Tottenham's Transfer Window: De Zerbi's Strategy and Maddison's Status

Roberto De Zerbi walked into the media room at Hotspur Way with Newcastle on the horizon and the transfer window snapping shut behind it. One eye on Saturday night, the other on Tuesday at 11pm. That’s the reality of Tottenham Hotspur’s week.

Spurs have already thrown more than £300 million at this squad over the summer and brought back close to £150m in sales. Heavy spending, heavy churn. Yet De Zerbi made it clear the door has not closed.

“Can be possible, out,” he said when asked if players could still leave. The phrase was blunt, but the meaning was sharp. This squad is not locked in. Not yet.

He didn’t dress up the market, either. “In the transfer market, it is crazy, and we have to be able to find the players if some players go out to make another player in. I don't know. It's different now. The transfer market is crazy. You can't understand it.”

The pressure finally told in his admission that he still sees one gap. “I didn't expect a transfer window like we have done. I think we can do one player more in one specific position.” No name, no hint of the role, but a clear message: Tottenham are still in play.

Dinner, decisions and alignment at the top

On Thursday night, the talking shifted from the training pitches to the dinner table. De Zerbi sat down with the club’s hierarchy – the owners, sporting director Johan Lange and chief executive Vinai Venkatesham – to map out the final days of the window.

“Yesterday we went to dinner with the owners, Johan and Vinai, and we spoke about this,” he revealed. “All of us are on the same page and a very good connection.”

It was a telling line. For all the chaos of the market he describes, De Zerbi insists the internal picture is ordered. Strategy, not scramble.

While Lange works the phones and the numbers, De Zerbi’s focus is Newcastle. But his team sheet still depends on medical reports and transfer calls.

Maddison pain, but hope for Newcastle

At the top of that list sits James Maddison. The playmaker fractured his shoulder in the 3-0 defeat at Brentford on the opening weekend, a worrying sight for a player central to Spurs’ creativity.

The update this time carried more optimism than fear.

“James Maddison has not a big problem,” De Zerbi said. “Just pain in his left shoulder. He's working, but I don't know if he's available for tomorrow.”

So there is hope, but no guarantee. Maddison is pushing, the staff are assessing, and Tottenham will wait as long as they can before deciding whether their No. 10 can be thrown straight back into a high-intensity Premier League night.

De Zerbi also suggested Mohammed Kudus could come into the frame. No fanfare, no big build-up, just a quiet indication that another attacking option might be ready to join the matchday group.

Pape Matar Sarr and the late-window tension

If some players are edging closer to the pitch, others hover closer to the exit. Pape Matar Sarr sits right on that line.

“Pape is good,” De Zerbi said. “We have to see in the last days of the transfer market what can happen with him.”

It was a careful answer but not a closed door. Sarr is fit, available, but not entirely certain to be a Tottenham player when the window locks.

De Zerbi stressed the importance of honesty in these conversations. “I've been very clear with all the players. If you speak clearly, you can't expect surprises. The players who wanted to leave have left. We maybe have some players who want to leave, and they are waiting; we are waiting for an offer.”

That is the tension of this stage of the window. Players waiting. Clubs waiting. Managers trying to prepare for a game knowing that Tuesday night could still reshape their dressing room.

An “emotional project” under construction

Strip away the numbers and the noise and De Zerbi keeps coming back to one idea: commitment.

“You have to feel proud to stay here,” he said. “It's an emotional project we are building with new players.”

Pride, emotion, and a squad in flux. Tottenham have spent big, shifted big names out, and still want one more signing in a specific area. A few could yet depart. The manager wants only those who truly buy into what he’s building.

Newcastle arrive next, then the window slams shut. By Wednesday morning, De Zerbi will know exactly who has chosen to stay and fight for that project – and who has stepped away from it.