If Allardyce had got England to the World Cup finals in Russia, he would in all likelihood have been the best rewarded manager there. Why exactly was he looking to leverage that position so soon? Why wasn't the challenge, the honour and prestige, not to mention the 3 million ($5.34m) salary, sufficient?
What is so mystifying is that it has all been so unnecessary. Allardyce could not have appeared happier with the way his life had turned out. The FA are loyal employers, some might even say easily pleased. What was he looking for around that table at London's May Fair Hotel? What more could he possibly want?
No sooner had Allardyce got his new motivational messages up at St George's Park - "the journey starts here", one read - than he was looking to make his own journey, out to the Far East as a keynote speaker and glad-hander. A loose cannon for hire. Standing at the bar, after having a few social drinks, as he put it.
And what would the conversation be about? Well, what would you have asked, given the chance to talk football with the England manager over a beer? Wayne Rooney, Harry Kane, Joe Hart, Marcus Rashford. Allardyce was as good as serving up the sanctity of the dressing-room for a price. With his new friends - who turned out to be reporters from the Daily Telegraph, not the meal ticket he imagined - he was disparaging about Roy Hodgson and Gary Neville. He could hardly then claim to his FA employers that he would have been any more discreet at last orders with that evidence on file.
From the start, Allardyce played up to the idea he was the proudest of proud England managers. It was his dream job. His life's work. The pinnacle of pinnacles.
For, even had he survived, the revelation that England's manager was very much for hire would have left him irrevocably damaged. The purity of the appointment, its simple innocence, was gone.
Allardyce was English football's boy done good. His appointment was a triumph for the little man, for the idea that the Bolton manager could be as sharp as Jose Mourinho, given the chance. Allardyce wasn't an imported mercenary, here for the money like Sven Goran Eriksson or Fabio Capello. He hadn't been around the block with Switzerland and Finland like Hodgson.
Allardyce, we thought, was different. England was his calling. It turns out he loved something even more.
During the fateful meetings, Allardyce said his friend Sir Alex Ferguson received "four hundred, five hundred grand a pop" for speaking engagements. Robbie Williams, he said, got "1.6million for a wedding - just singing". This is where he saw himself: as Ferguson, the most successful British manager in history, or Robbie Williams, seven No1 albums.
Allardyce's highest Premier League finish was sixth and he hadn't even taken charge of an England game at the time. "Keynote speaking, that's what I'd be doing," he told his audience. "I'm a keynote speaker." The delusions were almost piteous.
England managers have always had the chance to exploit marketable opportunities. Hodgson had an agent for commercial work, too, but there were strict instructions around conflicts of interest. Even Eriksson waited before putting his name to a compilation of classical music. His three-CD collection came out in April 2002, after the 5-1 win over Germany and having secured England's place at the World Cup.
Allardyce didn't even wait for a debut fixture in Slovakia before seeking to mine lucrative spinoffs. As he did, his relationship with the job, and with the country, changed.
At a St George's Park briefing on August 22, a week before announcing his first England squad, journalists were surprised by a couple of verbal slips from the new manager. He referred to Marcus Rashford as "Rushford" - and it wasn't just his Black Country accent because he pronounced it correctly the following week - and called Zlatan Ibrahimovic "Zoltan", like the Flash Gordon villain.
But nobody reported it because this was early, the honeymoon period. He might be nervous. He might be one of those chaps that is absent-minded with names. Sir Bobby Robson was, too, and it worked out for him in the end.
There was an element, too, of cutting the local lad some slack. It took Eriksson some while to live down not knowing the identity of Sunderland's left-back. So Allardyce was perceived, and treated, differently.
Except he wasn't different. The pinnacle, the dream - it wasn't enough for him. He wanted more. He wanted to be Robbie Williams. He wanted to be a keynote speaker. And now he can be. Here he is, ladies and gentlemen - Sam Allardyce.
Tonight's subject: Regret.
