The results showed how good AC Milan’s transfer windows were in the previous two seasons – the return to the Champions League and the surprising title last season.Paolo Maldini and Ricky Massara built a championship team for relatively little money and brought in Tonali, Tomori, Brahim Diaz, Giroud, Maignan, Kalulu, Messias, Florenzi… True, there were also flops such as Bakayoko, Meite, Mandzukic or bringing in youngsters talents like Balo Toure, Hauge, Pellegri, Adli, Lazetić who did not turn out to be ‘bullseyes’. But the general impression was that Milan made a significant step forward and progressed with the 125,000,000 euros invested in two years.When, after the Serie A title, a new breakthrough and investments were expected that would elevate Milan to a higher class, failures followed. Thanks mainly to the change of ownership in the club and the chaotic situation when Maldini and Massara’s hands were tied and their contracts expired, Milan missed a significant part of the transfer window and then the new owners did not give the money they promised. The title was “rewarded” with only 50,000,000 euros for reinforcements. And the director’s tandem missed almost every talent they wanted to sign…##EDITORS_CHOICE##The current season in Serie A showed that, and the lousy impression was masked by reaching the semi-finals of the Champions League, where Milan will most likely face the city rival who taught him a lesson and showed that they are a class above. Now Milan need that qualitative jump that they will have to make in the transfer window in order to raise the level and move from the point of stagnation.Most of the money invested last summer went to bring Charles De Ketelaere from Club Brugge, a bet on which Maldini and Massara threw almost everything. They believed that they were getting a capital player who would soon make a difference and become one of the pillars of the team. But they got nothing. The Belgian, along with Richarlison, is probably the worst reinforcement of the season in the “top five” leagues. For 32,000,000 euros, he brought zero goals and zero assists in 1,415 minutes on the field and lately he is not even an option in important games. Milan will not give him up; it is an expensive investment, they will try to wait for him like they did with Sandro Tonali and will not let him go on loan even though Monza showed interest. But for now, it doesn’t look good…Other summer signings such as Aster Vranckx, Divock Origi and Sergino Dest were also ‘failures’. Only the young German stopper Malick Thiaw showed that he could be counted on.Milan now need a transfer window completely opposite from the last one and significant changes are already being announced. Gazzetta delo Sport presented a list of names for departures and arrivals.Doesn’t want to lose African players durng AFCON; Napoli president has a new ideaThe biggest deal was done by signing a new contract with the best player Rafael Leao. He was the priority and until that knot was untied, all other things were put aside. Milan can finally start the summer transfer window…Departing players are expected to clear the payroll by around €25,000,000 per year, which was their gross salary. Of the 10 highest-paid players at the club, four could leave. The biggest problem is Divock Origi, currently the highest-paid player in Milan along with Theo Hernandez (both have 4,000,000 net). At least until Leao’s new contract kicks in. The Belgian of Kenyan descent came as a free agent from Liverpool and completely disappointed. Milan would be happy to get rid of him at least through a loan, but it is difficult to find a club that will cover his salary, although there are rumors about a potential deal with one of the Turkish clubs. After Origi and Hernandez, the highest paid in Milan is the third right back Sergino Dest, whose loan from Barcelona is expiring. They can’t wait to see his back considering that he hasn’t shown anything in ten matches. The loan expires for the useless Bakayoko, and the end of the era has come for Ante Rebić, who has two years left on his contract and Milan will try to sell him because he has been on a downward trajectory for a long time. The four of them cost 20,000,000 euros per year without bonuses.Brahím Díaz on loan deal with AC Milan expiring in June: “Return to Real Madrid? I’m only focused on Milan now. #transfers I want to do my best here, I want to give it 100% of my energies”, tells Marca. pic.twitter.com/JWTOCyjCPH— ͏ Mohamed ✆ (@RMreports) May 9, 2023 The contracts of veteran Ibrahimovic and backup goalkeepers Tatarusanu and Mirante expire. They will not be extended. Neither did the loan of Belgian midfielder Vranckx from Wolfsburg. They are looking for a solution for the young French midfielder Yacine Adli, who did not get many chances under Pioli, and the club would like to loan him somewhere because they still believe in the development of his talent. Left back Fode Balo Toure will be released if anyone wants him. And that would be it for departures.Milan’s next task after Leao’s situation is to resolve the one with Brahim Diaz, who is on loan from Real Madrid, and to negotiate a new purchase price instead of the pre-agreed one of 22,000,000 euros. Milan hopes that Real will agree to the offer of 15,000,000.And as far as arrivals are concerned, Maldini and Massara have a broader list from which the main reinforcements should be sought. Striker, right winger and midfielder are essential.The departure of Ibrahimović and the possible departures of Origi and Rebić open up places for one or two attackers. Alvaro Morata from Atlético is the first choice, but it depends on the wishes of Madrid whether they will offer him a new contract since his current one expires in 2024. Along with the Spaniard, Milan also want Marko Arnautović, who is stranded in Bologna. His salary is not small, around 3,000,000 euros net, but the compensation would be symbolic and fits into Milan’s financial projections. He could make a difference in Serie A.🚨Loftus Cheek is one of the names that AC Milan appreciated for the midfield.The contract of the 🏴 player expires in 2024 and #Chelsea will try to sell him in the summer.The transfer fee shouldn’t be an issue, instead the salary could represent an obstacleVia @RudyGaletti pic.twitter.com/a1zONzaQ8D— Chelsea Express (@Chels_Express1) May 7, 2023 For the position of the right-wing, a player with different characteristics than Saelemaekers and Messias is wanted, offensively and technically more powerful. Milan’s long-standing desire is the gifted Carney Chukwuemeka, whom Chelsea took from Aston Villa this summer as one of the biggest talents in island football, but he does not have enough space and minutes in the fierce competition. As in the case of Diaz, Milan could arrange a loan. Or as they already did with the Blues in the case of Fikayo Tomori and bought him out at the end of his loan.The solution for the midfield problem could also come from Stamford Bridge. This is Ruben Loftus Cheek. Under Maurizio Sarri, he used to be standard at Chelsea; he played a lot under Thomas Tuchel, but with Potter and Lampard, his playing time was reduced and his prospects don’t look rosy either. He could follow in the footsteps of his friend Tomori, who is urging him to try out for San Siro. The alternative is Argentine midfielder Exequiel Palacios from Leverkusen.A lot depends on the finish of the season. Placement in the Champions League would provide a massive financial boost for the upcoming transfer window.SERIE A – MATCHDAY 35Friday21.45: (1.79) Lazio (3.60) Lecce (5.70)Saturday 16.00: (5.30) Salernitana (3.60) Atalanta (1.73)19.00: (3.80) Spezia (3.45) Milan (2.04)21.45: (1.48) Inter (4.50) Sassuolo (7.00)Sunday 13.30: (2.47) Verona (3.10) Torino (3.30)16.00: (5.00) Monza (3.70) Napoli (1.84)16.00: (2.09) Fiorentina (3.60) Udinese (3.90)19.00: (3.05) Bologna (3.10) Roma (2.55)21.45: (1.43) Juventus (4.60) Cremonese (8.00)Monday 21.45: (3.20) Sampdoria (3.45) Empoli (2.40)***odds are subject to change***