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What if AC Milan hired someone else as a manager, made some different transfers, held on to some promising players a little longer?
(Just like with my last 2 “What if?”)
I’ll only mention my major alternative moves, changes, and alternate histories. Keep in mind mistakes will still made because no board or manager is perfect. (For example: Pierre Aubameyang, Pirlo and Thiago Silva are still also sold.) Feel free to ask any questions or add input. I’m happy to explain or add to the story.
In this timeline…
2016-17
AC Milan are in search of a manager once more, Vincenzo Montella is more of a fall back manager. Instead Gian Piero Gasperini is offered the job 1st and given a better offer than what Atalanta BC offered him. He graciously accepts and so begins AC Milan’s New Age! Gian Piero Gasperini would begin to implement his 3-4-3 formation and variations.
Not having much of a transfer budget to work with, Milan heavily target free agent Zlatan Ibrahimović who chooses AC Milan over Manchester United, taking on the challenge of returning Milan to its former glory. Also receiving a better deal. (*Alt move* Regardless he’d have a year left in contract with Man U the following year: AC Milan would pay the money necessary to buy him then.)
**Gasperini chooses to keep Stephan El Shaarawy and use him in the CF role of his system.(Although later acquiring better options for the position he still keeps El Shaarawy for depth.)
Mario Pašalić would still come to Milan on loan and would later be purchased.
Gasperini seeing Josip Iličeić’s potential chooses to buy him earlier than he did with Atalanta. (Becoming a key stater at AC Milan over the years.)
**Gian Piero Gasperini leads AC Milan to a 4th place finish. (just as he did with Atalanta) AC Milan however, do find more success in the Coppa Italia beating Juventus in their knockout match. Having taken out this giant AC Milan continue their momentum going on to win the Coppa Italia.
Having a promising start, Gasperini is given another year to lead Milan to the Champions league.
2017-18
This season AC Milan still have a very large budget. **With this being such a pivotal transfer window for success, it’s almost entirely different. (Most transfers each season would be different with Gian Piero Gasperini at the helm. Again I’ll only mention major moves.)
This time AC Milan use the large budget to poach some big Serie A stars, but this time from Napoli. Milan throw big money at Lorenzo Insigne and Kalidou Koulibaly. (Insigne would play the same role Gomez played for Gian Piero Gasperini in real life.)**With Insigne at Milan, Hakan Çalhanoğlu isn’t bought.
Having bought Koulibaly would mean Gasperini would have a crucial CB in the back 3. (Due to the purchase of Koulibaly, Bonucci is never purchased.) Franck Kessié is still brought in on a two-year loan deal with the obligation to buy. Gasperini (just like with Atalanta) targets Robin Gosens (having Gosens means no Ricardo Rodríguez) and also brings Bryan Cristante back to AC Milan on a loan with the option to buy. Gasperini plans on using Bryan Cristante at both CB and CM. (Meaning Mateo Musacchio is also not bought. Also having Ibrahimović, Iličić, and Patrick Cutrone around for the 9 role, André Silva is not needed. Andrea Conti wasn’t in Gasperini plans at Atalanta so I see no reason why he’d target him in Milan.)
**Having only these signings and loans should get Milan out of there upcoming Financial Fair Play problems.
With a much more solid line up and depleting Napoli a little, AC Milan finish in 4th place in the league again. However, this time they qualify for the Champions League.
**If Zlatan had a 2 year contract. (Like with Man United) He’d sign an extension to stay around for the chance for the Champions League title to chase Zlatan. Also to play for a coach and system he believes in.
2018-19
Having expressed his desire to leave Manchester United Matteo Darmian is sought after to add depth in Wing Back positions. Making a return to AC Milan. Fellow EPL rival Angelo Ogbonna also comes back to Italy joining AC Milan after finding success at West Ham United.
AC Milan still target Lucas Paquetá and he’s bought from Flamengo. Begin used both at CF and CM role regularly.
Manuel Locatelli is still sent out on loan to Sassuolo. However, this time around there is no buy option.
**AC Milan go on to have a great year in Serie A, but unfortunately finish 3rd in a tight race for 2nd.
Gasperini leads AC Milan to his 1st Supercoppa Italiana victory! Additionally, this time around Milan beat Lazio in the Semifinals and Atalanta in the Finals. Winning their 2nd Coppa Italia trophy under Gasperini.
(Finishing in 4th last season Milan would replace Inter in the UCL competition)
In the Champions league AC Milan would’ve pushed themselves into the 2nd spot of the group, leaving Tottenham out of the Knockout stage.
