As Paolo Maldini lifted the Champions League trophy in 2007, jubilation filled the black and red half of Athens’ Olympic Stadium, as the streets of Milan partied to celebrate their club’s seventh European Cup and their second in just four years. The Rossoneri were at the pinnacle of football, but as they came to realise; when you’re on top of the world, you have a long way to fall.
That side boasted aging stars and club stalwarts who helped Milan stay relevant in a league which was ultimately steamrolled by city rivals Inter from 2005-2010, as Silvio Berlusconi – their esteemed owner since 1986 – was also coming to the end of his tenure amid an inability to compete with the riches of modern football.
Their denouement was sudden and drastic; four years after winning Serie A for the final time, Milan had tumbled into the bottom half of the top flight for the first time 1998 – culminating in a messy saga of failed sales and dodgy dealings, as Milan continued to flounder on the pitch.
But as Li Yonghong joined in 2017, they splashed the cash in a desperate attempt to fast track the Rossoneri back into title and European contention – but their lack of strategy prevented any of that, as we look to dissect their summer spreading spree.
Antonio Donnarumma – £880,000 – Asteras Tripoli
For all the deals made during the 17/18 summer window, perhaps Milan’s finest was tying down wonderkid goalkeeper Gianluigi Donnarumma to a new four-year contract after the teenage sensation decided he would be leaving San Siro.
But in order to do that, a verbal agreement was decided that Gianluigi’s older brother Antonio would re-sign for the Italian giants – five years after being sold to Genoa for £1.5m.
By 2017, though, Gianluigi had already long surpassed his brother’s talent and achievements – managing 72 first-team games for Milan by the time Antonio had racked up 94 senior career appearances at the age of 27.
While Milan denied he was brought in solely to make his brother happy, there seemed like little other rhyme or reason for why they would fish a goalkeeper out of the Greek first division to play as second, third or even fourth fiddle.
He did play three games for his boyhood club during his second spell; wins against SPAL and Ludogorets, but most memorable was the 1-0 Coppa Italia win over Inter – a result which briefly catapulted him to cult hero status amongst Milanistas.
Donnarumma departed for free last summer (along with his younger brother), with the distinction of holding a 100% clean sheet record during his fleeting San Siro career.
Fabio Borini – £450,000 loan fee + £4.95m – Sunderland
If somebody had told Fabio Borini when he was plying his trade in the Bologna youth ranks that he would go on to play for Chelsea, Parma, Roma, Liverpool and AC Milan, then he could have been forgiven for believing that he would go on to become one of the best strikers in Europe both at home and abroad. But it hasn’t quite worked out that way.
Following lacklustre spells in England with Liverpool and then Sunderland, the latter were relegated and Borini was offered a route out with a one-year loan to Milan with an obligation to buy at the end of it – we’re sure he couldn’t believe his luck.
But in fairness to Borini, he pleasantly surprised large parts of the Milan faithful – impressing with his work rate, attitude and willingness to fill in all over the pitch, from either flank, up front and even at full-back.
He departed after two seasons to join Hellas Verona on a free transfer, leaving Milan with 14 goal contributions from 75 games. Hardly a stellar total, but he certainly ranks more favourably than some of the more expensive mistakes made that summer.
Nikola Kalinić – £4.5m loan fee + £20.25m – Fiorentina
Following two fruitful years at Fiorentina, Nikola Kalinić was again catching the eye of Europe’s biggest clubs – some six years after a poor spell at Blackburn appeared to end any ambitions of making it in one of the major leagues.
He had been involved in 36 goals in 69 Serie A games for La Viola and Milan decided they wanted a piece of what the Croat had to offer, bringing him in initially on a one-year loan.
Kalinić might have been 29 by the time he moved, but he had improved during both his seasons there and also managed to underperform his xG by almost six goals all told – suggesting there was still more to come from the former Rovers hitman.
