Levy is known around the footballing world as one of the toughest negotiators, a trick that has seen him reap as much revenue as he can from potential sales.
It seems Real president Florentino Perez will be forced be play cat and mouse with Levy again, as the club sets their sights on Pochettino becoming Zinedine Zidane's successor.
However, Perez has good experience dealing with the London club, and will have to draw on his experience from talks over Van der Vaart, Modric and Bale if he is to get what he wants.
Van der Vaart is the exception to the rule. Instead of players swapping London for Madrid, the former Netherlands international did it in reverse and Levy got a shewd purchase for €10million.
Two years at the Bernabeu was followed by two years at Spurs, where he scored 28 goals in 77 appearances - a decent return for an attacking midfielder.
Two years later and the two clubs were back at the negotiating table. This time, Madrid were eyeing up two of Tottenham's players: Luka Modric and Gareth Bale.
Both were long-drawn out sagas. Levy only gave the green light for Modric's departure on August 27, after he had identified an adequate replacement
Bale's came four days later and at a staggering fee of €100million at the time. It was down to Levy as to why Spurs were able to eek so much profit out of 'Los Blancos'.
Now it seems we could be in store for a similar soap opera with Tottenham's current manager Mauricio Pochettino.
Following Zidane's shock departure, the Argentine has been considered the favourite to take over in Madrid. Although, recent speculation has put that somewhat in doubt.
However, as the purchases of Bale and Modric prove, Levy may be a tough nut to crack but he does have his breaking point somewhere and it could come down to how much Perez is prepared to go to battle to be able to land his man.
If Perez rolls up his sleeves and get down and dirty, Pochettino could be standing in the technical area next season...