Fikayo Tomori is unlikely to be emotional when he returns to Stamford Bridge Wednesday night in the Champions League. Calm and collected is the best way of describing the Milan centre-back. The impression is of a young man who does not like to get carried away, who knows his development as a footballer is far from over, and with that mentality there is every chance Tomori will approach the challenge of facing Chelsea with the same gracefulness that has typified his performances for Milan.
At the same time Tomori will undoubtedly have a point to prove when he plays against his former club. From a wider perspective, it is a chance for Milan to lessen Chelsea’s hopes of making it out of their Champions League group. On a personal note it is an opportunity for Tomori on two fronts: to push his case for inclusion in England’s World Cup squad and to make Chelsea regret not fighting harder to keep him.
It did not have to be this way. In different circumstances Tomori easily could have been putting on a blue shirt and preparing to mark Olivier Giroud Wednesday night. The irony is that the 24-year-old, who joined Milan on loan in January 2020, signed for them six months later and won Serie A last season, could have become a regular starter for Chelsea.
A lack of foresight has ended up costing Chelsea a lot of money. After Tomori was relegated to fifth-choice centre-back at the start of the 2020-21 season, forcing him to look for a fresh opportunity, the pathway soon looked clearer. Kurt Zouma was sold to West Ham in the summer of 2021 and Chelsea, having seemingly been in a position of strength, found themselves scrambling to sign centre-backs after losing Andreas Christensen and Antonio Rüdiger on free transfers this summer.
Yet Tomori, who rose through Chelsea’s academy and was brought into the first team by Frank Lampard in 2019, had gone. He did not fall out with Lampard, but the opportunities dried up. Milan made their move. They were long-time admirers of Tomori and his loan was sealed three days before Thomas Tuchel replaced Lampard.
Tomori was heading down a new path. He did not panic when he made his Milan debut as an early substitute during a Coppa Italia tie against Internazionale. Thrown in at the deep end after an injury to Simon Kjær, he took on Romelu Lukaku at San Siro, his performance drawing praise despite 10-man Milan losing in the last minute.
There would be no looking back. Tomori has embraced the experience of living abroad, learning Italian and becoming a firm favourite with Milan’s supporters. He quickly made himself integral to Stefano Pioli’s plans, clicking with Kjær, and made the loan permanent after helping Milan qualify for the Champions League for the first time in seven years.
It was a reward for Tomori stepping out of his comfort zone. His problem was never a lack of talent. The quality was clear while he was rising up the Chelsea ranks. He often played at right-back but always looked destined to move into the middle. Lower-league loans helped. Spells with Hull and Brighton were followed by Lampard taking him and Mason Mount to Derby County in 2018. Derby narrowly missed out on promotion, but Tomori was named player of the year by supporters.
At that stage it seemed Tomori’s next move would be to a Premier League side. Everton were interested, only for an opening to appear when Chelsea sold David Luiz to Arsenal just before the start of the 2019-20 season. Lampard had left Derby for Chelsea, who were under a transfer embargo, and he decided to use Tomori because of his performances in training.
The gamble paid off. Comfortable in possession, Tomori caught the eye with a stunning goal during a 5-2 win over Wolves. He used his speed to handle Mohamed Salah during a defeat by Liverpool. Under pressure during an away game against Ajax, he played his way out of trouble by leaving Hakim Ziyech on the floor with a clever turn.
But perhaps Tomori’s inexperience caught up with him. There were flaws in his game; occasional lapses in concentration. Tomori drifted to the margins. Milan, the club of Paolo Maldini and Franco Baresi, have made him a more mature defender. His tactical awareness has improved – playing alongside the experienced Kjær has helped, though there is also promise in Tomori’s partnership with the 22-year-old Frenchman Pierre Kalulu – and he has become stronger.
Equally Tomori, who signed a new five-year deal in August, has made Pioli’s dynamic young side better. His pace allows them to play a high line and he was key to Milan winning their first Scudetto since 2011 last season.
Leaving Chelsea has paid off. The only recent disappointment for Tomori was failing to play in England’s Nations League ties against Italy and Germany, raising doubts over his place in Gareth Southgate’s plans. One theory is that Tomori is paying the price for not playing in the Premier League. It makes his reunion with Chelsea, who visit San Siro next week, feel even more important.
Southgate will surely be looking at how Tomori handles Pierre-Emerick Aubameyang. Milan top their Champions League group with four points from two games, but they travel without a host of key players. The onus on Tomori is to step up and lead his team. He will need to hold his nerve.