Hollinger International requested Deedes’s return to duty as chief executive at the Telegraph – he’d only just vacated the managing director’s chair – when the dispute with Lord Black over unauthorised payments catapulted the group on to front pages around the world. “Conrad’s difficulties became public the night of my retirement dinner,” Deedes recalls. “It wasn’t immediately apparent [how serious the situation was], so I duly retired and went to South Africa, where I always go for a week or two in the winter. Because I’d retired we went for about two-and-a-half months. When I got home I got a message from one of the directors of Hollinger in New York saying would I go back and pick up the pieces and perhaps get involved with the sale of the paper, which they thought was probably going to be necessary. Which I did, with no hesitation at all, and it was great. I was going back to do a specific job and I’d never been intimately involved in a big sale before, so it was a very interesting exercise.”

The turmoil eventually saw the Barclay brothers gain control of the group after an initial arrangement for Black to buy was scuppered in an American court. “There was no shortage of interested parties,” says Deedes. “My job was really to do two things: maximise the sale with the help of [merchant bankers] Lazards and try to be reassuring to the staff, who, understandably in that situation, found it difficult to keep their minds on the job of producing a paper every day. It’s very unhelpful for editors and managements of newspapers to be part of the news, especially as those who write about you are not necessarily well disposed or even neutral when it comes to their opinions of what should happen.”

Deedes completed his dual tasks, maintaining staff morale as best he could and overseeing the sale to the Barclays, who saw off a cluster of other suitors in winning the group’s hand. “I had watched the original deal between the Barclays and Conrad with interest from Cape Town and it certainly looked as if it was all over. I think it meant they were always going to be the favourites to buy – once you’ve got your fingers on something and had it snatched away, you’re probably going to be that much more determined. It turned out that it was an even longer-term vision of theirs than I thought. Aidan [Barclay] told me after the sale that his father and uncle had approached Conrad very shortly after he’d bought the paper in 1986, saying that they would be very interested in buying it. So they’d had their eye on the opportunity for almost 20 years.

“I still believe it was a good sale. It [the paper] ended up with a buyer that is going to look after it for a long time and that’s what the Telegraph [group] wanted. A concern was what would happen if it were bought by a venture capital company, because a venture capital company would in all likelihood repeat the process in five or six years’ time.”

So, although accepting the part-time vice-chairmanship of the company, Deedes sort of retired again. But not for long. Charlie Methven (a former Daily Telegraph journalist), Max Aitken (a great-grandson of Lord Beaverbook), and Ben and Zac Goldsmith (sons of the late business tycoon and gambler, James), sought out the Hon Jeremy, son of journalistic legend Lord Bill Deedes, to head up their new enterprise. The Sportsman is to be a betting newspaper, and betting and newspapers are areas about which Deedes knows a great deal. “I’ve had legs in horses for quite some time,” he says, tanned and relaxed as he sips a late afternoon Coca-Cola. “They’ve never shown a profit and I don’t think there’s been a year when I’ve shown a profit from betting, whether it’s casinos – which I don’t do very much now – or betting on horses. On the other hand, there are all sorts of hobbies where you never expect a return. Nobody gives you money back when you leave the cinema or leave the theatre. All right, you can’t lose a lot at the theatre or cinema, but I would argue that you don’t get the same amount of enjoyment either.”

Deedes’s card-playing career includes being sent by the London Evening Standard to play in the world poker championships in Cannes. He occasionally plays still. “But to be perfectly honest, I’ve never played online. I can’t get my head around the idea of playing a game of poker by yourself, albeit it [really] being against someone you can’t see. I think playing cards, which I very much like doing, is a social event.” The new paper will go head-to-head with the Racing Post, although The Sportsman aims to cover areas of gambling that the Post ignores (though not the lottery. “The point about the lottery is that it is just that, a lottery,” says Deedes dryly). “The Sportsman will contain a massive amount of statistics and a massive amount of information in terms of form and things like that. “It’s a specialist title – you’re either interested in the subject or you’re not, and if you are you might take the Racing Post as well. It will be also online from day one, with the basic product available free, but you will pay for services. We expect some people switch between online and the printed version on the same day and I think that’s the way it’s going to be from here on in, particularly with this sort of publication.”

