A friend of mine was leafing through a recent copy of the American magazine Vanity Fair, which carried an interview with Conrad Black, whose trial in Chicago starts today. He tells me that Conrad is quoted as saying that only three friends in London have remained loyal and that he names me as one of them.

It is a compliment I greatly appreciate. One should stand by one’s friends when they are in trouble, though none of us has a 100 per cent record in that respect. I have disliked the unseemly glee with which some of those who drank Conrad’s champagne, always offered in generous quantities, have greeted his misfortunes.

I cannot claim to have done anything much to help Conrad, except to let him know that I am sorry he is in trouble and still regard him as a friend. In fact, our friendship is more a friendly acquaintance. I first met Conrad about 30 years ago. I had been invited by Ken Thomson, who was then the proprietor of The Times, to give an after-dinner talk in Toronto.

He had invited the young Conrad, who would then have been in his early thirties, as a guest. Conrad was in those days rather a quiet young man, with the good manners of the serious Canadian. When we next met, he was the proprietor of the Telegraph Group in London.

After that we met at his annual summer party in Kensington, a party that has been used against him. In fact, newspapers and the BBC normally do give parties, partly for promotional reasons, partly to broaden their contacts and partly for staff morale.

One can compare the cost of these parties with those of a wedding reception. So far as I know they are usually treated as legitimate business expenses. Conrad’s parties, which were given at his home, mixed politicians with journalists, mainly drawn from his own newspapers. At the time I always assumed that the parties were a business expense for the Telegraph group; they were attended by political figures up to the stature of Margaret Thatcher.

Apart from these parties, I remember going to a dinner for Henry Kissinger, which was quite sumptuous. Barbara Amiel is a meticulous hostess. Kissinger made an excellent speech. I once gave Conrad lunch at the Garrick Club to introduce him to an American friend who shared his views of Anglo-American relations, which were similar to Andrew Roberts’s belief in the English-speaking alliance. Our last substantial conversation was at a summer party, given by Tom Stoppard, at the time of the publication of Conrad’s Life of Roosevelt, a biography I admire.

I cannot usefully comment on the charges that are being tried in Chicago. No one has yet heard the evidence. However, it is not obvious to me that the disputed “non-complete” payments necessarily belonged to the Hollinger shareholders rather than to Conrad Black. In practical terms, Conrad was the competitive entrepreneur, and Hollinger without him was a mere holding company. No doubt the point will be argued in court.

I suspect that Conrad knew that he had recurrent urges to take risks that he ought not to have taken. A few years after he had bought the Telegraph he gave an interview in which he said that he had had to “stake the farm” on the Telegraph deal, but was now back in a stable position. He said that he would never stake the farm again.

Obviously, he did not stick to that resolution. In financial terms, he had no need to take the risks that he did, including the avoidable error of trying to establish a national paper for Canada in competition with the strongly entrenched Toronto Globe and Mail.

Nevertheless, risk-taking entrepreneurs are essential to the development of the economy; they have been particularly important in media businesses. The man who created the modern British press was Lord Northcliffe, the founder of the Daily Mail. Northcliffe had the same creative energy as the leading proprietors who have followed him. Even though he has now lost all his newspapers, Conrad had the same sort of risk-taking creative temperament.

I am flattered to be counted among the few who have not turned their backs on him, but the larger group that I find are still quite sympathetic are among the Telegraph journalists. Of course, no journalist wants his proprietor to get into financial trouble; there will always be a knock-on effect on the newspaper and on journalists’ jobs. Yet many Telegraph journalists remain impressed by Conrad’s choice of editors of The Daily Telegraph, including Max Hastings and Charles Moore, and of The Spectator. They saw that his habit of writing letters of complaint to his own newspapers was a recognition of their right to disagree with him. They liked his belief in freedom of argument. And they were impressed by the scale of his personality.

Conrad admires the dominating figures of history. He is fascinated by the great American presidents, Abraham Lincoln and Franklin Roosevelt. He is fascinated by Napoleon. These are rather dangerous role models, particularly Napoleon. The extravagance of Conrad’s imagination made him creative, but he did not have the careful eye for the cash flow that is the rule for serious businessmen.

There is, of course, one figure who leaps out at one as the true role model for Conrad; not Napoleon, not Beaverbrook, but the Great Gatsby. They have the same energy, the same liking for hospitality, the same big romantic illusions, the same virtues and some of the same flaws. I am not sure this is a comparison for which Conrad would thank me. But the Great Gatsby, though the story ends in tragedy, was the hero of the greatest novel ever written by an American author.

Times Recommends

• Tear down this wall! And save the planet
• Double click if you want the bin emptied
• Have you got permission to read this?