A move for Sebastian Kehl reportedly fell through when he was alarmed by De Zerbi's level of control.
The manager's volatile nature raises questions about the wisdom of entrusting him with such a consequential window.
What Is Tottenham's Identity?
The spending spree highlights a deeper issue: Tottenham have never settled on a clear identity.
Under Levy, they oscillated between frugality with young players, big-name managers, and underdog football.
Now, they are acting like a luxury brand, but without addressing key gaps like a replacement for Harry Kane or Son Heung-min.
The departures of promising youngsters Luka Vuskovic and Lucas Bergvall further undermine long-term planning.
In the new squad-cost-ratio era, this summer's spending will limit future windows. Yet as long as Tottenham avoid relegation, they can continue this cycle.
De Zerbi is a great coach but volatile and replaceable. The club's aim seems to be entertainment and the illusion of progress, rather than sustained success.
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For a club that is the ninth-richest in the world, the question remains: what is the point of Spurs?