AC Milan claw their way to the Final, but ultimately lose to a strong Liverpool team.
2019-20
Manuel Locatelli returns to Milan and goes on to have plenty of chances on the first team.
Thiago Silva once said back when he was sold in 2012 that he would like a move back to AC Milan some day. Having a year left on his contract AC Milan seek Thiago Silva in hopes of paying a little less. PSG receive a decent offer and Thiago Silva is given a good contract, both PSG and Silva accept these offers. Thiago Silva finally makes his long awaited return to Milan!
AC Milan also bring in some younger blood to add even more depth to the back 3 with the purchase of Gianluca Mancini from Atalanta BC. With them outright buying him the offer was more pleasing than waiting for money from AS Roma.
AC Milan still try to purchase Dominik Szoboszlai and Mohamed Simakan in the January winter transfer window. (This time as Milan are in a good position, they choose to join.)
Simakan quickly shows promise taking Matteo Gabbia’s spot on the team.
Szoboszlai also gets chances showing a promising start, but with so much competition at CF and CM is eventually sent out on loan.
Antonio Donnarumma is given an extension to try to convince Gianluigi to stick around longer.
(With Zlatan, Iličeić, and Cutrone around Krzysztof Piątek is never bought. Having had a larger impact and more success Patrick Cutrone is not sold this season and is given more opportunities.)
**With a much stronger Milan squad the race for Serie A Champion would been even tighter this season. This time AC Milan come out on top, winning the title after a 9 year drought!
(Finishing in 3rd last season AC Milan swap places with Atalanta in the UCL.) They finish behind Manchester City in the group, beat Valencia in the Round of 16. AC Milan also beat PSG in the Quarterfinals in a tight match and RB Leipzig in the Semifinals. Heading off to play FC Bayern Munich in the 2020 Finals. Zlatan Ibrahimović knocks in a game winner: finally winning his 1st UEFA Champions League title and AC Milan win their 8th trophy 🏆in team history!
2020-21
Coming off a strong campaign last season AC Milan look to continue their success and strengthen their squad even more.
Georginio Wijnaldum is purchased in the summer transfer window for a good price with only a year left on his contract. Quickly making himself an important starter.
Emerson Palmieri also joins Milan on loan with an option to buy. (Which is used later on in order for him to stay.)
Ciprian Tătărușanu is still bought adding more depth as a solid backup at GK.
Szoboszlai is sent on a year loan to German club Freiburg to help improve his abilities and gain more experience.
Antonio Donnarumma is given an extension to try to convince Gianluigi to stick around longer.
With Simakan around, Matteo Gabbia is also sent out on loan given the chance to improve his game and get playing elsewhere.
Gianluigi Donnarumma seeing more success at Milan: signings an epic new contract extension to stay with AC Milan for the foreseeable future. (Or at least a few more years.)
**Under Gasperini, Daniel Maldini may see more chances. However, he’d be used similar to Paquete at both CF and CM in order to get playing time.
AC Milan still finish in 2nd place in the league, but the race for 1st was much tighter. In the Coppa Italia, Milan beat rivals Inter Milan. However, they end up losing to Juventus in the semifinals.
(Finishing 1st in the League we’ll say they take Juve’s spot in the group stage. Meaning Juve would be in group B, Inter Milan in Group D, & Atalanta in Group F: leaving Lazio in the Europa. *However it’s impossible to say how it would go. Juventus should top or be 2nd in Group B. Inter Milan and Atalanta finish 2nd or 3rd in their groups.)
**Reigning Champs AC Milan top their group in the UCL. Beating FC Porto in Round of 16. With a strong enough team they could beat Chelsea in the Quarterfinals and Real Madrid in the Semifinals. (The winner of the final VS Manchester City is yours to decide!)
2021-22
With Zlatan aging/injury prone and Cutrone not entirely reaching his potential. AC Milan choose to target a much younger and promising striker. Gian Piero Gasperini believes Adam Hložek fits his model forward and requests him. Milan pay what’s needed to get Hložek and he adapts we’ll playing both ST and CF under his system.
(Could this alternate AC Milan win Serie A and/or a Champions League?)
1. What players would you have used?
2. Is there anyone not kept that could be crucial right now? Anyone that should be gone entirely? Or another player Gasperini would’ve probably had?
3. Are the position changes too much of a stretch?
4. What manager if not Gian Piero Gasperini would have worked better in this timeline?
5. Would this formation help AC Milan be successful?
(Just like with my last 2 “What if?”)
