AC Milan have had a nightmare January but that's good news for Spurs

Paolo Maldini wasted £44m on flops, stars are failing to deliver and boss Stefano Pioli keeps getting it WRONG… AC Milan endured a nightmare January – but that’s good news for Spurs as their Champions League showdown beckons

  • AC Milan suffered a humiliating 5-2 Serie A loss at home to Sassuolo last Sunday 
  • Charles De Ketelaere has failed to deliver on the promise he showed last season
  • The Rossoneri are in the middle of a goalkeeper crisis with Mike Maignan injured 

AC Milan have had a nightmare start to 2023, dropping 10 points already, highlighting the several weak points in the team. 

The club’s period in the sun seems to be over with a number of players clearly bereft of form and struggling to perform to their own previous high standards.

Theo Hernandez is unrecognisable, Olivier Giroud is on his last legs, but the biggest concern is the psychological condition of the team.

Against Sassuolo, Pioli’s side enjoyed 61 per cent of the ball but were stagnant in possession and conceded five goals out of six shots on goal – an embarrassing record proving the team’s defensive fragilities. The team appear dead on their feet. 

Stefano Pioli and his technical staff are similarly culpable for the team’s demise, having allowed the free transfers of Franck Kessie and Hakan Calhanoglu in the last two years without signing replacements. 

AC Milan came unstuck in a 5-2 defeat to Sassuolo amid a nightmare start to the year

The Rossoneri’s physical preparation is also under scrutiny, after a dramatic increase in injuries over the last three years.

Pioli’s fear is shown by his actions on the touchline and his ill-devised decision-making in the vain hope of reviving both himself and his team. 

The decision to leave Rafael Leao on the bench for 45 minutes perfectly encapsulates this confusion; dropping his star player only for it to blow up in his face.

There are a litany of issues at the San Siro, none of which look remotely close to being solved in the immediate future. 


It is difficult to pin the failings of an entire backroom team on one culprit. 

Yet a more in-depth analysis highlights that a large part of Milan’s problems arise from poor decisions in the transfer market by technical director Paolo Maldini. 

None of the players brought in over the summer come close to the required quality for Serie A level. 

New Italian club owners are growing increasingly concerned with Milan’s recent mistakes in the market, claiming that they have in fact weakened rather than strengthened the structure of the team. 

Technical director Paolo Maldini has been wasteful in charge of the club’s transfer policy

This explains Gazzetta dello Sport’s recent reports that tensions within the club are rising. Maldini and Ricky Massara are now in a very delicate position, and risk the finger being pointed at them if they failed to qualify for next season’s Champions League.

Maldini and Massara wasted £44million (€50million) during the summer transfer market on six players who have all fallen some way short of expectation. 

Yacine Adli, Tommaso Pobega, Aster Vranckx and Malick Thiaw have shown nothing to disprove they are the flops the Rossoneri fans already believe them to be.

But the club’s worst two signings so far have been their most expensive. The gambles made on Charles De Ketelaere and Divock Origi – for two very different reasons – weigh heavily against Maldini. 

Neither player has come close to the expectations they promised, and both have struggled to get to grips with Pioli’s system. 

AC Milan splashed around £30.7m on the former Club Brugge starlet, and have been repaid with frequently below-par performances from the Belgian, while the high salary afforded to the ex-Liverpool star has not been reflected in his goal tally. 

Divock Origi’s goal return in Serie A has not vindicated the decision to make him one of the club’s top earners


In Italy, they say that choosing the right goalkeeper is the most important part of building a successful team. Ciprian Tatarusanu is almost non-existent in between the sticks, picking the ball out of the net on a seemingly constant basis. 

Mike Maignan’s prolonged absence has raised concerns over his fitness for both Pioli and Maldini. Perhaps more was expected from the veteran Romanian but he had already fallen to No 3 in the pecking order behind Maignan and Antonio Mirante before the season had started. 

The French No 1’s injury and the age of deputy Mirante, 39, handed Tatarusanu the opportunity, but his inconsistency has seen the good punctuated with the sloppy. 

