If Joe Lewis’ wild generosity had extended to Spurs, they might have won the title

Reading the pages of Joe Lewis’s indictment one is bound to think that if the Bahamas-based billionaire had been as generous with Tottenham as he had been with certain pilots in his employ, and one particular girlfriend, Spurs would have been Premier League champions by now.

For the people who shared the day-to-day with this 86-year-old recluse from public life there were all sorts of treats. Aboard private yachts and private jets, and in the suites of five-star hotels, he broke the protocols of the financial world over and again. When one of his pilots reportedly told him that he did not have the liquidity to exploit one piece of confidential information, Lewis allegedly loaned him the $500,000 to do it anyway.

One of those pilots, Patrick O’Connor, according to the unsealed indictment from US district court, in the southern district of New York, allegedly told his co-pilot that he knew exactly how to persuade his boss. “I was like a little puppy looking up at him [Lewis],” he wrote to a friend over an encrypted messaging app. “He couldn’t refuse.” O’Connor and fellow pilot Bryan Waugh have pleaded not guilty to charges.

It was a remarkable insight into a man who was the controlling power for years at a club that, under the ownership of Lewis’s investment company Enic, would only spend strictly within its means. Run by Daniel Levy, Lewis’s hard-nosed, tough-dealing protegee, Spurs were often admirably self-sufficient and also parsimonious to the point of self-sabotage. At times it might have been the difference between a league title and a place among the also-rans.

The indictment for misleading the US Securities and Exchange Commission (SEC) is the story of a very rich man – who also sounds like a very lonely man. And despite Lewis having built immense wealth from such humble beginnings, it is hard to read without reflecting on the phrase that there is no fool like an old fool.

Lewis’s grovelling apology to the court in New York comes ahead of sentencing in March when he may face jail. When it was all over the man who once called every shot at one of the most famous clubs in English football left with his face shielded by a crumpled black umbrella.

Lewis tried to hide from photographers after his court appearance on Wednesday – Yuki Iwamura/AP

He risked his whole reputation, and perhaps his liberty, so that his pilots could allegedly profit from confidential trading information. He allegedly paid his 33-year-old girlfriend, Carolyn W Carter, a British Virgin Islands beauty queen, a stipend of $100,000 a year but gave her market-sensitive information which, it is alleged, allowed her to trade for many multiples of that. She also denied wrongdoing.

It would have been a lot simpler to give them the money from his own fortune. But then the super-rich do not think as others. Just ask those Spurs fans who still believe that, for example, but for a couple of judicious signings in January 2016 they might have beaten Leicester City to the Premier League title, instead of finishing third in a two-horse race.

Although this was not just about Spurs’ great Enic lament. It was about how football is run, and the kind of people who own its clubs. Regulation is all but impossible in this bigger picture of billionaires, private equity hawks, nation states and Emirati royalty – whether by the Premier League or the proposed new government regulator. Long before even the Premier League became aware of the SEC indictment, Lewis had transferred his interest in Enic, and by extension Spurs, to a family trust.

In July last year the Premier League said it had guarantees that Lewis was no longer Spurs’ controlling power as it became clear just why he and the club might wish to make that distinction. The Lewis Family Trust now owns what was the patriarch’s 70.12 per cent of Enic, which in turn owns 86.58 per cent of Spurs, and the trust includes Lewis family members.

There will be those who see that arrangement a little differently to the regulatory bodies, but there are none in football – or indeed the government regulator – who can do anything about it. The Premier League is a loose affiliation of millionaires and billionaires that runs, as Richard Masters said to the recent Parliamentary select committee hearing, “on a handshake”.

It requires owners to play by the rules. The Premier League has beefed up its owners and directors’ test as far as it can under British law, without effectively operating a foreign policy programme separate to that of the government. Roman Abramovich only had to sell Chelsea because of government sanctions. But there will be no appetite to make a government regulator get involved in forcing billionaire owners to sell football clubs.

As ever, there is little leverage on the global super-rich owners. They do as they please, as Lewis’ case has shown, until caught – and even then the transferral of their power is on their own terms.

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