When Enzo Maresca joined Chelsea from Leicester City in July 2024, one of the biggest challenges was managing the massive squad of 43 professional players eligible for the first team at the start of the season. With the winter transfer window approaching, the Italian coach has left the door open for a $60M signing to depart due to a lack of playing time.

One of the significant acquisitions during Roman Abramovich’s ownership was Ben Chilwell. The left-back, who had established himself as one of the Premier League’s best during his time at Leicester City and with the England national team, joined Chelsea in August 2020 for €50M ($60M at the time). Despite his early promise, Chilwell has struggled to find a place in Maresca’s system, prompting speculation about his future.

In Friday’s pre-match press conference, Maresca didn’t shy away when asked about unhappy players in the squad. “There are players that unfortunately didn’t play a lot with us in all the competitions, like Chilwell, like Carney (Chukwuemeka). Probably they are the first ones who want to leave because they work every day, they train every day, and they want to play games. If they don’t play games, probably they’re thinking about leaving.”

The contrast between Chilwell’s role this season and last season is striking. Despite missing significant time during the 2023-24 campaign due to injuries, the left-back was still a key starter under Mauricio Pochettino, logging 1,172 minutes across 21 games, and being the second captain of the team.

This season under Maresca, Chilwell’s situation has been drastically different. Despite remaining fit and training consistently, he has been relegated to the sidelines. Excluded from Chelsea’s UEFA Conference League roster, Chilwell has only played 45 minutes across all competitions this season—coming on as a second-half substitute in a 5-0 EFL Cup win against AFC Barrow.

Early signs of Chilwell’s marginalization

Maresca hinted at Chilwell’s diminished role during the preseason. When asked about the left-back’s position, the coach said, “The reason he did not play versus Inter was because, with Chilly (Chilwell), it is quite clear. Even though I love the way he is, the problem is that he is struggling a bit to find the right position.

“This morning we had 22 players training and if you ask all of them they will say they want to play against City on Sunday. But that is impossible. When you train every day and do not get any minutes it is not good for them or for me. I need to make a decision and probably it is better to leave and go and get minutes. The transfer window is open so we’ll see what happens,” Maresca said, already hinting Chilwell to look for a future out of Chelsea.

More Chelsea players on the way out

Chilwell isn’t the only player facing an uncertain future at Stamford Bridge. According to Fabrizio Romano, Carney Chukwuemeka and Cesare Casadei are also exploring January exits in search of more minutes. Meanwhile, Marc Guiu’s situation remains unresolved.

Casadei has attracted interest from multiple Serie A clubs and could leave on loan or through a permanent transfer. Chukwuemeka, on the other hand, has suitors across Europe, including Italy. AC Milan, who pursued the midfielder during the summer, could reignite their interest in January.