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#3 Cristiano Ronaldo (Real Madrid to Juventus) - 2018
Cristiano Ronaldo was already a bonafide world-class player when he joined Real Madrid from Manchester United in the summer of 2009. However, few would have predicted the dizzying heights the Madira native would reach in the colors of Los Blancos.
Over the next nine years, Cristiano Ronaldo redefined what was previously thought possible on the field of play. He was the catalyst for the most successful period in Real Madrid's modern era.
Real Madrid are the biggest club in the world, and the Santiago Bernabeu is the dream destination of millions of footballers around the world. It was simply unfathomable that their prized asset would leave the Spanish capital while still in his prime.
However, that proved to be the case when Ronaldo - fresh from inspiring Los Blancos to a three-peat UEFA Champions League crown - joined Juventus on a nine-figure deal in 2018.
Zinedine Zidane's shock resignation after the UEFA Champions League final was the precursor to Ronaldo's unexpected move away from the Bernabeu.
There were also reports that the Portugal international had fallen out with club president Florentino Perez, and this played a role in his departure.
Real Madrid have not been the same since the Madeira native's exit, with all his potential replacements failing to perform at the levels expected.
#2 Iker Casillas (Real Madrid to Porto) - 2015
Real Madrid are notoriously infamous for treating club legends badly. However, the manner in which they handled Iker Casillas' departure was shocking to even their biggest detractors.
The former Spain international had been at Real Madrid since making his debut in 1999. He went on to become a mainstay as the club won several trophies over the next two decades.
In his prime, Casillas was widely regarded as the best goalkeeper in the world and earned the affectionate nickname 'Saint Iker' from fans of the club.
However, mistakes began to creep into his game in the latter part of his career, and this saw him lose his starting spot in the team.
That does not, however, excuse the shambolic way in which Real Madrid announced his departure from the club.
His parents claimed Florentino Perez forced him out of the club, and a tearful Casillas bade goodbye to an empty Bernabeu in a hastily conducted press interview.
All his teammates had left on a pre-season tour, and Casillas was forced to face the press alone and announce his departure to Porto.
Contrasts were drawn with Xavi's emotional sendoff at Barcelona a few months prior, with Camp Nou having a carnival atmosphere to bid farewell to one of its greatest servants.
#1 Lionel Messi (Free Agent) - 2021
Barcelona have been in shambles over the last few years, but they have hit an all-time low in the bundling of Lionel Messi's contract renewal.
The Argentina international ran down his contract last season, having earlier threatened to leave the club in the summer of 2020.
That debacle proved to be the straw that broke the camel's back in Josep Bartomeu's disastrous presidency, and he resigned shortly after.
The next presidential election was held on the backdrop of Messi's future. Current president Joan Laporta was elected on the basis of his assurance of the 34-year-old's continued stay at the club.
The contract renewal was believed to be a mere formality, and initial reports emerged that a new deal had been agreed in principle pending an official announcement.
However, a spectacular turn of events led to the club announcing their iconic player's departure on Thursday evening, leading to a meltdown on social media.
Lionel Messi has been associated with Barcelona for over two decades and is inarguably the greatest player in the club's illustrious history.
The idea of the Rosario native wearing colors other than those of the Blaugrana was previously unimaginable, and it was taken for granted that he would retire at the Camp Nou.
However, a combination of several factors, chiefly Barcelona's mismanagement, has ensured that this will not be the case.
Also See: Seven European clubs to win a treble
