As a Pink Floyd-loving public schoolboy in the mid-1970s, Adrian Newey found a clever way around his headmaster’s ban on platform-soled shoes. The relevant rule stipulated that if you could pass a penny on its end between the ground and the sole of the shoe, it was illegal. Newey reacted by glueing a strip of aluminium between the heel and the sole, thus reducing the gap while maintaining the desired height of the shoes. “No prizes for spotting the connection between that and what I do now,” the technical chief of the Red Bull grand prix team writes in his autobiography.

What Newey does now is find ways around the most complex set of rules ever devised to control a sport: the Formula One technical regulations. Each time they are rewritten Newey sits down to decide how he can make them work to his advantage, ignoring what the rules were intended to do and concentrating instead on what their wording will allow him to get away with.

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It is an endless process. Once Newey has spotted the loophole that allows him to produce a faster car than anyone else’s the rule-makers rewrite the regulations in order to foil him and he has to start all over again. All F1 designers are in this business but for the past 20-odd years, while winning 154 grands prix and 10 constructors’ championships with Williams, McLaren and Red Bull, Newey has been smarter and more creative in response to the challenge than any of his rivals.

The attitude that eventually got him expelled from Repton produced the cars that took Nigel Mansell, Alain Prost, Damon Hill, Jacques Villeneuve, Mika Hakkinen and Sebastian Vettel to the drivers’ world championship. Newey is a visionary who approaches the job of designing these phenomenally complex machines standing at an old-fashioned drawing board, making freehand sketches with a propelling pencil, with two assistants on hand to translate the results into digital form. And the job is never far away. On a holiday beach in the Maldives a sudden brainwave has him reaching for paper and pencil.

His book, titled How to Build a Car, is designed to look like a workshop manual. It contains diagrams of aerodynamic flow, which is his speciality. But how many workshop manuals include advice on the arrangements a divorced father might make for his children’s visits, or a description of the physical fights that took place when the author’s parents had been drinking?

Facebook Twitter Pinterest Adrian Newey, second right, and the Red Bull chief, Christian Horner, right, talk with drivers Sebastian Vettel and Daniel Ricciardo, left, at the launch of the team’s 2014 F1 car in Jerez. Photograph: Andrew Hone/Getty Images

Newey’s honesty is balanced by an anarchic sense of fun – well hidden in post-race interviews – which leads him to give witty and acerbic glimpses of the character of the people and organisations with whom he has dealt over the decades. In his first job in F1, with the short-lived Fittipaldi team, he encountered an organisation that “ran on a diet of cigarettes, coffee and beige polyester” (this was the early 1980s). He recalls the big-name French aerodynamicist Max Sardou, whose designs he was assigned to improve, as always wearing a trenchcoat – “even in the middle of summer” – and driving his road car with the wing mirrors turned flat in order to reduce the wind resistance.

He remembers Mansell as “an attack dog in the car. When he drove it, you knew it was being bullied into submission. You knew he was giving his best.” Prost, on the other hand, was one of those drivers who would “build up slowly, particularly in testing, never really stretching themselves or the car, so by the end of the day you’d be fretting, thinking: ‘Oh God, this thing’s slow,’ when it was just that Alain wasn’t really extending himself.” There’s not much doubt which approach Newey prefers.

In the light of recent events his verdict on Lewis Hamilton, with whom he worked at McLaren, is interesting. “He’s a tremendously friendly guy,” he writes. “True, he’s gone a bit showbiz in recent years but he’s one of the few drivers who will stop and chat, give people the time of day.”

Many of those who pick up this book will turn straight to the passages dealing with the early weeks of the 1994 season. They will be looking for fresh information or insights from the man who designed the difficult Williams FW16 that Ayrton Senna drove during his three races with the team. Following the Brazilian’s fatal accident at Imola, Newey was jointly charged with manslaughter before being exonerated by an Italian court.

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He has interesting things to say about the circumstances surrounding that melancholy weekend, confirming the impression that Senna had his suspicions about the legality of Michael Schumacher’s Benetton. The opposition, he says, were “not playing with a straight bat”. But it was Newey who, in the runup to the tragedy, devised a welded modification to the car’s steering column in answer to Senna’s request for something to stop his knuckles rubbing painfully on the inside of the chassis. A popular theory suggested the Brazilian lost control when the shaft broke at the improvised weld, or that it fractured after the car had started to break away, leaving the driver helpless.

Newey agonises over the possibility but eventually discounts it. “What I feel the most guilt about,” he writes, “is the fact that I screwed up the aerodynamics of the car.” He had produced a machine whose inherent instability contributed to the crash. By the time they got to Imola he had figured out what the problem was but solving it required more work, first in the wind tunnel and then in manufacturing new parts. “Time denied us all that chance,” he concludes.

This necessarily sombre note falls midway through the tale of a boy who left school with some pretty damning judgments ringing in his ears – “disinterested, slapdash and rather depressing”, “behaviour extremely silly” – but eventually thought, rather than fought, his way to the very top of his sport.

Newey is the most successful F1 designer in history but it is three years since one of his cars won a world championship. What we can be sure of is he will have spent the winter examining the regulations all over again, seeking the vital loophole to which he can apply his gift for “disruptive technology” – his term for getting around the rules.

He makes no effort to disguise the price paid for that kind of success. “Marigold [one of his former wives] said I was the most selfish person she knew,” he reports, without flinching. This is, after all, a man who estimates he has spent a quarter of his entire life in a wind tunnel and does not appear to regret it.

• Richard Williams’s column will appear in Tuesday’s Guardian from next week