Levy followed that up by brokering a deal believed to be worth over £6 million with newly promoted Watford for another midfield disaster, Etienne Capoue - a player former manager Tim Sherwood correctly predicted had no future with North Londoners.
While the deals in one respect represent an admission of failure and see the club making a loss, they show just why Levy is one of the most successful and longest serving Premier League chairmen.
A businessman at heart as well as a boyhood Spurs fan, Levy has always had a reputation for being ruthless and driving a hard bargain.
When it seemed inevitable that Gareth Bale would leave for a bigger club, Levy ensured he squeezed every last penny out of the situation, eventually getting a world record fee for the Welshman.
When Manchester United wanted Dimitar Berbatov, Levy made sure they paid top dollar to get their man and profited to the tune of £20 million.
'West Ham's our feeder club'
In the past he famously raided bitter rivals West Ham United for two of their star young players Michael Carrick and Jermain Defoe.
He got Carrick for just £3.5 million and ended up selling to Manchester United for nearly £20 million. It gave Tottenham fans great delight as they taunted their rivals for years with chants of 'West Ham's our feeder club'.
The Hammers vowed never to do business with the 53-year-old again back in January after he personally stopped Emmanuel Adebayor's deadline day move to east London at the 11th hour.
The Irons had been flying in the league and we're fourth after Christmas. But with injuries to Diafra Sakho and Andy Carroll they needed more firepower.
Levy, aware his club were dealing with a direct competitor, pulled the plug on the deal despite the fact the African star had been frozen out of the first team picture at White Hart Lane.
He could have got Adebayor's considerable wages off the books, as many a chairman would have been all too keen to do.
But he weighed up the situation and made a typically considered decision. In the end the Hammers struggled all the way to the end of the season without any goalscorers and plummeted to 12th. Spurs rose up and passed them on the way to finish fifth.
Bale windfall shows he doesn't always get it right
Levy doesn't always get it right, though, as was proved by the way the club squandered much of their Bale windfall cash on players that failed to make the grade in the Premier League.
When Levy does get it wrong though, unlike other club chairmen, he somehow manages to move players - many of whom have had their reputations tarnished - out and recuperate a good chunk of money in the process.
With Mauricio Pochettino in charge, though, Levy has a manager he can trust with the club's money.
And now Spurs aren't rushing into the transfer market for the sake of it with everyone knowing what they have to spend.
Their signings and targets seem more considered as the pursuit of Atletico Madrid right back Toby Alderweilder - who shone on loan at Southampton last season - proves (as per the BBC).
With Tottenham expected to be one of the busiest clubs during the summer window, one thing is for sure the club's transfer dealings could not be in many better hands.