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The Vinícius Jr contract situation is nearing its resolution, one way or another.
Having returned from a rest period following his World Cup campaign, the Brazilian star has entered fresh discussions with the club as they push to finally seal a new agreement that would keep him beyond next summer.
Reports indicate this will be the decisive meeting between player and club, who have been deadlocked since talks broke down last year, with both parties unable to bridge the gap in wage demands.
Publicly, Vinícius Jr has consistently professed his commitment to Madrid, but that loyalty may be put to the test by a 'final offer' that, though improved, still doesn't reach the figures that were circulating earlier this summer. Arsenal are monitoring the situation very closely.
It would be a seismic, headline-dominating move for the 26-year-old to reject Madrid and effectively draw the curtain on his time at the world's most prestigious club.
Former Real Madrid star Predrag Mijatović has urged Vinícius not to make that very mistake, sharing with Cadena Ser how he came to deeply regret his own departure from Los Blancos following a falling out back in 1999.
"What have I done with my life? I was in football paradise," the 1997 Ballon d'Or runner-up recalled thinking.
"When you want to return, there's simply no going back, obviously."
But is life after Madrid truly all misery and regret? Here are seven players who departed the club in their prime and what followed.
1. Predrag Mijatović (1999)
Acquired from Valencia in 1996, the Yugoslavia international played a pivotal role in the 1996–97 La Liga title win before netting the decisive goal in the Champions League final—Madrid's first European Cup in more than 30 years—the following campaign.
However, after a falling out with manager John Toshack, the striker opted to depart for Fiorentina after only three seasons at the club.
The forward later confessed to regretting the move, stating: "It's better to be second choice at Real Madrid than to be number one at any other team in the world, I'm telling you."
2. Claude Makélélé (2003)
Arguably the most notorious transfer decision in Madrid's history, defensive midfielder Makélélé was offloaded to Chelsea in the summer of 2003 after clashing with president Florentino Pérez over a contract improvement request.
Following a bitter dispute, Pérez dismissed the French star with the cutting farewell: "Younger players will come who will make everyone forget about Makélélé."
The president's power play turned out to be a catastrophic miscalculation. Madrid struggled without a midfield anchor and went four years without winning a major trophy.
Makélélé, meanwhile, flourished in England, claiming the Premier League title twice and almost single-handedly elevating the status of holding midfielders.
3. Robinho (2008)
Brought in as a final gamble by Pérez as the first Galácticos era unravelled, the young Brazilian was volatile yet productive across two title-winning campaigns at the Bernabéu.
However, he grew increasingly vocal about a perceived lack of playing time, compounded by then president Ramon Calderón's thinly veiled intentions to use him as a bargaining chip in the pursuit of Cristiano Ronaldo.
Robinho pushed hard for an exit and was eventually sold to Manchester City as the new ownership's marquee signing.
Yet he had moved on again within eighteen months, as issues with work ethic and attitude trailed him throughout what became a nomadic career that never lived up to the early promise.
In 2017, he was convicted of sexual assault and sentenced to nine years in prison.
4. Gonzalo Higuaín (2013)
"You suffer when you don't get to play regularly, as you do when you have to share minutes with Karim Benzema," Higuaín revealed following his departure from Madrid to Napoli in the summer of 2013.
The striker netted a remarkable 121 goals in 264 appearances for Los Blancos, yet could never fully cement himself as the undisputed first-choice No.9, constantly competing for the role with Benzema.
At Napoli, he was unquestionably the focal point, scoring 91 goals in 146 matches—including 38 in his final season there.
The Argentina international went on to claim three Serie A titles following a controversial switch to Juventus, establishing himself as one of the world's most lethal finishers.
Nevertheless, given Benzema's eventual achievements, it was difficult for Madrid supporters to argue their club had made the right call.
5. Mesut Özil (2013)
Just 24 at the time of his switch to Arsenal and already regarded as one of Europe's finest playmakers, Özil's exit left many feeling the German had plenty more to offer at Real Madrid.
Özil took aim at the decision-makers at the Bernabéu over his departure as he explained his reasons for seeking a transfer, following a breakdown in contract talks with Pérez.
"Over the weekend, I was convinced I would remain at Real Madrid, but then I realised I no longer had the trust of the coach or the club hierarchy. I need that trust to perform, and that's what I felt from Arsenal, which is why I made the move," he said pointedly.
Özil became a cult figure at Arsenal, winning three FA Cups, though league or European glory eluded him. Madrid, meanwhile, evolved into a midfield without a No.10, which ultimately yielded four Champions League titles in five years.
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6. Ángel Di María (2014)
Just weeks after being named Man of the Match in the 2014 Champions League final, Di María had departed Real Madrid for Manchester United in what was then a British transfer record.
The Argentina star was another victim of Pérez's uncompromising contract negotiation approach, with World Cup sensation James Rodríguez brought in as his replacement.
Di María later revealed to The Players' Tribune that Madrid had coldly pressured him into missing the World Cup final to safeguard their asset ahead of the sale, as he was carrying an injury at the time.
While his stint at United proved disappointing, Di María rebuilt his reputation as one of football's finest attacking players at Paris Saint-Germain, where he collected numerous titles and remains the club's all-time leading assist provider.
He later had another shot at World Cup glory, scoring against France in the Qatar 2022 final.
7. Cristiano Ronaldo (2018)
During the post-match celebrations of the 2018 Champions League final victory, Ronaldo dropped a bombshell while addressing reporters on the pitch in Kyiv.
"It has been wonderful playing for Real Madrid," he said.
The club's all-time leading scorer, five-time Ballon d'Or winner and Champions League top scorer for six straight seasons was announcing the end of his Madrid chapter.
Well into his thirties and pushing for another lucrative contract extension, Pérez chose to cash in on the forward, who moved to Juventus that summer for €100 million.
The Portuguese icon continued to find the net at a remarkable rate, claiming two Serie A titles along the way, yet the extraordinary heights he had scaled at Madrid were never quite recaptured.