Sport’s first super agent Jon Holmes on negotiating, mentoring and retiring

First Brian Clough kicked him in the leg, saying: “Who are you?” Then he offered him a plastic carrier bag full of banknotes to smooth Peter Shilton’s move from Stoke City to Nottingham Forest.

It was a mere coincidence that the godfather of British sports agents, Jon Holmes, announced his retirement with this Observer Sport interview in the same week Chelsea were fined £10.75m for making secret payments under Roman Abramovich’s ownership. Holmes remembers looking at the bag of loot and telling Clough, the Forest manager: “We don’t do things like that. I’m sorry, we don’t.”

Described as the first super-agent and the last of the gentleman intermediaries, Holmes, now 75, has never had a contract with any of his stars, despite handling Shilton, Gary Lineker, David Gower, Will Carling (for a while), Michael Atherton and many others, including the barrister and former MP Anna Soubry (“She’s a friend of mine, she used to go to the same boozer as me in Nottingham”).

In nearly 50 years of playing negotiator, mentor and firefighter, Holmes has had to deal with Carling calling the Rugby Football Union committee “57 old farts”, Gower buzzing over an England game against Queensland in 1991 in a Tiger Moth biplane, and Lineker leaving the BBC over his social media posts.

Critically or supportively, Holmes talked to them all straight: “Someone once said to me, ‘You knew when to give me a kick up the arse.’ But you have to do it with a grin at the end. I remember Gower saying to me, ‘If you talked to [Ian] Botham like you talk to me, he would hit you.’

“Players would come to me and say, ‘The manager’s got it in for me.’ And I’d say, ‘Why?’ They’d say: ‘He just has.’ And I would say, ‘Well, it wouldn’t be anything to do with the fact you missed training, would it?’”

What did he say, then, to Gower about the Tiger Moth prank? “The same thing I said to him about putting the car in the lake [when Gower’s car dropped through the ice at St Moritz],” Holmes says. “They [the authorities] were going berserk – talking about taking him off the tour. He’d got two hundreds. He was in prime form. On the kangaroo court, Allan Lamb, who was meant to be the vice-captain, was pissing himself.”

After Gower smashed down his stumps in anger one day, he asked Holmes what he had made of the outburst. “I said I thought it was quite good really,” Holmes says. “He said, ‘What do you mean?’ I said, ‘I never knew you cared.’ He then twigged. He realised he’d been walking around like Percy Fender [a colourful 19th century cricketer]. But he did care. He really cared. There were times when you had to break through the veneer.

“The night before he got his first England hundred [at The Oval in 1978] I took him out for a meal. I told him: ‘You get fifties, you don’t get hundreds. You need to get a hundred.’ The next day he did.”

For half a century, Holmes has been Britain’s link to the invention of sports agents by Mark McCormack, the founder of International Management Group (IMG). Holmes was a news journalist on the Leicester Mercury who read McCormack’s book on the golfer Arnold Palmer – who pioneered the athlete as a global brand.

“McCormack wanted to do do-it-for-me [individual sports] – golf, tennis. I liked team sports.” Holmes says. “What he really understood was the relationship between television, sport and business. In that, he was completely right.”

Back then there was no shark pool of fixers. “There was a guy called Ken Adam, who hung around the Chelsea boys. There was Ken Stanley, who looked after Besty [George Best], in a sort of way. And there was another guy called Ken Johnson, who looked like a Butlins entertainment officer. But there was no one, really.”

In this world of Kens, Shilton gave Holmes his breakthrough – and his baptism, when the England goalkeeper moved to Forest in September 1977, at a time when players mostly dealt directly with club secretaries and chairmen.

“Peter was brilliant. He would say to people – well, if you don’t talk to him, you don’t talk to me.”

Shilton had a lavish contract at Stoke, who had been relegated. “We did a hell of a deal with Stoke. Inflation clauses and Christ knows what,” Holmes says. “At that point Clough wasn’t nasty, he was funny. It was about power with him. He kept us waiting. Then when he came in, the kicking me was all orchestrated: ‘Who are you?’ I was young, so he was going to frighten me.”

