AC Milan: 10 Worst Transfer Signings of All Time

AC Milan are one of the greatest football clubs of all time and have won everything the game has been able to throw at them.

They have a rich history from winning their first Serie A title in only their second year of existence in 1901 to becoming the first Italian side to compete in the European Cup in 1955.

They have won the Scudetto a phenomenal 18 times since 1901, and even more impressively, they have taken the "trophy with big ears," the Champions League, back to Milan seven times.

You can see their rich history without even taking their other trophy wins like the UEFA Cup, Intercontinental Cup, Coppa Italia and the Super Coppa Italia into account.

In short, AC Milan is an incredibly successful club.

As a result of being such a special club they have had their fair share of special players too—the likes of Paulo Maldini, Marco van Basten, Ruud Gullit, Franco Baresi, Andrea Pirlo, Giovanni Trappatoni and the list goes on and on.

But behind every great team and trophy, there is always a guy left on the sidelines scratching his head wondering where it all went wrong.

This article is not dedicated to the heroes like Maldini and co., it is a testimony to the nearly man, the almost made it—the worst transfers the club has ever made.

Read on, and be sure to leave who you think are Milan's worst players of all time in the comments below.

10. Gianluigi Lentini

It might be harsh, but its no surprise that Gianluigi Lentini makes the list as one of the worst AC Milan signings of all time.

Milan, in a state of trying to build on the glory days of van Basten, Gullit and Rijkaard signed the modest Torino based winger in the summer of 1992 for a then world-record fee of £13 million.

The transfer drew such world wide attention, mainly because of the fee and partly because of the player's lack of status within the game, that even the Vatican felt it should make a comment on the deal by issuing a statement condemning the money involved, calling the deal "an offence against the dignity of work."

Strong words from the Holy See, especially because the Pope at the time, Pope John Paul II, was an avid football fan!

Anyways, we're getting side-tracked. Lentini was never worth the £13-million transfer fee even though he had a pretty decent first season, winning the Scudetto and losing the Champions League final.

However, tragedy was to strike during the summer in 1993 when Lentini crashed his car in an horrific accident.

He fractured his skull and spent almost three days in a coma before recovering.

Unfortunately for AC Milan, the player never recovered his ball-playing skills at the highest level, and he never got a chance to repay that huge transfer fee as he was sold to Atalanta for just £2 million in 1996.

9. Oguchi Onyewu

Oguchi Onyewu, a Team USA international, enjoyed a torrid time with the Rossoneri between 2009 and 2011 and did not feature in one single league game for the Italian giants.

Considering his previous experience with Metz, Standard Liege and Newcastle United the very fact that AC Milan signed the player in 2009 was a shock to many.

Even though the giant lumbering centre half was not suited to the style of football in Italy, he deserves some credit because he missed an entire season through injury, and then when Milan offered to extend his contract by one season, the Clemson University graduate proved to be a solid guy by offering to take no salary during that season.

Unfortunately for Onyewu, he was given a free transfer to Sporting Lisbon in 2011.

8. Javi Moreno

Not having the greatest of scouts in 2001 left AC Milan with something like egg on their faces after they signed Javi Moreno following an impressive season with Alaves.

The diminutive striker was in top form between 2000 and 2001 and helped fire the lowly Spanish club to an unprecedented UEFA Cup final where they were beaten by Liverpool 5-4 in an incredible game of football.

Under pressure to reproduce the glory days of yesteryear, AC Milan's management failed to look into Moreno's past, and had they done as much, they would have realized that the striker was in a golden patch during that season, having never produced that form previously.

Anyway, Milan went on to sign the player and he went on to struggle in Serie A to little surprise, and after just 16 games, he was sold back to Spain and Atletico Madrid.

7. Winston Bogarde

If there is one name that is synonymous with sitting on the bench while collecting a giant pay check it is Winston Bogarde.

The versatile defender was part of Louis van Gaal's exciting Ajax side that swept all before them on the way to winning the Champions League in 1995.

From there, every single player and the manager were on the scouting books of every major European team and Bogarde was no different.

A classy defender who could switch from centre half to full back on either side at the flick of a switch, Bogarde moved to AC Milan, who had seen Franco Baresi retire in 1997.

Unfortunately for Bogarde and for AC Milan and for Barcelona and Chelsea much later, they were signing a player who had already reached his goal when he won the Champions League. From then on, he wanted to live on easy street.

Luckily for Milan, Barcelona, then managed by van Gaal, decided to buy the player and hence remove the albatross-like financial burden from around MIlan's neck.

Things slightly improved at Barca with Bogarde managing to improve upon his miserable record of just three games while at Milan to 41 games while at the Nou Camp over three years.

Then, and somewhat amazingly, Chelsea offered the defender a phenomenal £10 million contract across four years.

Needless to say Bogarde signed, and only played nine games in four years, while collecting a huge wage.

6. Roque Junior

Despite having gained 50 caps as a Brazilian international, Roque Junior will always be a reminder of bad defending for AC Milan fans.

Slow, cumbersome and not a great passer, Roque Junior still had something of a stellar career in Brazil before his ill-fated move to Milan in 2000.