If Milan could have gotten the striker who had scored goals aplenty in Florence, then the £25m fee spread over two seasons might not have been too bad – but that didn’t really happen.
He spent part of the season behind Patrick Cutrone (who bagged 18 goals in 17/18), while managing to hit just two Serie A goals between matchday 22 and 38 himself. The Rossoneri paid the money come the summer, but Kalinić was quickly on the move again – joining Atlético Madrid for £13m where he also failed to shine.
Some signings just don’t quite work out, and the fact he only cost them a net of just £6m per season means that Milan somewhat got away with this one.
Franck Kessié – £7.2m loan fee + £21.6m – Atalanta
Only three players from AC Milan’s 23-man squad for 2017/18 remain at the club; Alessio Romangnoli, Davide Calabria and Franck Kessié, with the Ivorian the only of these 11 signings still standing at San Siro.
Those are remarkable numbers, and perhaps show best how far the club has come under the stewardship of Ivan Gazidis, Paolo Maldini and Geoffrey Moncada, as well as how standards have risen between the ‘old’ and ‘new’ Milan.
In that time, Kessié has featured in at least 34 Serie A matches in each season – totalling more than 215 games in Red and Black so far, playing a vital role as Milan have gone from Europa League contenders to bonafide title challenges in the years since.
However, a player who arrived with much promise at the start of this project looks set to depart just as it could reach its conclusion. The Ivorian’s contract runs out at season’s end which has kept most of the big boys on high alert for the 25-year-old, with Barcelona seemingly the most likely destination for one of Stefano Pioli’s star men.
While Kessié originally started slowly, nobody can doubt his importance to Milan in certainly the last few seasons – it’s just a shame that one of the few success stories will fail to garner any resale value for a player just hitting his prime years.
Ricardo Rodríguez – £13.5m – Wolfsburg
Having developed into one of the top left-backs in Europe during his time in Lower Saxony, Ricardo Rodríguez departed Wolfsburg to join Milan for a cut-price fee of £13.5m – slightly lower than the deal the Swiss international originally agreed with City rivals Inter six months prior, only for the move to fall through.
Rodríguez was steady if not remarkable for the Rossoneri, moving away from the buccaneering, goal-contributing machine we saw in the Buli, and morphing into a more defensive option on the left side of defence.
Of course, this wasn’t helped by losing his penalty-taking duties and playing a different style of football, but the 50 goal involvements he managed for Die Wölfe dwarfed the relatively meagre nine he produced during his 93 Milan appearances.
He was duly replaced by Theo Hernandez and loaned out to PSV, before a permanent £1.75m switch to Torino in 2020 brought to an end an overall underwhelming three-year spell at Milan.
Mateo Musacchio – £16.2m – Villarreal
After a rollercoaster time at Villarreal – which included two stints in the Segunda as well as a Champions League campaign – Mateo Musacchio moved onto pastures new, joining Milan in a £16.2m deal to provide cover or a partner for Alessio Romagnoli and the newly acquired Leonardo Bonucci.
He managed 15 appearances in his debut campaign, often used as deputy for one of Milan’s Italian centre-backs or the left option in a back three – earning praise for his physicality and agility in the backline.
This meant that, when Bonucci returned to Juventus at the season’s end, Musacchio played 29 games in 18/19 as Milan once again finished in the European places.
While they kept faith with their South American defender once more come 2019/20, the former River Plate man was duly muscled out by new arrival Simon Kjær – one of the catalysts of Milan’s assault on the top of Serie A – and soon after, Musacchio’s time at San Siro took a turn for the worst as keyhole ankle surgery kept him out for ten months.
Upon his return, he managed just half-an-hour of football for Stefano Pioli’s men before departing for Lazio in January 2021 on a free transfer. Similarly to Rodríguez, Musacchio wasn’t the worst player to step out onto the San Siro turf, but at a £16m loss from just 75 appearances, he was hardly value for money.
