Comolli has revealed that he was offered the chance to sign the West Ham United star - then at Saint-Etienne - and says he would have brought the then-20-year-old to White Hart Lane for just £7.6 million within two years.
However, the Frenchman was dismissed from his role in Tottenham's hierarchy in 2008, having spent three years recruiting players for the North Londoners, and the Payet transfer never materialised.
The France playmaker has enjoyed a ridiculous last nine months or so, scoring 12 times and setting up 14 goals for West Ham in an excellent first season in England following a £10.7 million switch from Marseille last summer, while he has also lit up Euro 2016 with a number of superb performances for host nation les Bleus.
But could he have ended up at Tottenham had history been a little different?
“When I was at Spurs the Saint-Etienne president telephoned me one day and said, ‘Listen, we’re on the point of signing this player, Dimitri Payet, from Nantes for €4million’,” said Comolli to The Standard.
“That was an enormous amount of money for Saint-Etienne. He said, ‘I wondered if you’d be interested in buying him for Tottenham in two years’ time for €10million’.
“I said ‘yes’. I didn’t think the player was ready at that point to play for Tottenham but I thought that after two years at Saint-Etienne he would be ready — so I said it was something that I’d be interested in. As I left Tottenham and ended up at Saint-Etienne it never materialised. But back then Payet was already a player that I liked a lot, having seen him when he was young at Nantes.”
Of course, Payet back then was not the same player he is now, otherwise he'd have enjoyed this level of form long before now, but evidently the potential was always there.
Comolli will not be missed at Spurs despite scouting and recruiting Gareth Bale in 2007, but he was perhaps more miss than hit in the transfer market which ultimately led to his departure.
They may have signed Payet under his watch, but how many more poor investments would have followed?