From Krunic to Vasquez: The 35 signings of the Maldini and Massara era at Milan

The Paolo Maldini and Ricky Massara era at AC Milan has officially come to a close as the pair were sacked from their positions as technical director and sporting director respectively.

Through a statement on their official website Milan announced Maldini’s departure and one is expected to follow for Massara too, leaving the Milan world in shock given we are less than 48 hours on from the end of the 2022-23 season.

The duo formed a close relationship during their four years together and have been given a lot of credit for building the young core that Milan have now, leading to a Scudetto victory, a Champions League semi-final this season and three consecutive qualifications for the competition.

Maldini completed 34 signings during his time as the technical director (from summer 2019 onwards), and FootballItalia have listed them:

Summer 2019

➤ Rade Krunic from Empoli – €8.6m
➤ Leo Duarte from Flamengo – €10m
➤ Theo Hernandez from Real Madrid – €22.8m
➤ Rafael Leao from Lille – €29.5m
➤ Ismael Bennacer from Empoli – €17.2m
➤ Ante Rebic from Eintracht Frankfurt – €7m

January 2020

➤ Zlatan Ibrahimovic – Free agent
➤ Alexis Saelemakers from Anderlecht – €10m
➤ Asmir Begovic from Bournemouth – Loan
➤ Simon Kjaer from Sevilla – €3.6m

Summer 2020

➤ Pierre Kalulu from Lyon – €1m
➤ Brahim Diaz from Real Madrid – loan
➤ Sandro Tonali from Brescia – loan then €19.5m
➤ Ciprian Tatarusanu from Lyon – €1m
➤ Jens Petter Hauge from Bodo/Glimt – €4.8m
➤ Diogo Dalot from Man Utd – loan

January 2021

➤ Soualiho Meïté from Torino – loan
➤ Fikayo Tomori from Chelsea – loan then €31m
➤ Mario Mandzukic – Free transfer

Summer 2021

➤ Mike Maignan from Lille – €15.4m
➤ Alessandro Florenzi from Roma – loan then €2.7m
➤ Olivier Giroud from Chelsea – €3m
➤ Fodé Ballo-Touré from Monaco – €5.4m
➤ Tiemoue Bakayoko from Chelsea – loan
➤ Junior Messias from Crotone – €5.5m

January 2022

➤ Pietro Pellegri from Monaco – loan
➤ Antonio Mirante – Free transfer
➤ Marko Lazetic from Red Star – €4.5m

Summer 2022

➤ Yacine Adli from Bordeaux – €10m
➤ Divock Origi – Free transfer
➤ Charles De Ketelaere from Club Brugge – €32m
➤ Malick Thiaw – €5m
➤ Aster Vranckx – Loan with option to buy from Wolfsburg
➤ Sergino Dest – Loan with option to buy from Barcelona

January 2023

➤ Devis Vasquez from Guaranì – €470k