Tatarusanu was clumsy in conceding Davide Frattesi’s second for the visitors against Sassuolo, completely mistimed Domenico Berardi’s header for their third, and was cumbersome in getting down to his left for the fifth.

Every decision the Romanian made was wrong, and his defence was left unsure every time Sassuolo had a shot at goal. 

Ciprian Tatarusanu was clumsy and cumbersome in goal for the Rossoneri against Sassuolo


Theo Hernandez has been a shadow of his former self after France’s failed World Cup defence, and is unable to bomb up and down the left flank with the regularity he had previously shown. 

He was completely dominated by Sassuolo, which forced him to defend deep in his own half, rather than influence the game in midfield. He was unable to help the team, and was left watching on as Milan sank without a trace. 

The World Cup winner was given a torrid day by Berardi, who repeatedly caused problems for the Milan back four, and is sure to feature in Hernandez’s nightmares for some time. 

Hernandez perhaps needs to be rested, but Milan’s need of their vice-captain is heightened by the absence of any capable replacement. 

Hernandez returned to the club at the end of the World Cup not only exhausted, but also dejected and distraught following Les Bleus’ heartbreaking defeat to Argentina. 

Theo Hernandez returned to Milan exhausted after a World Cup run that ended in heartbreak


Charles De Ketelaere would struggle to make the second team at AC Milan

It could have been the match to kick start De Ketelaere’s AC Milan career, but instead ended in nightmare, with his own fans booing his every touch of the ball. 

Fans at the San Siro do not readily forgive even the slightest technical errors, and the young Belgian midfielder seemed to take those jeers to heart more than any pundits criticism he has received in Italy. 

The former Brugge star is very shy, and it would seem is unable to deliver on the potential his highly-vaunted arrival promised expectant fans. 

The Belgian doesn’t look to have the necessary grit to thrive in a very arduous, physical Serie A, and perhaps another 12 months on loan in Belgium might have been more beneficial in strengthening his character. 

De Ketelaere seems incapable of adapting to the tactical nuances of Italian football and after yet another poor display against Sassuolo, the midfielder is officially in crisis. Rossoneri fans need to show greater patience, but right now the youngster looks all at sea for both club and country. 

De Ketelaere is not delivering on his promise, and looks full of fear at the slightest hint of a challenge on the ball, frequently caught in possession and powerless to win it back. 

The Belgian youngster is fearful in possession and appears powerless to regain the ball


Antonio Conte’s Tottenham have had their own issues at times this campaign

While AC Milan continue to implode, former Inter boss Antonio Conte will surely only rub his hands with glee at the prospect of next month’s Champions League meeting. 

Spurs themselves have had a far from routine season, but with the north London side themselves bereft of confidence, a clash with an equally struggling side could be just what his team needs. 

Spurs have shown signs of an all-too-familiar collapse of late, having dropped nine points in the new year including a defeat to bitter rivals Arsenal, and are currently outside the Champions League spots in the Premier League. 

They may be in the hat for the fifth round of the FA Cup, but a strong run in Europe’s top competition could be the lift that fans need to quell any bubbling tension beneath the surface targeted at Conte.

Son Heung-min may have scored a stunner against Preston in the FA Cup, but it has been hard going for the usually dependable South Korean, leaving Harry Kane to pick up much of the slack in his absence. 

Son will surely be grinning to himself in gleeful anticipation watching back the highlights of Milan’s calamitous workshop on how not to defend against Sassuolo. There is an argument this tie is the dream draw for a recovering Spurs side.

Aside from avoiding the obvious big-hitters, Tottenham have evaded the clutches of a Club Brugge side that shocked Atletico Madrid, and the Bundesliga duo of Dortmund and RB Leipzig that have caused several top sides issues in recent years. 

Both sides have seemed shadows of the sides that ended 2021-22 so well this campaign, and both are in dire need of a crowd-pleasing Champions League run, but the problems at Tottenham are left trailing in the wake of the implosion occurring at the Rossoneri.  

Like Milan, Spurs are in dire need of a crowd-pleasing Champions League run to quieten the growing discontent

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