AC Milan transfers: The five most painful Rossoneri exits that came before Tonali to Newcastle

Sandro Tonali's move to Newcastle was not an easy one to stomach for AC Milan fans, but which other departures have caused similar or worse pain down the years?


When you’re a club with the stature of AC Milan, it is no surprise that some of the world’s finest players have passed through the doors of Casa Milan throughout the club’s history.

Enriched in both domestic and European success, Milan’s triumphs across the decades have enabled them to attract elite footballers from across the globe. However, every story must come to an end, and sometimes when the book is closed on a club legend or an academy prospect, it’s a hard pill to swallow for the supporters who adore them.

In the wake of Sandro Tonali’s departure to Newcastle United in the Premier League, a player many thought would go on to captain Milan, here are five times that players have left Rossoneri fans feeling bereft, according to La Gazzetta dello Sport.

Key players who have left AC Milan

5 – Thiago Silva to PSG

Thiago Silva in action for AC Milan against Thierry Henry. [Getty]

Almost parallel to the recent exit of Sandro Tonali, Thiago Silva was headhunted by the newly Qatari-backed Paris Saint-Germain in 2012. Exiting the San Siro alongside Swede Zlatan Ibrahimovic, Milan had two of their key players pinched by PSG just a year after winning a Scudetto.

For the Brazilian, a €38 million fee was received for his services (a rather large price in the market a decade ago) and that helped balance out the club’s finances but killed their ambition. At the time of the sale, Silva was one of the most coveted defensive prospects in Europe, carrying on Milan’s tradition of having an excellent defensive department.

Losing him almost completely symbolised their downward trajectory over the years that were to follow.

4 – Andrea Pirlo to Juventus (End of contract)

Andrea Pirlo in action for AC Milan. [Getty]

After 401 appearances for the Rossoneri, Andrea Pirlo left following the expiry of his contract back in 2011, eventually joining Serie A rivals Juventus. Pirlo and Milan enjoyed much success together, particularly under coach Carlo Ancelotti, including two Scudetti (2004, 2011) and two Champions League wins (2003, 2007).

After attaining club legend status following 10 years at the San Siro, Milan had age concerns about the 30-year-old and only offered a one-year contract extension, which Pirlo was devastated about, having the preference to stay with the club for longer.

Ultimately, Pirlo went on to massively strengthen rivals Juventus, being a key factor in the club’s revival where he won a Scudetto every year up until his departure in 2015.

3 – Kaka to Real Madrid

Kaka playing for AC Milan in 2009. [Getty]

A Ballon d’Or winner and a consistent ray of flair amongst a team of excellency, Kaka was a sale that stung for Milan and the supporters. Only two years after he was crowned the best player in Europe, 2009 saw the Brazilian become a Galactico as he swapped Italy for Spain, moving to Real Madrid for €67m.

The state of the world’s economy hit Milan like many others back in 2009, being cited as one of the key reasons for the sale. Coinciding with personal achievements, Kaka won a Scudetto, a Champions League and a FIFA Club World Cup during his time at the San Siro.

The exit not only signified the departure of one of Milan’s most beloved players, but also that the best players in the world will go and ply their trade elsewhere, despite the success.

2 – Frank Rijkaard and Ruud Gullit to Ajax and Sampdoria

(Left-right) Frank Rijkaard, Marco van Basten and Ruud Gullit at AC Milan. [Getty]

The inseparable Dutch duo. Not a single departure, but the Rossoneri have had the unfortunate privilege of seeing multiple key players leave at once over the course of their history, and this one hit twice as hard.

The pair won two Champions League titles and two Serie A titles amongst many other team and individual honours during the height of the Silvio Berlusconi era, a golden time in the late 1980s and early 1990s.

Both Frank Rijkaard and Ruud Gullit were integral to Milan’s success during this period, and their exits foreshadowed this golden era’s conclusion. Rijkaard cited the reason for his departure as wanting to go out on top, at the pinnacle, as he returned to former club Ajax.

Gullit on the other hand, put it down to the lack of trust in him from the Rossoneri hierarchy due to his long-term knee injury.

1 – Clarence Seedorf, Gennaro Gattuso, Alessandro Nesta and Filippo Inzaghi – Botafogo, FC Sion, Montreal Impact and retirement

Clarence Seedorf playing for AC Milan. [Getty]

On one of the rarest occasions in Italian football history, four bonified club legends departed Milan at the same time, saying their farewells together.

In special fashion, all four players went on to either retire, or play out the rest of their careers (albeit short) outside of Europe. The four combined made a total of 1526 appearances for the Rossoneri, with all of them playing at the peak of their powers during their long stay, winning an abundance of silverware.

The San Siro was flooded with tears and hugs during their send-off on May 13, 2012, a testament to four expectational servants who gave blood, sweat and tears for the Rossoneri


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