The one that got away...

Where are they now? Gennaro Gattuso’s 11 signings as AC Milan manager

Gennaro Gattuso was a legendary player for AC Milan, but his stint as the club’s manager didn’t quite go as fans would’ve hoped and his signings from his tenure reflect that.

We’ll cut Gennaro some slack here, not just because we’re terrified of him coming to England and kicking our heads in, but also because his spell in charge from 2017 to 2019 came in the midst of one of Milan’s darkest hours, while they swapped dodgy owners for fun and rotted in Serie A’s mid-table without a hope in the world.

He did his best, but succumbed to the same, inevitable fate as others around him. We’ve looked back at the 11 signings made while he was in the hot seat.

Pepe Reina

His first signing as Milan manager, Reina joined on a free transfer from Napoli and served as experienced backup to Gianluigi Donnarumma, but did play in the Europa League in 2018-19 as the Rossoneri were dumped out in the group stages.

Reina left on loan to Aston Villa in 2020 – weird – and joined Lazio that summer. He’s still playing right now at the ripe old age of 100 (41) for Villarreal and has made 11 appearances so far in 2023-24.

Ivan Strinic

2018-19 would prove to be Strinic’s final season as a professional footballer, spending one season with Milan after signing on a free transfer from Sampdoria.

His campaign was scuppered by a heart condition detected after the World Cup which halted his career, but he returned in January 2019, before retiring that August, hanging up his boots without actually ever playing a competitive game for the club.

Strinic has lived a rather quiet life since retiring and not much has been said about what he’s up to currently.

Alen Halilovic

After being stung by taking a punt on Bojan earlier in the 2010s and then being unable to guide Hachim Mastour on the right path, of course Milan deemed it worthwhile to take a punt on yet another ‘wonderkid’ who had been through the wringer in Halilovic, signing on a free transfer from Hamburg.

He was out on loan by 2019 and left for Birmingham City in 2020. After a brief spell in England’s second tier, the midfielder – who is still only 27 – is now playing in the Eredivisie with Fortuna Sittard.

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Mattia Caldara

After a nightmare move saw Leonardo Bonucci spend one horrific season in Milan in the 2017-18 season, he moved back to Juventus in the summer, with them selling Caldara to Milan for €35million in a similar deal.

The Italian defender struggled to fit into a back four system and was ravaged by injuries in his first season, returning in February 2019 only to rupture his ACL that April. By the time he’d returned, Gattuso had gone and Stefano Pioli had begun to sculpt Milan into his own vision.

Caldara was shipped out on loan, but is still on the books with Milan now and looked set to play a part in 2023-24 after failing to agree a transfer away.

He returned from an injury in February 2024, but is not included in the club’s Europa League squad and is likely to finally leave this summer – for nothing.

Gonzalo Higuain

Another poor signing from Juventus, Milan’s strategy at the time appeared to be to try and sign the champions’ cast-offs.

Milan paid an €18million loan fee to sign Higuain for the 2018-19 season; that loan had been terminated by January and Higuain was instead loaned to Chelsea, where he also flopped.

He retired in 2022 after two years with Inter Miami.

Alexandro Cavagnera

Belgian midfielder Cavagnera was loaned out immediately after signing for the club, only to be released from his contract in September 2019.

Now 25, he currently plays for Wiltz in Luxembourg. Another terrible signing, but at least it didn’t cost them much money this time.

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Samu Castillejo

Signed in the summer of 2018 from Villarreal in a deal that saw Carlos Bacca head the other way, Castillejo enjoyed two seasons of regular football on the right flank for Milan, but very quickly lost his place after Pioli became the club’s permanent manager and put them on an upward trajectory again.

Ultimately, it became obvious that he wasn’t of the required standard and he was eventually sold to Valencia in 2022 after failing to agree a move in the summer of 2021.

He’s now back in Serie A with Sassuolo, however, joining them on loan in 2023.

Tiemoue Bakayoko

After signing for Chelsea with all the promise in the world but being deemed not good enough after one season, the Rosssoneri took a punt on Bakayoko, who picked up after a slow start, but rejoined Monaco on loan the following season.

He returned to Milan on a two-year loan in 2021, playing 14 Serie A games as Milan lifted the Scudetto in 2021-22, but is now back in Ligue 1 with Lorient. Chelsea's Eden Hazard celebrates after scoring his side's fourth goal during the Europa League Final soccer match between Arsenal and Chelsea at the Olympic stadium in Baku, Azerbaijan, Wednesday, May 29, 2019.

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Diego Laxalt

Known for his cornrows and not his abilities, Laxalt was deemed surplus to requirements just one season after joining Milan for an initial €14million.

The left-back was loaned to Torino and later Celtic, before eventually leaving the club permanently in 2021 to sign for Dynamo Moscow.

Despite the ongoing Russian invasion of Ukraine, Laxalt – now 31 – has remained with Dynamo Moscow and signed a contract extension through to 2026 in October 2023, having found a vein of form once again.

Lucas Paqueta

After years of truly terrible business, Milan thought they had the one when they paid €35million to sign Paqueta, beating other European clubs to his signature.

The transfer was confirmed in January 2019 and Paqueta featured regularly, but struggled to show his best stuff and was caught up in the chaos that was the Rossoneri at the time.

In need of a fresh start, Milan cut their losses in September 2020 and sold the Brazilian to Lyon, where he found his feet again and began to fulfil his potential.

Now 25, it’s taken Paqueta a little longer than expected after a false start, but he’s comfortably one of the best midfielders in the Premier League with West Ham and is widely tipped to make a big-money move imminently, having almost joined Manchester City in 2023.

Right player, wrong time. The one that got away.

Krzysztof Piatek

After a lightning-fast start for Genoa in the 2018-19 campaign where he became the first striker since none other than Andriy Shevchenko to score five goals in his first four Serie A appearances, Milan pulled the trigger on signing Piatek in January 2019.

They parted with a reported €35million after Genoa had only paid €4million for him mere months earlier, needing to do so to replace the swiftly departed Higuain.

He made a brilliant and prolific start to life in red and black, bagging a brace against Napoli in the Coppa Italia, but slowed down considerably after Gattuso’s departure, failing to click under Marco Giampaolo and losing his place under Pioli. A year after joining, he was sold to Hertha BSC.

Now 28, Piatek finds himself in an inevitable spell in the Turkish Super Lig, leading the line for Istanbul Basaksehir. He scored his first hat-trick for the club at the beginning of 2024.