He and his Spanish partner thought they had pounds 2m in sponsorship to support five concerts and, on that basis, agreed to pay the singer pounds 4.5m. But the sponsors changed their minds, and all the two promoters had to wave in the courts was a fax. 'We learned about Spanish law the hard way,' he says. 'Faxes aren't binding in Spain. So we lost pounds 2m.'
Deeny finds it easy to make money, and almost as easy to lose it. A 49-year-old Northern Irishman with an engaging smile and a serious stammer, he is a born entrepreneur. His skills at negotiating and organising were honed as a music promoter, but for the past two years he has used them - at least for 50 out of the 80 hours he works each week - to co-ordinate the biggest compensation campaign mounted by Lloyd's names.
On Tuesday, he was rewarded with a High Court decision that could mean that the 3,096 Gooda Walker names share pounds 504m. Not only was this by far the largest award made by an English court, it paved the way for other settlements that could finally bring the Lloyd's saga to an end.
Deeny has been given much of the credit for the success. Tom Benyon, vice-chairman of the ginger group, says he had the characteristics needed to force the complex case through to its conclusion. 'He's as tough as an old army boot, as well as being very ambitious and competent, with a high attention to detail,' he says. 'He also tolerates fools for about three nanoseconds.'
A sign of the man's toughness, Benyon says, is his willingness to talk to hundreds of people in meetings, and to go on television, with a serious speech impediment. 'Many people thought that would be a handicap at first,' he says. 'But it has clearly toughened him immeasurably.'
You forget about the stammer after a while, anyway, because Deeny keeps up a parade of other minor eccentricities as he talks - pacing around the room, sitting down suddenly, stopping dead in the middle of a sentence, pacing around the room again . . . He is an exhausting man to watch.
Last week's triumph followed a campaign in which the Gooda Walker names had tried to prove that they were victims of sharp practice, not bad luck. The syndicates they joined made their money by reinsuring other syndicates against catastrophic losses. It was by its nature a risky business but, the group claimed, Gooda Walker had consistently overstated profits by using legal but misleading accounting devices. When a series of disasters, including the 1988 Piper Alpha explosion, triggered vast losses, the syndicates were overwhelmed, and the names were asked to bail them out. As a result, many faced bankruptcy.
Deeny has been a member of Gooda Walker syndicate 290 since 1985, and he joined the action group committee in 1991. Two years later, a palace coup overthrew the autocratic Alfred Dol Steinberg and installed Deeny in his place. 'We needed someone who could see things more consistently and in the round,' a leading name says.
Deeny was born in Lurgan, near Belfast. His father was a doctor who liked to claim lineage from the (legendary) hero Diarmaid Ua Duibhne. The Deenys were an old Catholic family who had lost their lands to the English in the seventeenth century but had long shed their bitterness. 'My father was unusual in having a significant number of Protestant patients,' Deeny says.
He was sent away early to Clongowes, an old Jesuit school in the Republic which James Joyce had also attended, before going to Magdalen College, Oxford, to read history. He spent three years in the late Sixties qualifing as an accountant in the City, although he never intended to make it his career. Moving to Dublin, he soon found himself turning a hobby - live music - into a career. His forte, he discovered, was in organising and negotiating, and he soon became one of the most successful promoters around. 'I was doing something I enjoyed, but also something where it was possible to make quite a lot of money,' he says. He has promoted concerts for Bruce Springsteen, U2 and Pavarotti, among many others.
After moving from Dublin to London to New York, he settled as a tax exile in the Cap d'Antibes in the early 1980s. 'The advantage of music is you do all your work on the phone and fax - it does not matter where you are,' he says. 'But the problem with the Riviera is that you spend most of the tax you save in the restaurants there.' He made his bread and butter arranging concerts in France, where his best contacts still are.
He joined Lloyd's in 1985 on the advice of his brother, a barrister in Northern Ireland. 'I thought it was a very traditional old-fashioned English investment,' he says wryly. 'In the music business, one's income can fluctuate alarmingly - I thought it would be nice to have an additional stream.'
He was never, however, a typical name who expected a pleasant combination of regular cheques and social prestige. He looked long and hard before putting his faith in Derek Walker's syndicate 290. 'The art of making money as a Lloyd's name is to be in the right syndicate: it doesn't cost any more to be in a good one than a bad one.' The very best syndicates were difficult to get into, but 290 appealed, because it apparently had a good profits record and vacancies.
But in 1989, the syndicate turned sour. And after the Prince fiasco two years later, he had to trade down from a manor house in Oxfordshire to a more modest affair outside Salisbury. He remained philosophical, though, and looked forward to a little peace. 'I thought I had organised my life to live in the English countryside and pop over to Europe for concerts occasionally,' he says.
The peace did not last: he could not resist joining the Lloyd's action group in 1991. 'Partly my own losses were large enough to be painful,' he says. 'But the real reason was that the more I found out about it, the more angry I got as it emerged that we weren't victims of fate, but of negligence.'
In 1992, he became a member of the litigation sub-committee and the next year, at Mr Benyon's instigation, became chairman. 'I recognised he had a steel-like quality,' Mr Benyon says.
Unlike for many Lloyd's activists, Deeny's marriage has survived the strain. His wife, Maggie, is a child psychologist, and they have three children of 13, 11 and nine. He manages to spend the weekends with them.
Deeny's wealth is at a low ebb, and there is plenty of work still to do with the Action Group. But eventually he will be allowed to get back to his rural idyll, and to his natural activity - making money. There is time to make and lose a fortune or two before he finally hangs up his fax.
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