08/31/2026
The Most Bizarre Deadline Day Deals
1/3 Ronaldo, Inter to Real Madrid (2002)
The transfer was agreed on the 31st of August 2002, hours after Real Madrid lifted the UEFA Super Cup the night before. The deal caused real chaos on both ends of the transfer before being finalized.
Ronaldo's relationship with Inter manager Héctor Cúper, had gone sour and he gave club president Massimo Moratti a choice. Cuper out or I'm leaving. Moratti chose Cúper.
Moratti later furiously accused Ronaldo of premeditating the whole exit, claiming that he made the decision to leave on the day he won the World Cup, leaving Inter for "a handful of loose change" and that the complaints about Cúper were just an excuse.
Inter lost the best striker in the world with almost no time to find a replacement. They spent the whole night rushing to register Hernán Crespo, a transfer which was declared off earlier on that same day. Inter somehow managed to turn it around before the deadline struck.
When Ronaldo was in Madrid, the clubs still had some loose ends to fix. The agreement had a clause letting Inter choose, by January, between taking either Santiago Solari or Steve McManaman from Real Madrid as extra compensation, or receiving an additional €10 million in cash.
Months of public back and forth followed. Before Solari's move was finalized. Moratti declared his arrival, then reversed his statement, then reportedly ignoring a fax from Real Madrid formalising the move while Inter's transfer chief openly contradicted Real Madrid's director Jorge Valdano' statements about where things stood.
Moratti later publicly calculated that with Crespo, Fabio Cannavaro and a potential resale of Solari, the Ronaldo transfer had effectively netted Inter around €53 million in total value, adding that he considered three quarters of Ronaldo's 2002 Ballon d'Or to belong to Inter, since that's where he had played for the bigger part of the year.
Ronaldo arrived in Madrid weeks after winning the World Cup in Japan and South Korea, and joined the Galácticos team with superstars Zidane, Figo, Raúl and his friend Roberto Carlos. He was immediately brilliant, scoring 30 goals in 44 matches across all competitions and helping Real Madrid win the title in 2003.
He was also partying hard in Madrid. Teammate Iván Helguera later described some of the parties held at Ronaldo's house, on one occasion chartering an entire bus full of women for the night. Ronaldo himself his routine of playing a match on Saturday, flying to Paris that same evening, partying through Sunday night, then catching a 7am flight back to Madrid in time for training at ten.
He has said the stories had become exaggerated and he always protected his body and never let it affect his level on the pitch, though his results eventually declined over the years.
By the time Fabio Capello arrived as manager in 2006, Ronaldo weighed 94 kilograms, and Capello later said teammate Ruud van Nistelrooy came to him directly to complain that the dressing room smelled of alcohol. Capello pushed for his exit that same season, but still called him the greatest individual talent he ever coached.
