It’s also not the first time Ramos and Florentino have been at loggerheads over the fine details of a contract, although they’ve always worked things out. The pair have been close ever since Florentino made Ramos his first Spanish signing as president.
But never before has Ramos reached the final year of his contract without an agreement and never have the positions seemed so distant. Florentino has also shown throughout his time at the Santiago Bernabeu that he’s not afraid to put the interests of the club over the optics of a graceful exit of a club legend.
Fernando Hierro’s contract renewal negotiations were one of the first things that Florentino had to deal with upon becoming president, and the veteran was let go due to his age. Luis Figo, Florentino’s first signing as president, was sold to Inter a year before being released after he felt that Madrid didn’t want him to renew his deal.
Raul was a different case, leaving upon Jose Mourinho’s arrival due to a loss in sporting importance following the signing of Cristiano Ronaldo. His contract was liquidated a year ahead of time to enable him to join Schalke 04.
Iker Casillas’ departure was also difficult. Madrid wanted to sign David de Gea and they already had Keylor Navas on their books, and Casillas knew his time was up. The club him go on a free, but dispute arose over a settlement and compensating the salary difference between what he earned at Madrid and what he was going to earn at Porto.
Ronaldo, alongside Ramos, is the one to have given Florentino the most problems regarding his contractual situation. Each renewal was like a soap opera, with Ronaldo wanting the same annual renewals that Lionel Messi got at Barcelona. When the Portuguese left for Juventus in the summer of 2018, it was on somewhat acrimonious terms.