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AC Milan’s worst signings ever

Rivaldo ATA-MIL

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

AC Milan has a wonderful story filled with many records and trophies. Especially in the years when Silvio Berlusconi was president of the club but not only. Many European and domestic titles won and above all many stars in the team.

Legendary players have in fact dressed the Rossoneri jersey over the years. But there was no lack of flops and disappointments. Here are the seven worst signings ever made by AC Milan, all during the Berlusconi era.

Starting from Winston Bogarde, arriving in Rossonero from Ajax for a single season (1997-1998) without leaving a trace. After only three appearances he was dispatched to Barcelona.

The Netherlands international at the time was part of Ajax’s Champions League-winning squad in 1995, alongside greats such as Van der Sar, Frank Rijkaard, Frank de Boer and Clarence Seedorf. After two years at Barcelona he would later transfer to Chelsea where he made only 9 appearances in four seasons and is regarded as one of the worst signings in Premier League history.

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Patrick Kluivert – CF

Along with Bogarde came another Dutch player: Patrick Kluivert. At the time he was considered one of the most promising strikers in Europe but he failed to shine at AC Milan.

His career at the San Siro started in spectacular fashion after scoring a sensational goal in the Luigi Berlusconi trophy against Juventus. The promising youngster would close the season with only six goals in 27 Serie A appearances.

It was a very disappointing season not only for Kluivert on personal level but for the entire team. Though a star studded squad, AC Milan finished the season in 10-th place in the league. There were simply no conditions for Kluivert to showcase his true qualities.

Patrick Kluivert

The Dutch star moved to Barcelona at the end of the season where he found a completely different luck. Still the Rossoneri got a nice profit from his sale, the only notable consolation from that season. 

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Rivaldo – SS

In this special list the Brazilian legend Rivaldo has also been included. In contrast to the above mentioned players the Brazilian ball wizard took the opposite path, he joined AC Milan after a successful career at Barcelona.

Regarded as one of the greatest Brazilian footballers of all time and one best players of the 2002 World Cup winning Brazilian generation Rivaldo seemed like a signing of guaranteed return. Instead he spent more time on the bench than on the pitch.

In his two seasons at San Siro Rivaldo made only 22 appearances finding the back of the and on 5 occasions. The Brazilian’s best days had long passed but he was still part of the 2003 Champions League winning team.

Rivaldo 

He returned to Brazil for a short lived two months adventure at Cruzerio. Since then he changed teams on a regular basis and continued to play until the age of 43. In the last days of his football career the legendary striker together with his son Rivaldinho scored in the same Brazilian Serie B match for Mogi Mirim.

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Christian Vieri – CF

Christian Vieri achieved legend status at the city rivals of Inter. Hugely successful years for Bobo but only on personal level because his only trophy with Inter would be the Coppa Italia in 2005.

In the same year he terminated his contract with Inter and jumped on the other side. The Italian striker was out of shape in his only season for the Rossoneri. Vieri made 8 outings and scored his for only goal Milan in a 3–1 win against Empoli.

Christian Vieri was a great disappointment but considering his age not much was expected from him. Certainly much better at Inter.

Christian Vieri (© AP Photo/Alberto Pellaschiar)

In January he moved on a free transfer to Monaco. At the end of the season Andriy Shevchenko also left the club.


While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Ricardo Oliveira – CF

The name of Ricardo Oliveira certainly ranks high in this least. The Brazilian striker enjoyed a great spell in Spain at Real Betis and was chosen by Adriano Galliani to replace Andriy Shevchenko.

AC Milan signed Oliveira for a reported fee of 17.5 million euros plus Johann Vogel. He debuted with a goal against Lazio but the remaining of the season was a disaster. He scored a total of 3 goals in his only year at San Siro. 

Unfortunately his performances were influenced by kidnapping of his sister with Oliveira later admitting that he was under the stress and unable to play. It was however a great season for AC Milan who won their seventh Champions League trophy against Liverpool.

Ricardo Oliveira

AC Milan sold him back to Spain at Real Zaragoza for 10 million euros. At the age of 38 Ricardo Oliveira is still playing in his homeland.

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Javi Moreno – CF

In the early 2000’s Javi Moreno was making a name for himself in Spain with Alaves. His performances caught the eye of the Serie A giants who signed him for almost 20 million euros, one of the highest fees AC Milan had paid for a player at the time.

The Rossoneri had to beat the competition of Europe’s elite clubs to sign the Spaniard but Javi Moreno was a total flop in his sole campaign in Italy.

The striker struggled immensely and scored only 2 goals that season. 

Javi Moreno

At the end of the season Javi Moreno was sold to newly promoted Atletico Madrid but with similar results.

While many players have left their mark with AC Milan winning many trophies along the way, others have failed to live up to expectations.

Bakaye Traore – CM

The last name, and most recent player to have dressed the glorious Red and Black jersey is that Bakaye Traore. In a period when AC Milan were signing only free agents the former Mali international too was signed on a free transfer from Nancy.

It’s impossible to understand what Adriano Galliani saw in this player. After 7 appearances, all of them off the bench, Traore moved again on a free transfer to Bursaspor.

Bakaye Traore

After two season in Turkey his contract was terminated and he had to retire at the age of 30. According to the Rossoneri fans, Traore is one of the least technically gifted players who have ever played for AC Milan.


READ MORE: “I left Milan because i was not worthy anymore”