Lucas Biglia – £17.7m – Lazio
At £17.7m, Lucas Biglia was then ranked as the 2nd most expensive signing in football history (and still resides in the top 15 now) for players 31 and over – with only Gabriel Batistuta costing more in that age range when he moved to Roma in 2000.
That market has little resale value, and one often shopped with a view to signing veteran players for free or nominal fees, rather than the extortionate amount Milan spent on the Argentine central midfielder.
That’s not to say Biglia was a bad player; he’d been the cornerstone of a successful Lazio side which qualified for the Champions League and reached two Coppa Italia Finals.
But when you’re spending that sort of money, you ideally need to be shopping in an elite market for a player with a solid injury record – but the former Anderlecht man had been perennially stalled by niggling setbacks, and the story was similar at San Siro.
He wasn’t alone in being the only new arrival off the pace at the beginning of the season, but where the likes of Rodríguez and Musacchio settled into a somewhat comfortable rhythm, Biglia struggled and missed a total of 43 games in just three seasons for the Italian Giants, while his powers were visibly waning into an inconsistent mess on the field.
Like many before him, Biglia eventually left for free – bemoaning the lack of consistency at Milan upon his departure, namely the managerial and ownership issues which threatened to derail the club’s progress.
The Argentine midfielder now plies his trade at Turkish side Fatih Karagümrük alongside fellow 17/18 arrival Fabio Borini with the 36-year-old’s contract set to expire in June, but he offers as a lesson which resulted in Milan generally shopping in a younger market or exclusively with risk-free elder statesmen (Olivier Giroud and Zlatan Ibrahimović, for example).
Hakan Çalhanoğlu – £21m – Bayer Leverkusen
While Biglia was the quintessential example of one of the many summer arrivals who struggled to get going in the Fashion Capital, Turkish midfielder Hakan Çalhanoğlu was the antithesis of that – and perhaps represents the best piece of business that Milan did during the off-season.
In that debut campaign, the former Hamburg man was involved in 22 goals in all competitions – placing him top of the Milan assists charts with 14 and second in scoring ranks with eight.
The numbers were never really an issue for Çalhanoğlu – but his all-round game lacked consistency, though he would argue his positioning did little to help that.
Despite lacking blistering pace and operating better in the space a central position can provide, Çalhanoğlu was often deployed on the wing – most notably under Gennaro Gattuso.
Once Milan returned from the enforced Covid break under relatively new man Pioli, he played more football in the number ten role and contributed to 28 goals in 45 Serie A games – the same number he managed from the remaining 91 games in Black and Red. But, crucially, his performances and consistency also received a shot in the arm.
The theme continued; Çalhanoğlu moved on upon the expiry of his contract in the summer of 2021 – choosing the controversial route of moving to city rivals Inter on a reported salary of €5m-per-year.
While many don’t believe the powers that be will lose much sleep over him if they bring the Scudetto home this year, it’s still a shame (much like Franck Kessié) to see a rare 17/18 success story go the same way as so many others.
Andrea Conti – £21.6m + Matteo Pessina – Atalanta
For a time, there was a theory that many players who have succeeded at Atalanta over the past five years have struggled once departing La Dea, as the Gian Piero Gasperini system has allowed them to flourish to such levels.
While that is somewhat outdated now, there are clear indications of where that was mostly the case – with Andrea Conti one of those to suffer that fate.
Having arrived from Bergamo fresh off the back of eight goals and five assists from 33 Serie A games, Milan fans were rightfully excited to bring in one of Italy’s rising stars.
However, Conti suffered a debilitating cruciate ligament injury which sidelined him for practically the entirety of his debut season, before knee surgery pushed his recovery back even further.
Once on the pitch, it was clear Conti initially struggled with the transition from a right midfielder/wing-back to a full-back in a flat back four, before settling into the team during 2019/20. But, further injuries cost him his place to the likes of Davide Calabria and Diogo Dalot who retained their starting berths once he returned.
