redundant from The Times.
Winter told Press Gazette he was “itching to write about football again, because it doesn’t leave your blood” and as a result he soft launched last week and officially goes live today (Monday).
He plans to put out a newsletter at around 9-10am each weekday morning (having got up at 5.30am). The Monday newsletter will be free and the rest of the week will be for paying subscribers only.
Winter is promising “news, views and interviews” both in written, audio and video form, saying he knows it is “important to evolve” even after a near 40-year career in journalism.
He described his goal for himself to be a “very unathletic decathlete” in terms of mixing mediums. He is also writing a book, makes frequent radio appearances and has more than one million followers on Twitter/X.
Winter, who previously spent 21 years at The Daily Telegraph, announced earlier this month that he had been made redundant from The Times, where he has been chief football writer since 2015. He is the incumbent Football Journalist of the Year at the British Sports Journalism Awards.
He told Press Gazette he had “no regrets” and it had been his dream to work at The Times since he was about 15.
“I respect them so much and I can say what a wonderful time I had there, eight great years. They gave me a platform to go to Ukraine, to go to tournaments, to leave with a couple of trophies, and it was a dream to work there.
“So I was lucky to fulfil my dream, obviously disappointed to go but touched by the reaction on social media.”
Speaking on Friday, just over a week after announcing his departure, Winter said he has had a “lovely” reaction from all 20 Premier League clubs, many clubs in the English Football League, football associations and others.
He therefore still hopes to be able to attend some games and put out match reports on his Substack, although a lot of what he will be doing will be “about the issues of the game and interviews”.
“I’m certainly going to the Euros,” he added. “I’m not staying in a nice hotel where all the boys are staying, I’ll be in an Airbnb around the corner, but the important thing is to go to the games.”
Winter, who back in 2010 was voted Britain’s top sports journalist in a Press Gazette poll, also said some players have been in touch and said they would be happy to do something with him on Substack.
“That’s where I’ve got to become cuter and do some of it as video and do some of it as audio, and just mix all those up together – coming back to the decathlete element.”
Why Henry Winter is setting up shop at Substack
Winter’s launch comes almost exactly a year after fellow former Times writer, columnist David Aaronovitch, went live with his own Substack, which now has more than 13,000 subscribers.
Winter revealed he was first approached by the Substack team about three years ago but he “loved The Times so I wasn’t going to leave”.
However he has followed how other sports journalists have used the platform: “America’s obviously ahead of us on a lot of things and you look at how Substack’s used in America by sports writers, you look at the baseball writers, basketball writers and some of them have left, obviously their decision, some major American publications and set up on their own,” he said. “They’ve got huge followings.
“So there’s a market out there and better writers than me, say like Jamie Jackson at the Observer/Guardian, he’s their Manchester man – he’s on Substack and he’s really good on it but he’s a bit more so technologically sophisticated and design orientated than me.”
Winter said he had also been inspired by Grant Wahl, the American soccer journalist who left Sports Illustrated in 2020 to launch his own podcast and newsletter on Substack. Wahl died suddenly aged 48 in December 2022 while covering a World Cup match in Qatar.
“He’s been a role model for me in many ways as a man, as a football journalist, but also in the way he approached new media like that,” Winter said.
Industry ‘fracturing’ but everyone needs same skill: Storytelling
Winter, who began covering football in the 1985/86 season and remembers knocking on people’s doors asking to use their phone so he could dictate his copy down the phone, said the biggest change in his career has been the arrival of Wi-Fi and the iPhone, which has meant citizen journalists are “almost the first draft of history now as much as us”.
Last week Guardian sports writer Jonathan Liew wrote that Winter’s surprise exit from The Times was a sign of how football “has been fracturing for years: attention and influence draining away not just from traditional newspapers, but from everybody… What once constituted our shared football space has splintered into a million galaxies: forums and fan media, podcasts and Youtube channels, blogs and specialist websites, Reddit and Tiktok, the curated feeds that allow us to view a game through whatever filter we choose: tribal, social, banter, fantasy team.”
Winter told Press Gazette in response that there was “definitely a lot of truth in the fracturing” but he viewed everyone as having “the same skill, it’s storytelling, and whether you’re doing it in 100,000 words, and you’ve taken two years to tell that story in hardback version, or whether you’re doing it down the line adlibbing something from a football match or whether you’re doing it on a podcast, or whether you’re doing as a tweet and there’s that immediacy, I still think it’s the same skill of storytelling.”
Asked whether it showed a decreasing influence of and appetite for content from legacy titles, Winter disagreed and cited several “brilliant” journalists from the likes of The Times, The Telegraph and The Guardian.
He said: “If they put a story out on social media, everyone knows it’s 100% correct. There’s absolute trust for them. So, in a way, everyone sort of says, oh, there’s a media wild west on social media, but actually, it’s highlighted the people who are genuinely in the know…”
He compared it to the boost in subscriptions at titles like The Times during the Covid-19 pandemic: “I still think people aren’t stupid and they know who they can trust.”
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