Raising the necessary capital – around £12 million – is not proving difficult. “I have been very pleasantly surprised how interested potential investors are. At the moment we are quite far advanced with the first investor we contacted and there are one or two people waiting in the wings. The revenue will be fairly evenly-split between advertising and circulation – if anything, circulation will be slightly higher. We haven’t yet said publicly what our cover price will be but it won’t surprise anyone that it will certainly be less than the Racing Post’s.”

If the start-up money looks modest, it is because printing and other areas of the new paper will be contracted out. “The Independent was the first newspaper to understand that you didn’t need to be a printer and it became the first national paper with no printing presses of its own,” says Deedes. “We’ll be like that – we will contract out the printing, distribution and circulation in terms of sales to a third party. If you were to re-invent the whole process, if we were all starting again, the national newspapers would all print and distribute out of the same place and they would have six satellite plants up and down the country, close to the motorways and near to the place of wholesale outlet. You’d achieve scale of economies that would be enormous. As for advertising, we don’t have an enormous canvas for potential advertisers, like a [regular] daily newspaper. Our advertisers are going to be bookmakers and those people with betting platforms who’ve got a product to sell – a narrow but very important field, and they need to be looked after, but we don’t need to have a large number of people going out and canvassing for advertising.”

He delves into his briefcase to dig out the statistics to prove just how the gambling industry has exploded in recent years. “In 2001, UK gambling revenues were £7 billion and by 2004, £40 billion – which gives you some indication of the direction gambling is going. And it is simply not being reflected in any publication, daily, weekly, monthly, whatever. Looking at it from a commercial point of view, bookmakers and others who own these [gambling] platforms, whether they are online casinos or whatever, are frustrated that they can’t get to this new generation of gamblers, who, because a lot of them are not interested in racing, don’t take the Racing Post.”

He brushes aside suggestions of any moral implications of the gambling boom. “Trying to discuss with people who are interested in betting and gambling their morality or otherwise is like having a discussion with people who go to the pub as to whether drinking should be banned. I think that legalising something and having some sort of control over it is much healthier than driving it underground and having it illegal. And that applies to drinking as well – look at what happened in America when they had prohibition. There’s a problem now in America, where half the population is playing online poker, apparently illegally. It’s crazy. I think this Government, who’ve taken a very liberal view of gambling, have decided they would like to retain some control over it, and have everything above ground where you know what’s going on – playing with all cards facing up, if you like.”

His high-profile responsibility in semi-retirement on behalf of The Sportsman will rub along nicely with his background role at the Telegraph group, he thinks. “If things work out as I hope they will, the one may be complementary to the other. Some of the services we are going to contract out we can contract out to the Telegraph, partly because I think they can do these things better than anyone else. But then I would say that wouldn’t I?”

Yes, he would, having been associated with the group since he was born – his father was working there at the time. (The Deedes journalistic dynasty rolls on with Jeremy’s younger son at The Daily Telegraph, while its commercial acumen is strengthened by his brother, who works in advertising at the Daily Mail.) But Jeremy arrived in the journalistic land of his father’s by a circuitous route. With an ambition to become an actor and convinced dad would not fund him through drama school, he applied for and was offered a traineeship at Southern Television. The departure, three weeks before he was due to start, of the programme controller who’d hired him led to Deedes being advised by the executive’s successor to obtain newspaper experience and then re-apply, hopefully to return as an on-screen reporter. He never went back to find out if he could make the switch to TV – “Once you get immersed in newspapers, I think that’s probably it” – and after three years on a local paper in Tunbridge Wells he joined the old Daily Sketch. From there he ping-ponged to and from the Evening Standard (diary editor), Daily Express (deputy editor) and Evening Standard (managing editor) before being hired by Eddy Shah as the launch managing editor of Today.

“Eddy was looking for someone to be, effectively, managing director to help set up and launch Today,” he recalls. “Someone mentioned my name and I saw Eddy, who I think thought that managing editor was some kind of management job, which mine at the Standard wasn’t. I was actually number three on the paper. So I found myself at Today probably wearing false clothes.