The talks dragged on. Clough went out and came back with the bag of readies. Holmes demurred. “In the middle of all this he said to me, ‘Right, outside.’ He’s got his squash racket in his hand. He says: ‘What do you want, son?’

“I said, ‘You know what we want.’ He said, ‘No, you misunderstand me. What do you want?’ Clearly, he was going to bribe me. It was all called off. That was the Friday. Then, on the Saturday, Clough announced the deal had been done.

“I rang Peter and asked what the hell’s going on. And Peter said: ‘I haven’t spoken to him. He’s just announced it.’ Shilton joined Forest and won the league title and two European Cups there.”

But it’s Lineker, who now co-owns his own media empire, Goalhanger, who defines Holmes’s role in the business of sport. Holmes struck his last football transfer deal 20-odd years ago, “because I got old and the business moved on. I’d done with players what I wanted to do. I couldn’t do any more than I’d done with Gary, could I?”

(In the football transfer trade Holmes left behind, English clubs paid £280.1m to agents in 2025. Worldwide the figure was £1.3bn. Those sums are regarded by many in the game as scandalously high.)

“Gary became the top-paid player in England, then he moved to Barcelona and Japan. I enjoyed all that. I was never going to be able to do that again. At one point I had England captains in three different team sports. I had Atherton, Lineker and Carling at the same time.

“As an agent all you do is push people on, or slow people down. They’re going to get there. Gary is a great learner. At his first Leicester game I said to my father, ‘Where the bloody hell did we get him from?’ He fell over the whole time.”

In football, playing golf and broadcasting, Holmes says, Lineker “got better, and watched people, and learned. He’s a student, and he will be learning all the time. He does read up about subjects. I would always say to him – don’t retweet other people’s pieces. You need to say it. But he’s competing then with people of enormous learning. The politicians all got overheated. And I would say to those politicians – what are you so frightened of?”

His main focus since he stopped moving players around has been finding them media careers. When ex-pros arrive in studios, he says, “the people around you will be supportive, but a lot of them think you’ve pinched their mate’s job”. There used to be hostility to players taking jobs in journalism but no longer. “Atherton’s one of the best-read men. You go to meet him and he’s got some gigantic volume under his arm which he’s actually read.”

Sometimes the opposition in talks threw Holmes an easy win. In 1985 Lineker was offered a sum by Everton to sign from Leicester. Holmes asked for a “breather” and took his client outside. Lineker said: “They’ve offered you more than we were going to ask for.” Holmes told him: “That’s right. Keep schtum.”

Holmes says he learned the art of cultivating contacts from John Bromley, then head of ITV Sport – “the networker par excellence”. Bromley called everyone “commander” to avoid the embarrassment of forgetting people’s names.

With his restaurant and clothes shop investments, Holmes thinks he has timed his exit well. “I’m finishing now because I’ve been at it 50 years. Also I was always quite good at working out where the next bit is coming from. I don’t think I am now. Social media, AI, fake news – I can’t get there. I don’t like social media. I do a podcast [Football Ruined My Life], which I enjoy doing, but there are thousands and thousands of them now.”

Before we walk out into the spring sun, Holmes surprises me with an observation about who are the most formidable adversaries: “The best negotiators are children, who say, ‘Daddy, I need … ’ That word ‘need’. What do you mean by ‘need’? A friend of mine whose son went to university said he had sent him a message – ‘I need a dinner jacket’. My friend thought – ‘What do you mean you need a dinner jacket – at university!’

“You give in. That’s why the power of no is so important in a negotiation. Try ‘no’. That way you find out. Maybe they go away, but you can always go back – and if they get really cross you can say – I was only joking.

“A smile – and humour – are very useful. When I took Luther Blissett to Milan in 1983, the talks took place over a whole weekend.

“I said, look, there’s one problem here. He wants a Lamborghini. Their faces dropped. I said: ‘Only joking.’”

Photography by Antonio Olmos for The Observer