Harry Redknapp once told Jermain Defoe that the former Tottenham and England striker would make a "brilliant" manager – now he’s about to find out.
Defoe has thrown himself into his first management role at National League club Woking after working as a player-coach at Rangers and in Spurs' academy.
The 43-year-old has been searching for an opportunity since leaving Tottenham in 2024, picking the brains of Redknapp, Gareth Southgate, Lee Carsley, Robbie Keane and Sam Allardyce on his way to earning his UEFA A license.
But while the likes of his former England team-mates Frank Lampard, Steven Gerrard and Wayne Rooney have landed jobs at the top levels, Defoe, who scored 20 times in 57 appearances for his country, is taking a different route in the fifth tier.
"My mum's always said to me, in life you've got to be grateful for every opportunity you get," said Defoe. "Everyone's journey is different. I've sat down with Lee Carsley and Gareth Southgate and spoken about their journeys in the game.
"You look at [Jurgen] Klopp's journey, when he was forced into management, sort of fell in his lap, Gareth the same. But I think for me, it's important to appreciate the opportunity. And it's no different when you're a player.
"When I was a young 16-year-old at West Ham in the youth team, you have to earn your stripes, you have to do your apprenticeship. You can't expect, just because I've had a good career, to just jump in at the top or get that big job."
Defoe is the Premier League's 10th-highest scorer of all time with 162 goals in 496 appearances and was called up to three major tournaments with England.
He is a League Cup winner at Tottenham and a Scottish Premiership winner at Rangers under Steve Gerrard, yet landing a job in management still hasn't come easily despite interviews at several clubs.
Defoe always believed he would get an opportunity but is under no illusions that, when he takes charge of his first game on Friday against Eastleigh and then his second just three days later at Braintree Town, failure at non-league level would set him back a long way.
"I know there's been a lot of noise around it," said Defoe of his appointment. "There's been some unbelievable messages from players that I've played with, current players and managers and people in the game, which is a nice feeling. But the fact of the matter is, you've got to win football matches.
"I'm going to need help as well. You come in to help a group of players get better and to win games, but a manager also needs help as well.
"I've never played at this level. I know people who have. I've got a lot of friends in the game that have played at this level, who I've had conversations with recently. I've worked with coaches who have played at this level, that I've had conversations with.
"When you love football, when this opportunity came about, it was an easy decision. This is the one that really stood out for me in terms of the project.
"If you speak to any manager, regardless of the league and the standard, it's always going to be a gamble."
Defoe still speaks with his former Tottenham and West Ham boss Redknapp and has visited his former team-mate Keane at Ferencvaros to watch training on his road into management.
He will be assisted by Paul Bracewell, the ex-Stoke, Sunderland and Newcastle midfielder that he worked with at Tottenham's academy. They've all contributed to this moment.
"Lee Carsley was really honest in the conversation about when he first started coaching," said Defoe. "He knew that he had to improve. He had to get good people around him. That's going to help. Especially when it's your first job.
"And also being humble. Being humble is important. Just because you've been a top player, there's no guarantee that you're going to be the best manager in the world and you're going to know everything."
Allardyce, who Defoe played under at Sunderland, messaged him this week to say good luck. He may need it at Woking, who have never been in the EFL in their 139-year history, almost went into administration in July 2024 and have sacked three managers in three years.
The latest to go was Neal Ardley at the beginning of March when a shock defeat in the FA Trophy at Marine followed a string of poor performances and was the breaking point for a frustrated fanbase after two seasons of fighting relegation.
Player-goalkeeping coach Craig Ross and player-fitness coach Jake Hyde bought the club time to find a replacement, leading a revival with four wins and four draws from nine games that has left the club 10th in the National League.
"I messaged Craig last night saying it was great to meet you, a really nice, humble guy," said Defoe.
"He sent a message saying, 'Thanks Gaffer' which was a little bit strange being addressed like that, but I sort of enjoyed it."
Todd Johnson, an American businessman, rescued Woking at the start of 2025 from previous owner Drewe Volpe, who needed a £600,000 loan from his parents to ensure the club could start the 2024/25 season after losing control of the club's spending.
Johnson has implemented a more structured approach by hiring director of football Jody Brown and he will work closely with Defoe over recruitment. Their playing budget, though, is much lower than the former Football League clubs currently sitting at the top end, but that hasn't dented ambitions.
"The main objective is to get promoted," said Defoe. "I believe that me and my coaching staff think that we can go to the next level."
Harry Kewell, Troy Deeney and Edgar Davids are among former top pros to have all tried and failed in the lower leagues. Can Defoe buck the trend?
"Towards the back end of my career, I remember Harry saying to me, 'You've got to go into management, you'll be brilliant. How much you love football and you've always dedicated yourself.'
"This is something that I've always wanted."