“Eddy had made himself a household name through his exploits at Warrington, where he had effectively curbed the power of the trades unions. That in itself created the biggest problem for Today, because we had to deal with everyone outside the normal structure. We couldn’t contract print because the printing works were all unionised and were not going to have anything to do with Eddy Shah. Similarly, all the distributors, both wholesale and retail, were unionised and were not going to touch Today. So we had to invent every single part of the chain, from putting the words on to a computer right through to delivering the paper through the letterbox. The normal supply chain just wasn’t available, which is why, I guess, the paper was not as successful as it should have been. Pre-launch we actually had more orders for home-delivered copies of Today than we knew we could print and our own distribution system couldn’t have coped with them anyway.”

When Max Hastings approached Deedes to join The Daily Telegraph management team he initially declined, but changed his mind when told by Shah that Today was to be sold. He insists The Daily Telegraph’s overall performance during his time there was good, despite the paper’s problems when Rupert Murdoch’s cost-cutting exercise at The Times drove its back to the wall. “As a free marketer, I have nothing against that,” he says, “but what Murdoch did to the newspaper industry [by slashing the price of The Times to 20p, and 10p on Mondays] was to devalue the worth of a newspaper in the eyes of readers. People began to think that 20p was what a serious newspaper was worth and should cost. We haven’t yet got back to re-establishing in people’s minds what value a newspaper really has. I’ve always used the British Rail cup of tea as being quite a good yardstick. What’s the cheapest cup of tea you can buy in a railway station? If any paper I’m working for costs the same or less, I think that’s pretty good value for money.”

During the period that Conrad Black was in control, the paper continued to produce good profits, Deedes points out. “As a whollyowned subsidiary, our job was to maximise profits and effectively ship those back to America. We always saw a great deal of Conrad – he was in the office most days, he used to come to my management meetings and would stay on and have lunch with senior staff – and jolly good lunches they were too. I think that Conrad, in many ways, was a model proprietor. He knew what he wanted and he largely left the editorial staff and the management to get on with it.

“But when he started to research and write his biography of Roosevelt, we saw less and less of him and he seemed to be in England much less. I don’t say he became less interested, but certainly he was much less hands-on. And in newspapers you have to be thinking all the time, what are we going to be doing tomorrow, what are we going to be doing next week, how do we stay ahead of the game? In the early years he was never frightened of investing – if you put a good case he’d listen and if he agreed he’d provide the money. One of the consequences of his being there less and taking his eye off the ball is that it was much harder to get his attention and therefore things took longer to get through. The re-planting, which is something we should have been acting upon much earlier, was a very, very long, drawn-out process before we came back to square one, which was buying new presses. We were then behind the game where we could have been ahead of the game. In the first part of Conrad’s life as proprietor we would have been.”

Although Lord Black has re-emerged in London, if less flamboyantly so than during his previous residency, Deedes hasn’t seen him. [But] “I would like to think we were friends. We got on well and I greatly enjoyed his company. And I think it’s incredibly sad from the paper’s point of view, and from a lot of individual people’s points of view, that things happened the way they did. But, as they say, life goes on, and this great, wonderful piece of well-oiled machinery with all this flak flying all around it just rolls on and continues to produce what I think is a very good newspaper. The escalator is not allowed to stop – you can’t put up a sign saying ‘Out of order’. It’s a great credit to the staff – their resilience demonstrates that journalists aren’t a bunch of drunken layabouts, as they’re sometimes made out to be. That’s when they can really be seen at their best, when things are going wrong.”

He remains optimistic about the future of newspapers and advocates investment in the web and availability in whichever form the public demands. “But it doesn’t mean that because it [any alternative distribution process] is technologically clever, it is more acceptable. If you reverse the process, if there were no newspapers but only all this information on line, and you had to switch on a computer every morning to find out what was happening, then the newspaper would have to be invented. Someone would eventually have the idea of getting up in the middle of the night and writing a précis of what was inside that box, putting in on a piece of paper and shoving it through the letterbox so that you could read it at the breakfast table without having the bother of turning on that machine.”

