“It’s been a long time coming,” Jermain Defoe says on his first day as Woking’s manager. Dressed in a sharp grey suit that he admits he is wearing on the instructions of his mother, Sandra – “I know she’ll be watching this, and she’ll be like: ‘You’ve got to look smart!’” – the former England striker certainly looks the part as he fields questions in the unassuming surroundings of the Cardinal Bar at the Laithwaite Community Stadium.
From missing the buzz of playing top‑level football since retiring in 2022 to acknowledging why it is crucial to “earn your stripes” as a manager, Defoe is brutally honest about the task that awaits him at the club that has never made it to the Football League in 139 years of existence. He even jokes that he turned down his former team Tottenham to take over at Woking.
Defoe, who had a spell as Steven Gerrard’s assistant while playing at Rangers, spent two years in the Spurs academy working with the under-18 and under-21 sides before leaving in July 2024 after being told there was no role with the first team, then managed by Ange Postecoglou. He has since been on the lookout for his first opportunity as a head coach, although it took almost two years until Woking’s director of football, Jody Brown, came calling when looking to replace Neal Ardley at the mid‑table National League side.
“I didn’t ever think: ‘It’s not going to come and I’m just going to give up,’” Defoe says. “I’ve never really been like that, to be honest. I think you always have to remain positive. When you do all your hard work, that’s all I could do really. All I could do is finish my badges and then just hopefully the opportunity will come. I’ve had loads of conversations with clubs, so it was always getting close. And I knew it would come at some point. But in football, you just never know what’s around the corner.”
If one word crops up more than any other during his press conference then it is “grateful”, another lesson the man who won 57 England caps and scored more than 300 goals over a 23-year career learned from his mother. “She has always said to appreciate the opportunity,” he says. “It’s no different than when you’re a player.
“When I was a 16-year-old at West Ham in the youth team, you have to earn your stripes, you have to do your apprenticeship. Just because I’ve had a good career, I can’t expect to just jump in at the top or get that big job. It’s one I’m really looking forward to.”
The fact that Defoe is only the fifth black manager or head coach working in English football’s top five divisions is an indication of the battle he has faced. “It’s something that’s been spoken about for many years,” he says. “I remember as a player, obviously all the different campaigns. Speaking to the likes of Les Ferdinand, Ian Wright, Andy Cole. That sort of generation before me who did their coaching badges and obviously [there was] a lack of opportunity. I’m so grateful for the opportunity but I’d like to think going forward that other black managers will get them, too.”
Does it place more pressure on him to be successful? “There’s always going to be expectation on any manager at any level. The expectation you put on yourself.”
Defoe is itching to get back out on the grass again after watching Woking’s draw with Altrincham on Tuesday evening from the directors’ box, with Eastleigh his first opponents in a Good Friday home game.
“I still get that same feeling,” he says. “I remember as a young kid, that feeling you get in the morning before a game. It’s the same with coaching: putting your boots on and planning the session, delivering the session and then going into the game, and you can see the patterns that you’ve worked on, and actually winning football matches. There’s nothing like it. For me, the love for football’s never changed.”
Promotion is the target next season, and Defoe, who never played at this level, is hoping the vast experience of his assistant Paul Bracewell – the former Everton midfielder with whom he worked at Sunderland and Tottenham – will help the process of settling into life in deepest Surrey. “He keeps reminding me of the trophies that he’s won,” Defoe says. “He’s had 35 years in the game so he’s priceless.”
Sam Allardyce and Harry Redknapp are among the former managers to have been in touch since his appointment, and Defoe plans to draw on their experience as his career progresses. But no prizes for guessing who has been the most influential person in his career.
“My mum knows that this is something that I’ve waited a long time for so she has said I have to make sure that I enjoy it. I think it’s important to have those kind of influences in your life because those are the people that love you.
“I’m sure there will be constructive criticism, because it’s your mum and you have got to take it on the chin. Even at the age of 43 that is still the person that I want to make proud.”
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