It is ironic that the man who has appointed Roberto De Zerbi to be Tottenham manager, just as the club faces its most critical seven games this century, is also partially responsible for one of the most successful managerial recruitments in Mikel Arteta, albeit for north London rivals, Arsenal. And even that didn’t start well. Vinai Venkatesham was blindsided when photographs of him emerging from Arteta’s house at 1.20am were published in a newspaper at a sensitive stage in negotiations. The man who is now Tottenham’s chief executive only found out he had been rumbled when the pictures went online and was mortified.

Venkatesham was part of a committee that settled on Arteta as a replacement for Unai Emery, and while it was a huge gamble to entrust a novice to a club the size of Arsenal, it was at least inspired, which is more than can be said for his hiring of Igor Tudor, a coach with no Premier League experience, to save Spurs. Now Venkatesham, along with the sporting director, Johan Lange, has settled on De Zerbi, which is similarly high risk.

Spurs can at least point to the fact that De Zerbi has been a highly...