Former Real Madrid midfielder Luka Modric named his pick for the “toughest manager in the world” who “made Cristiano Ronaldo cry.” From the outside looking in, such a feat would seem almost impossible for a player obsessed with winning, whose mentality has long been viewed as indomitable and who some even credited with managing Portugal from the sidelines during their famous Euro 2016 triumph.

Together, Modric and Ronaldo boast 34 and 36 trophies respectively across their illustrious careers, sharing a dressing room and starting eleven during four Champions League triumphs. As for Modric, he remains the only player to win the Ballon d’Or other than Ronaldo and Lionel Messi during a 13-year stretch between 2007 and 2021.

But it wasn’t just their superstar ability that carried them to such heights, and plenty of credit must be given to the managers who shaped them along the way. Still going strong at 41 with AC Milan, Modric has recalled one such figure - a manager who struggled at the Bernabeu, but nonetheless left a lasting impression through his uncompromising, stern approach.

Modric: Jose Mourinho Once Made Ronaldo Cry

In a wide-ranging interview with Italian newspaper Corriere della Sera, Modric discussed his relationship with the most prominent managers in his career, including Carlo Ancelotti and current boss Massimiliano Allegri. But the Croatian named Jose Mourinho the toughest of the three, having seen him reduce one of the best players in history to tears. He recalled:

The legendary midfielder - up there with the best since 1990 - then went on to reveal his favourite manager, and there was no surprise that he picked Carlo Ancelotti, who is the current Brazil head coach. "It’s hard to find the words. For his way of being, not just for his qualities on the bench," he said. "We talked many times about Milan and AC Milan when we were in Madrid.

"This place [Milan] was unique for him too. I remember when I met him. I was alone in the city. He called me and said, 'Come on, come to dinner with me.' We talked for hours, about everything. Football, family, life. Usually, coaches don’t trust their players. He does.’"

Mourinho's First Real Madrid Spell: Short and Fraught With Issues

Mourinho and Ronaldo share a complex, layered relationship, shaped by both glittering success and underlying tension. The two Portuguese icons worked together at Real Madrid from 2010 to 2013, a spell that delivered a La Liga title, the Copa del Rey, and the Supercopa de Espana.

Under Mourinho, Ronaldo took his game to another level, enjoying some of the most prolific seasons of his career - including a then club-record 60 goals in the 2011/12 campaign. Yet, despite the silverware and the goals flowing freely, cracks began to show during Mourinho’s final season in 2012/13, and things soon imploded. Reports suggested tensions stemmed from his relentless demands and his willingness to air criticism publicly in a dressing room already known for its bloated, hard-to-contain egos.

One flashpoint reportedly came when Mourinho berated Ronaldo for failing to follow defensive instructions, sparking a heated exchange between the pair - an incident believed to be the moment Modric was referencing when he spoke of tears being shed.

Mourinho later admitted Ronaldo “thought he knew everything” and could be difficult to coach at times.

But whatever Ronaldo’s personal view of his compatriot, the numbers speak for themselves when it comes to Mourinho. Four World’s Best Club Coach awards, two Champions League titles, three Premier Leagues, a UEFA Cup and a Europa League underline a career that places him among the greatest managers in football history - a man who never allowed the pressure cooker of the Spanish capital to weigh him down as he has gone on to win a gluttony of silverware at most of the clubs he managed before and after.

It's very rare that Real Madrid ever return for one of their former managers - but that's precisely what the club's president Florentino Perez did in the summer of 2026.

Never one to shirk a challenge, 63-year-old Mourinho returned to the Bernabeu ahead of the 2026-27 campaign.