Deadline day has produced some strange transfer stories over the years, but few are quite as eyebrow-raising as this one. According to Fabrizio Romano, Tottenham are working on a double deal with fierce London rivals Chelsea, looking to bring in both winger Mykhailo Mudryk and center-back Tosin Adarabioyo before Tuesday’s window slams shut. Spurs doing business with Chelsea is rare enough on its own. Doing it twice in one afternoon is the kind of twist that makes deadline day must-watch television.
Why Roberto De Zerbi Wants Mykhailo Mudryk
The Mudryk piece of the puzzle traces back to Roberto De Zerbi’s admiration for the Ukrainian winger, a player he knows well from their overlapping paths in football. Spurs’ interest reportedly emerged after complications developed around a separate deal for Iliman Ndiaye, pushing Tottenham to pivot quickly toward Mudryk instead. Chelsea, for their part, had been steering Mudryk toward a move to Strasbourg and had already turned down interest from Leeds United, but the winger himself wants to stay in London, and Spurs are willing to give him that chance on loan.
It has been a rocky few years in West London for Mudryk since his blockbuster arrival from Shakhtar Donetsk, and a fresh start across the city, even a temporary one, could be exactly what his career needs right now.
Tosin Adarabioyo Set for a Permanent Switch
The second half of this double deal looks even more straightforward. Tosin Adarabioyo, who joined Chelsea on a free transfer from Fulham in 2024, simply is not part of Xabi Alonso’s plans at Stamford Bridge this season. With Kevin Danso having asked Tottenham for an exit in search of regular first-team minutes, De Zerbi needed a like-for-like defensive body, and Chelsea’s centre-back has been given the green light to complete a permanent move, with personal terms already agreed and a medical lined up on deadline day itself.
The Bigger Picture for Both Clubs
Context matters here. Tottenham have endured a rough start to the season, losing their opening two Premier League matches against Brentford and Newcastle United, and De Zerbi has been aggressive in the market as a result, having already added the likes of Andy Robertson, Sandro Tonali, and Omar Marmoush this summer. A move for Cody Gakpo also fell through after the Liverpool forward opted for Manchester City instead, leaving another gap that Spurs are scrambling to fill in the closing hours of the window.
For Chelsea, this is simply squad trimming with purpose. Alonso is reshaping his defense and forward areas simultaneously, having already brought in goalkeeper Emiliano Martinez while sending Robert Sanchez toward a move to Como. Moving on both Mudryk and Adarabioyo in one swoop clears space and raises funds as the Blues continue reshaping their squad for the new era.
What Happens Next
With the clock ticking toward Tuesday’s 11pm deadline, both deals are reportedly progressing at pace, though as always in transfer windows, nothing is final until it is officially announced. If completed, this double swap would rank among the more unexpected transfer stories of the entire summer, proving once again that when deadline day arrives, even the fiercest rivals can find a reason to do business.
