Breaking Into Football Writing and Media: Insights from Henry Winter

Hi Henry, thank you for taking the time to speak with us today. I’m certain most people reading this know who you are, but for those who don’t, can you tell us a bit about yourself and how you got to where you are?

Hi, I started out at the sports agency Hayters in 85, then the Indy in 86, Telegraph in 94 and Times in 2015.

I left the Times in April 2023, and now enjoying the broader options in the media, including radio (BBC and my own show on talkSPORT), TV (Sky Sports News, LFCTV, BBC News etc), film (‘Moment of Truth’ for Sony), books (one just finished, 70,000 words into the next) and loads of social media. I also have my own Substack with 10,000 subscribers.

What inspired you to pursue a career in sports journalism, and how did you land your first job in the industry?

I always wanted to be a football writer because of love of the game, writing and travelling and I didn’t fancy working for a living. Football writing is not work, it’s a privilege.

I was inspired by a football writer called Geoffrey Greene who wrote a famous match report from Maracana mainly on his journey from Rio airport. At university, I explained to my tutors I was there to write for the student newspaper on sport, to play football and scrape a degree. And they let me. The day after my final exam, I went and knocked on the door of Hayters sports agency off Fleet Street.

What key advice would you give to aspiring sports journalists trying to break into the industry?

Trust. It’s key. It takes years to build up a reputation and seconds to lose. If it’s got your byline on it, take control also of the headline. Ask them to change it. Don’t be associated with clickbait.

What’s one skill you think is underrated in journalism?

Listening. I get punters come up to me, wanting a chat, and I immediately flip it, and grill them, so I come out of the exchange with knowledge. Their views on their team, on the game. Just listen.

As our focus is on supporting freelancers in the football media landscape, we believe our newsletter is an excellent resource for finding work. Are there any specific tips you can share with people looking to gain more work?

Use social media. Pretty obvious but post and link. And if you’re emailing a sports editor, find out their team and start your email with sorry Villa/City/Chelsea lost last night.

Are there any interviews or projects that stand out as particularly impactful in your career, perhaps those that elevated your career early on?

I’ve probably done 1,000+ football interviews, and the most important one is always the next. But I guess doing pieces with Marcus Rashford on child food poverty, Chris Kirkland on footballers’ addiction to painkillers and Raheem Sterling on racism stand out because of their broader impact.

Can you share some insights into your writing process?

Yes but it’s a bit rude. Basically I start every piece thinking the first words should have the same resonance of “F*ck said the duchess”. That immediately engages the reader. Why is the duchess swearing, who is the duchess, what is going on? It makes you read on. Your opening line to any blog, article, radio show is your shop window to draw people in. Don’t give me dry facts and stats in the opening par. Grab me with some drama and I might stay for the rest of the article, some of which further down will have the facts and stats etc.

After your time at The Times, you started ‘Henry Winter’s Goal Posts’ on Substack. What motivated you to start your own newsletter?

I love writing. It’s a small but fun part of the day. Basically, more and more sports writers are leaving newspapers and setting up on their own. The trend (and substack) began in the States where big-name sports writers decided to go it alone because they had a big following.

Can you share any useful tools or resources that you find helpful to fulfil your role?

I don’t need much sleep! Five hours’ a night is fine plus I have a meditation trick to give me a 5-minute top-up in the afternoon.

Knowing what you know now, what advice would you give to your younger self if you were starting your career today?

Work hard and be nice to people. It’s obvious, and I hope I’ve always done that. But worth remembering that being polite, and chatting to the receptionist or an academy coach at a club, is 1, the right thing to do and 2, they might rise up the scale and prove really important. One receptionist at the Premier League who I always got on with became a club player liaison officer sorting interviews.

Remember that athletes/stars etc are humans, too. Their parents will be reading your piece? Will they recognise their offspring. Do interviews away from sporting settings (training grounds etc), take them back to school. I went back to Rashford’s old primary school with him last month — he was handing out presents — and, to my slight surprise, got a news story out of it.

And finally, Henry, what do you do to switch off outside of work?

I don’t work! I don’t need to switch off! But for everybody reading this make sure whatever you write about you do it with a passion. Because it’s more enjoyable and your readers/listeners/viewers will be more engaged. And remember there’s no such thing as luck — the people I’ve met who’ve got to the top of sports writing, and the elite footballers I’ve interviewed, have all got there through hard work as much as talent.

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