He departed for Parma on loan in January 2021 before bidding goodbye to the San Siro a year later – heading south to join Sampdoria for, you guessed it, absolutely zilch.
André Silva – £34.2m – FC Porto
To quote Gary Neville, this was the no-brainer. This was the banker. This was the one that couldn’t fail. This was the one that’s never failed.
Okay, maybe that last point was a stretch too far, but Portuguese football has proved relatively fertile ground for big money forwards to come and perform in European football – from Raúl Jiménez and Radamel Falcao to Luka Jović and João Felix and so many more.
The Primeira has produced some goal machines who have widely reproduced their goal scoring over in mainland Europe – but André Silva wasn’t one of those at San Siro.
While he went great guns in Europe (netting six from ten Europa league matches), he struggled domestically and took until March 11th to score his first Serie A goal, following his maiden strike with another seven days later against Chievo Verona. But the river ran dry once more, and the big front man failed to find the net again for Milan that season.
A combination of pressure to live up to such a big price, a poor start and a system which didn’t suit his needs resulted in Silva moving to Sevilla on loan and then Frankfurt – joining the latter for a mere £2.7m in 2020 before going on to score goals aplenty for Adi Hütter’s side.
To make matters worse, the Germans then sold him on for ten times that amount just a year later to RB Leipzig, where goals have once again followed. This is perhaps the purest example of Milan’s 17/18 recruitment targeting a good, young player, but not having the facilities for them to blossom – it was simply wrong player, wrong time.
Leonardo Bonucci – £37.8m – Juventus
Last, but most definitely not least, was the statement signing, the signal of intent, the flagship move, as Sid Phillips from Toy Story would say, ‘the big one.’
Leonardo Bonucci was a seven-time winner of Serie A, a six-time domestic cup lifter, twice a Champions League Finalist and had been an integral cog at the heart of Italian football’s most dominant ever side – and he was arriving at San Siro as the symbolic fog horn, to the city’s sleeping giant.
By now, we know the story; Bonucci started somewhat slowly and, despite being named as Milan’s captain, struggled with the ever-changing system of Vincenzo Montella.
As things changed, though, Bonucci struck up a solid partnership with Romagnoli and Milan lost just twice and conceded only 16 goals from the Italian’s final 19 games. But as Milan finished 6th, Juventus claimed yet another Scudetto, and Bonucci soon had his heart set on a return to The Old Lady.
He moved to the Allianz a year later effectively in a swap deal with Mattia Caldara, as well as the loan arrival of Gonzalo Higuaín for around £9.5m – but both of those moves also ended in disaster.
Caldara is still on the books but is on his second loan move away from the club and has mustered just 155 minutes for Mlian, and while Higuaín’s goal return was acceptable, he lasted just four months before departing for Chelsea in the January window.
The idea of Bonucci wasn’t terrible in principle; a trophy-guzzling, commanding, leader of a centre-back who would have had the ability to morph the entire club and drag Milan kicking and screaming into a new era – but none of the other dominoes really fell into place.
While he was the most expensive 30+-year-old in the history of football (and is still 4th now), unlike Biglia, they had a chance to sell him for a small loss – but they even managed to mess that up.
Overall the summer was, to say the least, a complete disaster for Milan’s new regime. Eleven players joined the club, but come the end of the 2021/22 campaign, none will remain and just three of them left for a fee which wasn’t off-set by another arrival, to the tune of just £17.45m.
Leonardo Bonucci wasn’t a poor player for Milan, but the deal which saw him exit San Siro certainly was, while injuries hampered three of the four in the disastrous column and the two lone successes will/have left for nothing.
The spending eventually drove Li out of the club and now, under new ownership and model, Milan are fighting again while picking up countless transfer market gems all the while.
By: James Pendleton / @Jpends_
Featured Image: @GabFoligno / Emilio Andreoli / Getty Images