Tottenham Hotspur supporters were left in shock earlier this week when it was confirmed that long-serving chairman Daniel Levy would be stepping down from his role at the club.

He spent more than 24 years in the position, since being appointed in March 2001, and played a part in Spurs winning two major trophies during that time, the League Cup in 2008 and the Europa League earlier this year.

Tottenham Hotspur chairman Daniel Levy, Technical Director Johan Lange and CEO Vinai Venkatesham

Speaking last month, before this announcement, Levy said: "I think it's one of those situations [in which] when I'm not here I'm sure I'll get the credit. When you come here and look at this wonderful [stadium], and the fact that other clubs are now trying to copy what we're doing, that should be a sign that maybe we did do something bold, and something right."

Perhaps that is now true. Supporters and the wider footballing community may look back at what he achieved as the chairman of the club, with the standout being that they were the most profitable 'big six' team during his tenure.

However, Levy was not perfect, no one is, and there were plenty of missteps along the way in North London, particularly when it came to making signings.

Daniel Levy's worst signings for Spurs

As ESPN recently noted, the English supremo was heavily involved in transfer windows, even when sporting directors were in place, and had a hand in every deal in and out of the first-team.

A quick glance at Levy's ten most expensive signings during his time as the club's chairman will tell you that he was far from perfect in the transfer market, albeit more than one person decides and acts on a signing.

Davinson Sanchez and Tanguy Ndombele immediately stand out in this list for the wrong reasons, whilst Dominic Solanke, Richarlison, and Archie Gray have been at the club for at least a year and are yet to prove they were worth the massive money spent on them.

Time will tell whether or not recent summer signings Mohammed Kudus and Xavi Simons will turn out to be good signings, particularly given that the latter is yet to play a game for the club.

Beyond the current top ten, you can also point to the £26m club-record signing of Roberto Soldado from Valencia in 2013, because the Spaniard only scored 16 goals in 76 matches in all competitions, per Transfermarkt.

Some players within the current first-team set-up could be considered among Levy's worst signings during his time as chairman, as he failed to provide recent managers with enough quality talent across the pitch.

One current Tottenham Hotspur player who was seemingly a poorly considered signing by the former Spurs chief is central defender Radu Dragusin.

Why Spurs should cash in on Radu Dragusin

In January of last year, Spurs reportedly splashed out a fee of up to £26m to sign the Romania international from Genoa to bolster Ange Postecoglou's defensive options.

As you can see in the table above, Spurs also made Dragusin one of the top earners in the squad on £85k-per-week, which is more than twice as much as Djed Spence, for example, earns (£40k-per-week).

Spence, who is currently in the England squad, has started all three matches in the Premier League this season and started 19 of his 25 outings in the division last term, per Sofascore.

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His emergence as an England international illustrates his rapid rise in North London and shows that he is a valuable member of the squad, which is why Dragusin earning so much more than him may be questionable.

The Romanian international has been out with an ACL injury since February, unfortunately, but his first year at the club did not suggest that he was on track to be a successful signing.

Radu Dragusin for Tottenham

Dragusin ranked within the bottom 4% of centre-backs in the Serie A for Genoa during the 2023/24 Serie A campaign for progressive passes per 90 (1.53) and the bottom 29% for pass accuracy (82.1%), per FBref.

This is why it was an odd signing to begin with for Spurs because they signed a centre-back who struggles playing out from the back to play in a progressive and risk-taking Ange Postecoglou side.

Tottenham Hotspur manager Ange Postecoglou looks dejected

The 23-year-old defender only made ten progressive passes and five progressive carries in his nine outings in the Premier League in his first five months in England, per FBref.

As you can see in the table above, the former Genoa star ranked poorly among his positional peers in a host of possession-based metrics in the Premier League across his 16 appearances in the division before his injury.

In December of last season, pundit Chris Sutton described Dragusin's decision-making as "terrible" in a 6-3 loss to Liverpool at home in the Premier League.

It is hard to disagree with that assessment when you consider that the central defender made four errors that led to shots or goals for the opposition in just 14 starts in the division in the 2024/25 campaign, per Sofascore.

Dragusin, to put it simply, does not look comfortable in a team that wants to have plenty of the ball and play out from the back in a league that is as intense as the Premier League, because of the speed of the press from opposition teams.

This is why the Romania international was among Levy's worst signings, because he seemed doomed to fail from the start, and why the club should look to move him on when he is back fit, as he has proven himself to be too much of a liability in possession.