I’ll only mention my major alternative moves, changes, and alternate histories. Keep in mind mistakes will still made because no board or manager is perfect. (For example: Pierre Aubameyang, Pirlo and Thiago Silva are still also sold.) Feel free to ask any questions or add input. I’m happy to explain or add to the story.
In this timeline…
2016-17
AC Milan are in search of a manager once more, Vincenzo Montella is more of a fall back manager. Instead Gian Piero Gasperini is offered the job 1st and given a better offer than what Atalanta BC offered him. He graciously accepts and so begins AC Milan’s New Age! Gian Piero Gasperini would begin to implement his 3-4-3 formation and variations.
Not having much of a transfer budget to work with, Milan heavily target free agent Zlatan Ibrahimović who chooses AC Milan over Manchester United, taking on the challenge of returning Milan to its former glory. Also receiving a better deal. (*Alt move* Regardless he’d have a year left in contract with Man U the following year: AC Milan would pay the money necessary to buy him then.)
**Gasperini chooses to keep Stephan El Shaarawy and use him in the CF role of his system.(Although later acquiring better options for the position he still keeps El Shaarawy for depth.)
Mario Pašalić would still come to Milan on loan and would later be purchased.
Gasperini seeing Josip Iličeić’s potential chooses to buy him earlier than he did with Atalanta. (Becoming a key stater at AC Milan over the years.)
**Gian Piero Gasperini leads AC Milan to a 4th place finish. (just as he did with Atalanta) AC Milan however, do find more success in the Coppa Italia beating Juventus in their knockout match. Having taken out this giant AC Milan continue their momentum going on to win the Coppa Italia.
Having a promising start, Gasperini is given another year to lead Milan to the Champions league.
2017-18
This season AC Milan still have a very large budget. **With this being such a pivotal transfer window for success, it’s almost entirely different. (Most transfers each season would be different with Gian Piero Gasperini at the helm. Again I’ll only mention major moves.)
This time AC Milan use the large budget to poach some big Serie A stars, but this time from Napoli. Milan throw big money at Lorenzo Insigne and Kalidou Koulibaly. (Insigne would play the same role Gomez played for Gian Piero Gasperini in real life.)**With Insigne at Milan, Hakan Çalhanoğlu isn’t bought.
Having bought Koulibaly would mean Gasperini would have a crucial CB in the back 3. (Due to the purchase of Koulibaly, Bonucci is never purchased.) Franck Kessié is still brought in on a two-year loan deal with the obligation to buy. Gasperini (just like with Atalanta) targets Robin Gosens (having Gosens means no Ricardo Rodríguez) and also brings Bryan Cristante back to AC Milan on a loan with the option to buy. Gasperini plans on using Bryan Cristante at both CB and CM. (Meaning Mateo Musacchio is also not bought. Also having Ibrahimović, Iličić, and Patrick Cutrone around for the 9 role, André Silva is not needed. Andrea Conti wasn’t in Gasperini plans at Atalanta so I see no reason why he’d target him in Milan.)
**Having only these signings and loans should get Milan out of there upcoming Financial Fair Play problems.
With a much more solid line up and depleting Napoli a little, AC Milan finish in 4th place in the league again. However, this time they qualify for the Champions League.
**If Zlatan had a 2 year contract. (Like with Man United) He’d sign an extension to stay around for the chance for the Champions League title to chase Zlatan. Also to play for a coach and system he believes in.
2018-19
Having expressed his desire to leave Manchester United Matteo Darmian is sought after to add depth in Wing Back positions. Making a return to AC Milan. Fellow EPL rival Angelo Ogbonna also comes back to Italy joining AC Milan after finding success at West Ham United.
AC Milan still target Lucas Paquetá and he’s bought from Flamengo. Begin used both at CF and CM role regularly.
Manuel Locatelli is still sent out on loan to Sassuolo. However, this time around there is no buy option.
**AC Milan go on to have a great year in Serie A, but unfortunately finish 3rd in a tight race for 2nd.
Gasperini leads AC Milan to his 1st Supercoppa Italiana victory! Additionally, this time around Milan beat Lazio in the Semifinals and Atalanta in the Finals. Winning their 2nd Coppa Italia trophy under Gasperini.
(Finishing in 4th last season Milan would replace Inter in the UCL competition)
In the Champions league AC Milan would’ve pushed themselves into the 2nd spot of the group, leaving Tottenham out of the Knockout stage.
