Dutch supremo is reportedly being chased by Spartak Moscow, leaving Tottenham with a pressing decision to make on whether they want him in charge next year.
Between sacking managers that had Spurs sitting pretty in the top five, selling the club's top players to a side he confirmed the North Londoners were in a 'strategic partnership with', and appointing a director of football who has presided over a quite disastrous couple of transfer windows, Levy has overseen Spurs slip from the Premier League elite, while Liverpool and Everton have both moved above them.
Both Merseyside clubs have spent considerably less than Tottenham over the last few seasons, yet are now two of the most attractive sides in the league, while Levy's side, reinforced with £100 million worth of international players last summer, are playing like strangers.
And after another Spurs capitulation to Liverpool left Tim Sherwood under even more pressure, talk once again turned to Tottenham's rumoured interest in Netherlands boss Louis van Gaal.
The Dutchman has an exemplary record at some of Europe's top sides, winning trophies with Ajax, Barcelona and Bayern Munich.
But further speculation about Van Gaal has seen reported interest from Russian giants Spartak Moscow, who themselves are lingering outside the Champions League places.
The Metro also reports that Manchester United are within Van Gaal's thoughts, as he looks towards his next role following the conclusion of Holland's World Cup tournament.
Despite comments from Dutch legend Ruud Gullit indicating that he thought Van Gaal would end up at Spurs, as well Van Gaal himself saying that he was looking to manager in the Premier League, nothing is certain right now.
The onus is clearly on Daniel Levy to make a decision as quickly as possible on whether he wants a new man in charge at Spurs next year, as well as how high up that list Van Gaal is. He has to move quickly to ensure his fabled business acumen isn't sullied further by an inability to secure the most attractive candidate.