And the future of printed news, he thinks, is largely tabloid. When at the Telegraph, he was “tremendously excited” about the prospect of offering a tabloid version of the daily paper, at the same price and with the same content, alongside the broadsheet. The move solely to tabloid or “compact” production by The Independent and The Times disabused him of the idea: “What they very successfully did on behalf of the Telegraph was to demonstrate that no matter how nice an idea that was, it was logistically an impossibility. I’ve been forever grateful that they did that on our behalf and that we didn’t have to go to the expense of finding it out. I believe right now the Telegraph is right to stay where it is. It is going to be very interesting to see what happens when the Berliner-size Guardian comes out. I personally think it will really suit The Guardian, even though it’s a shape alien to British readers. Maybe that’s the way forward for the Telegraph, maintaining the essence of being a serious newspaper with a convenience in size for people who don’t read their papers on the kitchen table.”

Deedes is far too loyal a Telegraph man to be drawn into any controversy over the supposed one-time precarious position of daily paper editor Martin Newland and the sacking of Sunday editor Dominic Lawson. Originally rumour suggested that the Barclays would remove Newland in favour of Lawson. “There was speculation inside and outside the Telegraph building and it must have been difficult for both of them, but particularly difficult for Martin, of whom I was a huge supporter,” says Deedes, carefully. “I was involved as managing director with Conrad and [chief executive] Dan Colson’s deliberations as to who should replace Charles Moore and make no secret of the fact that Martin was the number one choice. He’s the exactly the right kind of person to edit the Telegraph, for today.

“The point about editors is that it’s timing – whether they are right at that particular time. Max [Hastings] was just absolutely the right person to be editor of The Daily Telegraph in 1986 – it needed an enormous spring clean, and while I’m not saying it didn’t need changes in 2004, they were not of the same order. Martin is exactly the right person for this moment.” Lawson’s departure did not surprise him, he says. “Nothing surprises you in journalism” – and “I think he did a lot of good things. [But] He had done it for almost 10 years – it goes back to editors being right for the moment. Time moves on and sometimes a fresh pair of eyes is what’s needed. I’m jolly glad Sarah [Sands] has got an editorship because she was probably disappointed that she didn’t get the daily. She’s an outstanding journalist. She’s got antenna for what’s happening at any particular time and how to reflect that in the newspaper, which, in recent years, only David English has had.”

Not the Daily Mail’s current editor, Paul Dacre, I query? “It’s a different sort of antenna – Paul’s certainly more of what I would call a nostalgist, rather than looking forward. David was always interested in what was coming up, what was going to change our lives tomorrow. His Mail always told you before anybody else things that were going to happen in this country – in cinema, inventions, whatever. Sarah has got those sort of instincts, for what is going to happen tomorrow, what’s going to be interesting and what people are going to be talking about next week rather than this.”

Deedes is equally circumspect when recalling the much-publicised incident when, in front of a Telegraph team discussing shared printing company, West Ferry, Express group proprietor Richard Desmond launched a tirade of abuse against German publishing house Axel Springer, then bidding for the Telegraph publications. At the time, after leading his team’s walkout from the meeting, Deedes described Desmond’s attack and goose-stepping around a boardroom as “the most grotesque outburst of a mix of slander and racism I have ever been subjected to. If it had been a public place he would have been arrested”. Now he reflects: “At the time it happened it did slightly surprise me. It was an embarrassment. We were in negotiation with Axel Springer and I have to say a more professional group of people I’ve never come across. So, although they weren’t there, it [Desmond’s outburst] was sort of being rude to people who had been very polite to us. That’s what at first slightly surprised me and secondly made me cross.”

But does he harbour rancour? “Good God, I don’t bear grudges – life is far too short for that – and anyway I have had some extremely agreeable moments with Richard Desmond. I’ve had tea with him. He didn’t ever say sorry, but here’s just a small thing… in the middle of it all, my mother died, and in spite of the fact we were having this spat, he wrote me the most incredibly nice and kind card, saying how sorry he was. Anybody who can do that isn’t all bad. The Express has had some far worse owners than Richard Desmond.”

With which Mr Deedes, a gentleman from the top of his head to his renowned mustard-coloured socks, departs to resume his semiretirement business of making himself available to the Telegraph for polite advice when required while also putting The Sportsman on the road. His belief in his new venture is reinforced by the fact that, along with the other founders, he has personally invested in it. With his experience, contacts and sang-froid on tap, it doesn’t look like too wild a gamble.