AC Milan claw their way to the Final, but ultimately lose to a strong Liverpool team.
2019-20
Manuel Locatelli returns to Milan and goes on to have plenty of chances on the first team.
Thiago Silva once said back when he was sold in 2012 that he would like a move back to AC Milan some day. Having a year left on his contract AC Milan seek Thiago Silva in hopes of paying a little less. PSG receive a decent offer and Thiago Silva is given a good contract, both PSG and Silva accept these offers. Thiago Silva finally makes his long awaited return to Milan!
AC Milan also bring in some younger blood to add even more depth to the back 3 with the purchase of Gianluca Mancini from Atalanta BC. With them outright buying him the offer was more pleasing than waiting for money from AS Roma.
AC Milan still try to purchase Dominik Szoboszlai and Mohamed Simakan in the January winter transfer window. (This time as Milan are in a good position, they choose to join.)
Simakan quickly shows promise taking Matteo Gabbia’s spot on the team.
Szoboszlai also gets chances showing a promising start, but with so much competition at CF and CM is eventually sent out on loan.
Antonio Donnarumma is given an extension to try to convince Gianluigi to stick around longer.
(With Zlatan, Iličeić, and Cutrone around Krzysztof Piątek is never bought. Having had a larger impact and more success Patrick Cutrone is not sold this season and is given more opportunities.)
**With a much stronger Milan squad the race for Serie A Champion would been even tighter this season. This time AC Milan come out on top, winning the title after a 9 year drought!
(Finishing in 3rd last season AC Milan swap places with Atalanta in the UCL.) They finish behind Manchester City in the group, beat Valencia in the Round of 16. AC Milan also beat PSG in the Quarterfinals in a tight match and RB Leipzig in the Semifinals. Heading off to play FC Bayern Munich in the 2020 Finals. Zlatan Ibrahimović knocks in a game winner: finally winning his 1st UEFA Champions League title and AC Milan win their 8th trophy 🏆in team history!
2020-21
Coming off a strong campaign last season AC Milan look to continue their success and strengthen their squad even more.
Georginio Wijnaldum is purchased in the summer transfer window for a good price with only a year left on his contract. Quickly making himself an important starter.
Emerson Palmieri also joins Milan on loan with an option to buy. (Which is used later on in order for him to stay.)
Ciprian Tătărușanu is still bought adding more depth as a solid backup at GK.
Szoboszlai is sent on a year loan to German club Freiburg to help improve his abilities and gain more experience.
Antonio Donnarumma is given an extension to try to convince Gianluigi to stick around longer.
With Simakan around, Matteo Gabbia is also sent out on loan given the chance to improve his game and get playing elsewhere.
Gianluigi Donnarumma seeing more success at Milan: signings an epic new contract extension to stay with AC Milan for the foreseeable future. (Or at least a few more years.)
**Under Gasperini, Daniel Maldini may see more chances. However, he’d be used similar to Paquete at both CF and CM in order to get playing time.
AC Milan still finish in 2nd place in the league, but the race for 1st was much tighter. In the Coppa Italia, Milan beat rivals Inter Milan. However, they end up losing to Juventus in the semifinals.
(Finishing 1st in the League we’ll say they take Juve’s spot in the group stage. Meaning Juve would be in group B, Inter Milan in Group D, & Atalanta in Group F: leaving Lazio in the Europa. *However it’s impossible to say how it would go. Juventus should top or be 2nd in Group B. Inter Milan and Atalanta finish 2nd or 3rd in their groups.)
**Reigning Champs AC Milan top their group in the UCL. Beating FC Porto in Round of 16. With a strong enough team they could beat Chelsea in the Quarterfinals and Real Madrid in the Semifinals. (The winner of the final VS Manchester City is yours to decide!)
2021-22
With Zlatan aging/injury prone and Cutrone not entirely reaching his potential. AC Milan choose to target a much younger and promising striker. Gian Piero Gasperini believes Adam Hložek fits his model forward and requests him. Milan pay what’s needed to get Hložek and he adapts we’ll playing both ST and CF under his system.
(Could this alternate AC Milan win Serie A and/or a Champions League?)
1. What players would you have used?
2. Is there anyone not kept that could be crucial right now? Anyone that should be gone entirely? Or another player Gasperini would’ve probably had?
3. Are the position changes too much of a stretch?
4. What manager if not Gian Piero Gasperini would have worked better in this timeline?
5. Would this formation help AC Milan be successful?
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