However, that move saw his career pretty much derail after that.

He somehow managed to play 44 games for Milan, winning the Champions League in 2003 in the process and the World Cup in 2002, but the sheer amount of mistakes he made while playing for the Rosseneri mean he will always be remembered for the wrong reasons.

In fairness to Roque Junior though, he did have the sense to get injured during the 2003 Champions League final, meaning his own players avoided passing the ball to him and therefore he made no mistakes. So, he actually did quite well when you consider it.

He was moved on in 2003 where he enjoyed a disastrous five games with Leeds United. By the time his career finished in 2010, he had only manged to play 62 games in seven years from leaving Milan.

5. Ibrahima Ba

Ba joined AC Milan in 1997 amidst great fanfare after impressing in Ligue 1 with Le Harve and Bourdeaux.

Upon closer look, it was one of the worst transfers the club ever made, as the French league was quite poor at the time, while Serie A was easily one of the top leagues in the world.

Having scored just 14 goals in 163 games across six seasons in France, Ba surprised Milan by scoring only one goal from 56 games while in Serie A.

With the obvious step up in skill providing a huge hurdle for the French youngster, he saw his confidence drop, and he went from being a certainty for World Cup France 1998 to being dropped from the squad completely.

From here, his club form dipped dramatically and he never managed to regain that spark that had once marked him out as one of Europe's best prospects.

4. Chedric Seedorf

Why AC Milan signed Chedric Seedorf in 2008 is one of the great mysteries of modern football.

An Ajax product just like his two brothers Clarence and the lesser-known Jurgen, Seedorf spent the vast majority of his career from 2001 training, not playing, with teams in Serie B, C and in Belgian Division 2. So, when Milan signed the player in 2008, it really was a shock.

Needless to say young Chedric never played a game for the club and was almost immediately sent on loan to Evian in France.

At the last count he was playing for Monza in Serie C.

3. Oscar Washington Tabarez

Oscar Washington Tabarez may have led Uruguay to the Copa America title in 2011 and to fourth at World Cup 2010 and he may be enjoying the best period of his long career, but his time at AC Milan in 1996 will always be remembered by the Rosseneri as a black spot in the club's history.

Fabio Capello had just left the club for pastures new at Real Madrid, after guiding Milan to four titles, 1991-92, 1992-93, 1993-94, 1995-96, a Champions League triumph in 1994 and numerous secondary cup titles during his incredibly successful run as manager.

So when the little-known Oscar Washington Tabarez was chosen to succeed Capello, alarm bells started ringing immediately at the San Siro.

Under the Uruguayan, things started off fine for the reigning champions with four wins and a draw from their first six games, but a crushing 3-0 defeat to AS Roma on October 13, 1996 sent Milan into free-fall.

From there, confidence dropped and the Rosseneri only managed to pick up two more wins from the following 11 games before Tabarez was sacked.

He lasted just 22 games at the San Siro and had won just eight of them.

2. Digao

In July 2004 AC Milan signed one of the worst players ever to play in Italy, never mind the club, when they brought in Digao from Sao Paulo for an undisclosed fee—which was probably just as well.

The 19-year-old Brazilian was signed with the hope that he would grow into a defender of some class, but he was sent out on loan almost immediately upon arrival to Sampdoria.

Not featuring even once during the 2004-05 season, the youngster was then sent on loan to lowly Rimini where his influence was only slightly less negligible.

He then spent the next seven years traipsing across Europe on loan, before eventually, in 2011, settling back into some semblance of football in Portugal with the almost-unknown Penafiel.

You may ask yourself why AC Milan signed this player and then kept him on the books for so long while obviously having no intention of putting him into the team?

The answer is simple: his brother is none other than Ricardo Izecson dos Santos Leite or Kaka to you and me. 

Kaka signed for Milan from Sao Paulo in 2003 and was then sold to Real Madrid in 2009.

1. Luther Blissett

Luther Blissett is a legendary player at AC Milan, and despite being held as the worst signing and probably worst player ever to play for the Rosseneri, he is loved across the world.

Prior to his sensational £1 million transfer from Watford to Milan in 1983, the striker was an integral part of Graham Taylor's long-ball side and scored a superb 27 goals as the Hornets finished second to Liverpool in their first ever season in the top flight.

It was here that Blissett caught the eye of AC Milan scouts. Scouring Europe for a player that could lead them to the Scudetto, they went to Vicarage Road to see this surprise English Division 1 team and came back with rave reviews of the dangerous young Jamaican kid up front.

It all gets sketchy here though, as legend has it that when the club came back to sign the player they had previously scouted, they got Blissett instead of a young up and coming John Barnes!

To make a short story even shorter, Blissett lasted just one season in Serie A before he was sold back to Watford for half the initial transfer fee.

Now why is Blissett so loved around the world?

His name has become synonymous with anarchists who want to bring down corporations and huge organizations and from Europe to South America, and it is no surprise to see his name graffitied on a wall somewhere!

To go even further, four Italian authors used the nom de plume of Luther Blissett to write the worldwide best-selling book; Q!