Daniel Levy came under fire from Tottenham supporters last season, with several protests held against the chairman.
One of the reasons behind the protests was a lack of spending by the North London club, with poor performances only fuelling anger.
However, this transfer window is following a different rhetoric as the Lilywhites close in on a couple of landmark deals.
Mohammed Kudus has sealed his move to Spurs, with his heart set on switching East London for Hotspur Way very early on.
Champions League football triggers mass Tottenham spending
Tottenham are also closing in on a deal for Nottingham Forest captain Morgan Gibbs-White after triggering a £60million release clause in his contract.
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It comes after it was suggested that ENIC may invest more into Spurs, as cash levels supposedly hit dangerous levels at the Tottenham Hotspur Stadium.
Football finance expert Dan Plumley, speaking exclusively to Tottenham News, has provided insight into why the North London outfit are set to spend significantly.
“No fan is going to get overly annoyed if there’s a change in tone and investment is forthcoming, are they?” he said.
“There’s obviously the bigger picture and the backstory with Spurs and the ownership group, and what I would tag into that is it’s always interesting when these changes of narratives perhaps come along around times where things have just got a little bit better.
“Of course, what I’m referring to there is Champions League football next season, so that is going to bring with it a huge windfall in the region of perhaps £86-130million, even at the kind of prudent estimates, so that brings with it optimism to look to invest and to spend as well.
“It’s always about the context of where the club’s at, but I think ultimately if they are going to put in some fresh investment despite the trials and tribulations, most fans certainly in the short to medium term are going to be looking at that as a positive.“
Gibbs-White set to sign, but could Spurs spend more?
If Tottenham can tie up deals for Kudus and Gibbs-White, then they would likely spend north of £100million on two players.
However, would Levy be able to follow that up with more transfers? And, if so, who?
Much of that could depend on sales, with Cristian Romero and Yves Bissouma linked with a Spurs exit.
Both would likely garner substantial fees, particularly for Romero, who is wanted by Atletico Madrid.
Yoane Wissa looks to be another possible arrival and has been touted for a reunion with Thomas Frank.