Tottenham Turn to Long-Term Target Charles De Ketelaere as James Maddison Faces 7 Months Out

Tottenham have made no secret of their admiration for Charles De Ketelaere in the past, and they are expected to reignite their interest in the Atalanta maestro, as James Maddison undergoes anterior cruciate ligament (ACL) surgery.

How Long is James Maddison Out For?

Tottenham’s pre-season has given fans reason to be optimistic, as the club embrace another managerial change with the arrival of Thomas Frank.

The former Brentford manager is yet to lose a game across Spurs’ five pre-season matches thus far, which includes a victory over Arsenal in the first north London derby to be played overseas.

However, their most recent result — a 1-1 draw against Newcastle — was overshadowed by a gut-wrenching injury with just four minutes left to play.

James Maddison, who missed a total of 11 games last season through injury, suffered a serious rupture to his ACL,  and will now be forced to undergo surgery. Typically, ACL injuries that require invasive surgery can keep players on the sidelines for between six and seven months.

Charles De Ketelaere is Tottenham’s Dream James Maddison Replacement

Tottenham owner Daniel Levy has earmarked considerable capital for reinforcements this summer, with the club in a healthy financial position following their Europa League victory last season.

Although that had largely been reserved for bolstering a leaky defense that conceded more goals than they scored in 2024-25, Spurs may now be forced into the market for a new creative midfielder.

With Maddison and Dejan Kulusevski sidelined, along with Son Heung-Min’s recent exit, Tottenham start the season without players who delivered 67 goal contributions in the previous campaign.

It leaves offshore sportsbooks questioning Tottenham’s ability to break back into the European spots, with Spurs now seventh in most experts’ estimations.

Tottenham appreciate that identifying a market opportunity, and negotiating for a player suitable enough to slot in immediately will be a tall order.

Fabio Paratici is expected to return to Tottenham after serving his 30-month suspension, but for now his continued role as a consultant is proving worthwhile. Reports this week suggest Spurs lodged a bid for Como’s highly sought-after midfielder Nico Paz, only for it to be rejected.

However, they hope groundwork laid already could help remedy the unforeseen situation in midfield, and Paratici’s Italian connection will be vital.

That groundwork relates to Charles De Ketelaere, whom Tottenham have been interested in before the Belgian arrived in Italy three years ago.

His two seasons at Atalanta have been fruitful, racking up 27 goals and 24 assists across both campaigns.

Given La Dea have already lost last season’s Serie A top scorer Mateo Retegui, and are expected to sanction the sale of Ademola Lookman to Inter Milan, luring De Ketelaere to north London will be a difficult operation.

FootItalia understands Tottenham are prepared to throw a considerable amount of cash at a replacement for Maddison, and De Ketelaere has been admired by the club since his formative years in Belgium.

With three years left on his contract in Bergamot, it will take a bid close to $70 million to pry him away this summer.