Peter Middleton: Athlete and novice monk who became a spy and diplomat before turning round Thomas Cook and Lloyd’s of London

When he asked to see Lloyd’s accounts he was told they went back only three years

Middleton leaves his first press conference at Lloyd’s in 1992 (Martyn Hayhow)

Not many CEOs could claim that before going into business, they had seriously considered a career as a monk. Yet in Peter Middleton’s case, this was just the tip of the iceberg. A firm believer that no system of risk management, however sophisticated, could completely take into account the infinite variety of human character, he was himself a proof of that general rule.

Middleton rose to prominence at the helm of the insurance market Lloyd’s of London in the early 1990s, towards the end of its crisis years, but before then he had been a diplomat and spy, studied philosophy at the Sorbonne, and come within a whisker of representing his country at the 1968 Olympics. In that last endeavour, he claimed, he had only been denied a place by a sore Achilles tendon.

Born into a working-class Catholic family in Yorkshire, from an early age Peter James Middleton had a sense of belonging to a different destiny. In his teens he entered a monastery in Devon, intent on a life of cloistered contemplation. “I was very much attracted by a way of life in which the material possessions side of things was not a dimension,” he recalled. After several years, chafing at the requirement for absolute obedience, he quit and moved to Paris to study philosophy. A year later he was back in England, working as a lorry driver to make ends meet. It was then that he conceived an ambition to write “the definitive history of the 20th century” - but to achieve this, he realised, he needed to know something about economics and social science. To which end he enrolled at Hull University.

There, as it turned out, he devoted more time to competitive running than his books, specialising in the 400 metres and 800 metres events. When injury put an end to his athletic prospects, he entered the Foreign Office, and was posted to Paris with a secret brief from MI6 to gather intelligence about communists. His subsequent diplomatic career took him to Jakarta, Tanzania, then back for a four-year stint in Paris.

In 1985, Middleton’s unusual personality – a hard-drinking, plain-speaking Yorkshireman with a penchant for philosophical speculation – caught the attention of headhunters at Midland Bank International, and he embarked on a new chapter. The bank owned the ailing travel agency, Thomas Cook, and Middleton was given the task of making it saleable.

On his first day in the canteen he was dismayed to discover there were three eating areas for staff, depending on seniority. He plonked down his tray of pie and chips with some junior workers and introduced himself. Noting his northern accent and casual sweater, they refused to believe he was the new boss, so he took them to his office for a post-prandial coffee. Against the odds, Middleton turned the company around, and a few years later sold it for a healthy profit.

This extraordinary success story led directly to the job at Lloyd’s in 1992 – his toughest remit. When Middleton asked to see the accounts he was told they only had three years’ worth. This sclerotic tradition went back to the 18th century, when it had taken three years for an insured ship to return from a round-the-world trip.

There was also the fact that most of the underwriters were, in Middleton’s endearing phrase, “dumbos”. He got rid of the weakest ones and set up a new company, Equitas, to handle the bad debt. Having incurred massive losses, Lloyd’s began to make a profit. Yet Middleton still came in for criticism when he left before his contract was up, lured, it was said, by the vastly greater salary he would receive as CEO of the European branch of Salomon Brothers.

There had been controversy, too, about his private life, with reports in the press of extramarital affairs, including one with the novelist Samantha Phillips, who loosely fictionalised Middleton in Blonde Ambition (1996). “His grip was light and strong,” she wrote, “his voice low down the scale, a soft voice with a hard edge, iron under velvet.” In the year this breathless roman à clef appeared Middleton divorced his first wife, Yvonne, and married Anita, a prison hospital nurse 25 years his junior.

At Salomon he pursued his hands-on, humanist approach to risk management, emphasising that a CEO should really get to know his traders. “You walk the floor,” he insisted time and again. “And you look to see who’s looking pale. You look to see who’s averting their eyes from you, or who’s looking happy.” For all his people skills, however, not everyone appreciated the boss peering over their shoulder, and he was removed from the role after less than three years. Thereafter he kept busy with a string of lesser directorships.

To let off steam, Middleton listened to rock music, followed the fortunes of Middlesbrough FC, and, when the stress was getting to him, leapt aboard his 800cc Suzuki motorcycle. “For relaxation,” he once declared, “I’ve found nothing to beat getting on the bike and for going for a bit of a ride up the M3. The entries on my driving licence prove it.”

Peter James Middleton, businessman: born Withernsea, Yorkshire 10 February 1940; married 1968 Yvonne Summerson (divorced 1996; two sons, one daughter), 1996 Anita Mehra (two sons, one daughter); died 15 March 2014.