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5 most heartbreaking transfers of all time

Lionel Messi Farewell Press Conference at Barcelona
Lionel Messi Farewell Press Conference at Barcelona

The transfer window represents an opportunity for teams to bolster their ranks. It is a time where clubs that have identified their shortcomings reach into their pockets and sign players who will improve the team. While big clubs are used to making marquee signings, smaller clubs are accustomed to losing their best players.

But that needn't always be the case. Players can move between teams of similar stature. There have also been transfers that have left fans of a team crestfallen or heartbroken. This usually happens when a club hero decides to leave. Worse yet, they could join a rival and strengthen them in the process.

It's hard for football fans to pardon such actions but that's just the way things work out in the transfer window at times. Without further ado, let's take a look at five of the most heartbreaking transfers of all time.


#5 Robin van Persie (Arsenal to Manchester United)

Manchester United v Aston Villa - Premier League
Manchester United v Aston Villa - Premier League

Robin van Persie was signed by Arsenal from Feyenoord in 2004 for €4.5 million. He gradually established himself as one of the finest strikers of his generation and spent eight years with the Gunners.

But in the summer of 2012, Van Persie pulled off the unpardonable as far as Arsenal fans are concerned. He secured a switch to rivals Manchester United on a deal worth €30 million. The prevailing narrative was that the Dutchman had grown frustrated over the lack of trophies at the Emirates and wanted to play for Sir Alex Ferguson.

Van Persie won the Premier League with Manchester United in his first season at the club. He was the recipient of the Premier League Golden Boot as well, scoring 26 goals in 38 appearances. He also provided 15 assists in the league and was a brilliant signing for the Red Devils.

In an interview with Premier League productions in 2020, Van Persie said:

"Ferguson made the difference for me in my choice to choose Manchester United. Because of the way he manages, the stories I heard, because of the players that were there.
"I really wanted to win and when I look at that team of Giggs, Carrick, Scholes, Vidic, Ferdinand they were all winners, they won it all. I was like ‘I want to be part of that’. I was in that period of my life where I felt like a winner but I wasn’t so I had to win. I needed to go to a team that knew how to win."

#4 Roberto Baggio (Fiorentina to Juventus)

Roberto Baggio of Juventus and Franco Baresi of AC Milan
Roberto Baggio of Juventus and Franco Baresi of AC Milan

Roberto Baggio, also known as Il Divin Codino (The Divine Ponytail), is a Ballon d'Or winner and one of the finest playmakers in the history of the game. After spending five years at Fiorentina and being hailed as a hero there, Baggio moved to bitter rivals Juventus in 1990 on a deal worth £8 million.

Fiorentina fans were infuriated by the move and they took to the streets to riot. 50 people were injured and Baggio was forced to issue a reply to fans. He said:

"I was compelled to accept the transfer."

It was a transfer that neither the player nor the fans really got over. Baggio once refused to take a penalty for Juventus against Fiorentina, claiming La Viola goalkeeper Gianmatto Mareggini knew him too well.

Juventus fans didn't appreciate the fact that Baggio picked up a purple Fiorentina scarf that was thrown onto the field later in the game. The Fiorentina fans loved it. Despite winning the Serie A and the Coppa Italia with the Bianconeri, Baggio has said that deep in his heart, he is always purple (Fiorentina's colour).

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