Day 50 in the job and Ange Postecoglou woke in Singapore to find, on the other side of the world, the billionaire responsible for bankrolling the modern Tottenham now stood accused of insider trading.
Joe Lewis built the empire containing Spurs and the fact that he had the foresight to remove his name from over the door before this fraud investigation reached this critical stage will do little to ease any misgivings.
Lewis remains the moneyman at the top of the club. Earlier this week, sources revealed the 86-year-old had personally intervened to tell chairman Daniel Levy to sell Harry Kane if he is unwilling to sign a new contract this summer.
So here was one more cloud of uncertainty drifting across Postecoglou's horizon since his arrival. One he had no right to have expected. One more lesson in what has become a crash course in the perils of managing Tottenham. Things rarely go smoothly.
First, the transfer market. Despite the desperate need for defensive reinforcements, they have only goalkeeper Guglielmo Vicario, creative midfielder James Maddison and promising winger Manor Solomon.
Deals he hoped were close, such as Micky van de Ven from Wolfsburg and Ashley Phillips from Blackburn, remain incomplete, although still alive, and players they were hoping to move on are still there.
Davinson Sanchez is not overly enamoured with the prospect of a move to Russia, despite Spurs accepting a bid from Spartak Moscow. So with the new Premier League season set to start a week tomorrow(FRI) with the defensive unit very much as it was.
Then, of course, there is Bayern Munich's public pursuit of hero Kane. On Saturday, in Bangkok, Postecoglou found himself ambushed by a reporter from the German newspaper Bild waving about a Bayern
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