According to Real Madrid specialist journalist Ramón Álvarez de Mon, Mourinho has specifically asked the club to explore the possibility of signing the 24-year-old Italian international, attracted by his ability to play both as a left-back and a centre-half.
Calafiori joined Arsenal from Bologna in the summer of 2024 for £42 million and has become a key figure in Mikel Arteta's squad. He played a significant role in Arsenal's first Premier League title in 22 years and holds 65 appearances for the club across two seasons.
There is a particular subplot to this pursuit. Mourinho himself was in charge at AS Roma when the club sold Calafiori to Basel for approximately £1.5 million in 2022. The Italian's subsequent rise — Bologna, Arsenal, full Italy international — has been one of the notable development stories of European football in that period.
Mourinho is now ready to pay considerably more than £1.5 million to bring him back into his orbit.
AS reported that Mourinho values versatile defensive profiles capable of operating across multiple positions along the defensive line, and that the pursuit of Josko Gvardiol of Manchester City has been assessed as too difficult. Calafiori's profile fits the criteria more cleanly and, crucially, at a more manageable cost.
Real Madrid have already secured defensive reinforcements in the form of Liverpool's Ibrahima Konaté, who arrives on a free transfer, and Inter Milan's Denzel Dumfries, whose release clause of £20 million was activated.
Calafiori's Arsenal contract runs until 2029, which means the Gunners hold significant leverage. Whether the Italian himself — a Premier League champion who missed the Champions League final through injury — would entertain a move to Madrid is not yet established.
The approach may be a difficult one. But Mourinho has previous on convincing defenders that the Bernabéu is worth the upheaval.