De Zerbi eyes Etihad raid

Tottenham are preparing for a significant squad overhaul this summer. Following a season that left much to be desired, Roberto De Zerbi has signaled that while 12 players are secured for his long-term vision, the remaining squad is up for assessment. The Daily Mail reports that Spurs are identifying two Manchester City stars as primary targets for this rebuild.

The move is a tactical admission from the north London hierarchy. De Zerbi’s high-pressing, vertical system requires specific physical profiles, and the current squad has struggled to consistently execute his transition demands. By targeting players currently embedded in the Manchester City system, Spurs are essentially looking for talent that already understands a complex, modern positional structure.

The squad surgery

Beyond the interest in City personnel, Tottenham are balancing multiple fronts. The club is actively working through a shortlist that includes defender Yan Diomande and backup keeper Karl Darlow. Perhaps most urgent is the internal focus on Joao Palhinha, whom the club is desperate to retain as a defensive shield for their midfield.

This reliance on established talent is a departure from the club's typical focus on high-upside prospects. It suggests that De Zerbi has successfully lobbied for Premier League-ready reinforcements, likely to avoid the slow starts that hampered his arrival earlier this season. While the ambition is clear, the financial trade-off for bringing in established winners from a rival like City could tighten the budget for other areas.

Tactical fit and potential pitfalls

The core challenge for De Zerbi remains defensive stability. Tottenham’s inability to manage leads was a defining narrative of their recent campaign, and adding players groomed in City's controlled environment could prove beneficial. However, City's stars often arrive at new clubs with outsized wage demands, potentially creating a bottleneck in the dressing room wage structure.

Critics will look at the history of such transfers and wonder if these individuals can replicate their performance in a less structured environment. If the move happens, these players will immediately be tasked with anchoring the team. The pressure will be immense, especially with the 2026 World Cup beginning on June 11, which will inevitably stall negotiations for several weeks.

Milan’s parallel chaos

While Tottenham map out their path forward, AC Milan are dealing with a total institutional collapse. As CorSport notes, the entire hierarchy from Massimiliano Allegri to Giorgio Furlani is under scrutiny after a disastrous season. The contrast between Tottenham’s calculated, albeit risky, pursuit of new talent and Milan’s internal fire sale is stark.

Management at Milan is undergoing a brutal transition, with Zlatan Ibrahimovic and Calvelli taking the lead in a total rebuild, as Sky reports. Expect four major departures from the Italian side as they try to salvage their identity. This volatility in the market from one of Europe’s biggest clubs could inadvertently help Tottenham, as clubs might compete for the same pool of available talent should the market become flooded.

Probability and outlook

The probability of this deal coming to fruition sits at medium. De Zerbi has influence, but negotiations with the current English champions are never straightforward, especially with a £0 starting point for official bids today. Every day counts between now and the season-opening matches in August.

If these transfers are finalized by early July, it would represent a massive technical win for the coaching staff. It would signify a move toward a more disciplined, high-IQ version of Tottenham’s setup. Barring any late-window shifts, these arrivals would ideally command a place in the starting XI within 4 weeks of training, though the adjustment period for any new arrival is a constant concern.