Santiago Gimenez in action for AC Milan, looking at a circular inset of Roberto De Zerbi.
Santiago Gimenez and Roberto De ZerbiImago

Tottenham move perfect for Santiago Gimenez thanks to Roberto De Zerbi record

Cameron Smith

Correspondent AUTHORITY Sports journalist with experience at Football League World, Bulinews.com, and VAVEL; Birmingham City University graduate. FOCUS Statistical analysis, data deep-dives, and tactical coverage across the Breaking Media network. THE INSIGHT Cameron utilises data and a network of club contacts to deliver verified, stat-driven insight. He provides the analytical foundations behind the headlines to ensure fans understand the numbers shaping their club.

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Tottenham are reportedly interested in AC Milan forward Santiago Gimenez in a move that could make total sense.

It was outlined last month that the Lilywhites were tracking the Mexican, who has endured a difficult spell with the Milanese giants.

Now, Italian outlet Calciomercato report that the forward has been offered to Spurs, with it unclear whether this is a permanent or loan deal.

Currently on home soil at the World Cup, the 25-year-old is looking to recover from an under-par season in Milan.

Spurs themselves are also aiming to bounce back after securing their Premier League safety on the final day of the campaign.

And as the pair look to do this, the Tottenham Hotspur Stadium could just be the best place for Gimenez given Roberto De Zerbi's own record.

Roberto De Zerbi has proven himself as a developer

Making his European breakthrough at Feyenoord, the Mexican established himself as a rising star on the continent.

Scoring 65 times and registering 14 assists across 105 matches, Gimenez would move on to a disjointed AC Milan side in January 2025.

Following the move, he would score six times in the second half of the season, and looked like the man set to lead the Rossoneri into a new era.

Instead, things have gone disastrously under Massimiliano Allegri, after suffering an injury in the early days of the 2025-26 campaign.

In just 896 Serie A minutes, he has failed to score, while adding two assists to his name.

As a coach, though, De Zerbi has proven he can rescue talent before, with his platforming of Manuel Locatelli at Sassuolo seeing him star at the 2021 European Championships for Italy, before the Milan reject earned a move to Juventus.

At the same time, he has nurtured Moises Caicedo, Alexis Mac Allister, Levi Colwill and more at Brighton, while also beginning to get the best out of Xavi Simons and Mathys Tel in the early days of his Spurs tenure.

The 46-year-old does have a more rigid and controlled style of play, but he has proven fantastic at profiling his players.

While he is dramatically out of form, the talent and goalscoring expertise are most definitely there with Gimenez - playing in an attacking system could see him finally reach that next level in North London.

Santiago Gimenez in action for AC Milan, looking at a circular inset of Roberto De Zerbi.
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Thus far, there does seem to be a theme of common sense surrounding the links.

Across De Zerbi's tenure, similar issues have persisted both up top, and in midfield, with the approach very much being 'square pegs in round holes' as a result of a razor thin squad.

More than anything, this is a testament to De Zerbi, who was able to put the required points on the board with such a squad.

Spurs are seemingly targeting their weak spots, including at centre-back, where Marcos Senesi has been secured, while they remain interested in Jan Paul van Hecke.

Operating with common sense, Spurs look set to address key areas of De Zerbi's squad, who could benefit from a strong pre-season with the bulk of his side together in one place.

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