David Dein: ‘We had something special at Arsenal. When it fell away, that really hurt’

The pen sits in his jacket. It goes everywhere he does. At night, while he sleeps, it rests on the bedside table alongside him. David Dein has been in business for more than half a century, and one of his earliest lessons was that it helps if you have a story to tell. And so now he holds it up to the camera: the Mont Blanc pen with which he signed Dennis Bergkamp, Thierry Henry, Sol Campbell and many more.

Not that Dein needs a memento to remind him of the good times. At the age of 79, the memory is as sharp as ever: an Arsenal fan who became their owner, their saviour and later their martyr. The highlights of his career are also some of Arsenal’s: the league title in 1989, the Invincibles of 2004, the signing of a little-known French coach called Arsène Wenger.

These are the memories that gild Dein’s new book, Calling the Shots. But there are painful stories in there, too: in 1984, his sugar -exporting business was defrauded out of £15m by a criminal conman, an ordeal he has never shared before. And the most painful recollection of all has a precise date and time.

“Eighteenth of April 2007, at 5pm,” he says. That was the moment when Peter Hill-Wood, the Arsenal chairman, walked into his office to give him his marching orders. For months, Dein had been engaged in internal boardroom wrangles over the funding of the new stadium, and his plan to attract outside investment to fill the club’s financial black hole. Finally, Dein was ordered to pack his belongings and leave the building immediately. He took out his phone to inform his family. It had already been cut off by the company.

“I’ve never spoken to anybody for 15 years on how I left Arsenal,” he says now. “I’m not a person that likes discussing negatives. But I’ve nothing to be ashamed of. I want the club to do well, irrespective of how I left and how Arsène left, which was equally as painful. We’re both bruised over it. Because that was unfinished business. We had something really special. And when it fell away, that really hurt.”

The warmest passages of the book are reserved for the Invincibles side, a team that Dein treasured like his own family. “It was a moment in time,” he says. “I remember after each game, I used to go down to the dressing room and shake the boys’ hands. And Sol Campbell’s words always ring loud and clear. ‘Mr Dein, we’ve just got to keep it going.’ And they did. We assembled a group of players, and they all played the same music together.”

And so, after his sacking, Dein watched Arsenal from afar as his old friend Wenger struggled to keep this decaying institution afloat. “They made mistakes, no doubt,” he says of the current board. “Bad mistakes over the years in the transfer market, and how they’ve run the club. But the good news is that it’s 15 years since I left, and they now appear to be on an upward trajectory. The ship has been stabilised.”

Dein still goes to as many home games as he can. But these days his time is very much divided. He is an ambassador for the Premier League and the FA, worked on England’s doomed 2018 World Cup bid, has served on numerous Fifa and Uefa committees. But the project that animates him most is the Twinning Project, a mentoring scheme in which football clubs run courses in local prisons, allowing inmates to learn vital skills and qualifications. He has visited all 113 prisons in England and Wales, and seen first-hand the dysfunction of the system.

“I can talk to you for a long time about this,” he says. “They’ve been underfunded, a lot of them are short-staffed these days. Prisoners are put behind bars for too long. You wouldn’t put a dog in a cage for 20 hours a day, but some offenders are. The chance of rehabilitation is minimal. And it’s costing £48,000 a year to keep somebody in prison. They’re humans, they’ve lost their liberty, they’ve lost their job. So give them a chance to be better people.”

The conversation turns to wider issues within football, and it is here that Dein’s views are more contentious. He is sceptical, for example, about the idea – recommended in the recent government white paper – of fans on club boards. “I don’t know any club where one of their directors isn’t a fan,” he says. “There are owners like myself, where my money followed my heart, and the newer generation of owners who invest in a football club and then become supporters in a club. With the Arsenal supporters’ club, very often I shared their concerns, but they had to understand ours. They would say: ‘Spend money, buy the best players.’ Easier said than done, right?”

Competing with the state-powered financial giants of the game became a bitter theme of Wenger’s later years, and there is an irony here. No one in Dein’s time at Arsenal worked harder to secure billionaire investment than Dein himself. “We didn’t have a muscular financial investor,” he says. “And I could see the way it was going with Manchester United, then Manchester City, and latterly with Newcastle. We needed a master investor, a billionaire. I didn’t want Arsène to get left behind.”

Is that a good thing for football, though? “It’s where we are,” he retorts. “It’s a competitive industry. And I’m afraid, particularly at the top level, money has a lot to do with it. I think the owners are dedicated. I think their motives are correct. We can talk about the European Super League, which was a disaster. But the majority of them are expecting a return on their money.”

And this is perhaps the paradox of Dein: a man whose footballing journey is shrouded in romance, and yet one of the hardest and shrewdest realists of them all. A walking box of memories who accepts that his club and his sport have changed irrevocably. “It’s inevitable, Jonathan,” he sighs finally. “You can’t stop the tide coming in.” And whether in business, or football, or life, it feels like the truest and most painful lesson of all.