Chelsea lost £32.5m deadline day transfer race for player who ended up behind bars

For years, Chelsea had the biggest financial muscle in world football - but one dramatic day in 2008 changed everything and signalled that a major shift was coming

One signing, more than any other, is often seen as the moment the balance of power in English football shifted - away from Chelsea and towards Manchester City. Over the past two decades, both clubs have built modern dynasties, spending lavishly and hoovering up trophies like it's going out of style.

Under Roman Abramovich, Chelsea transformed from entertaining nearly-men into a dominant force, not only in English football but across Europe. For several years, their financial muscle was unmatched. Then, in September 2008, everything changed.

When City were taken over by the Abu Dhabi United Group, led by Emirati royal Sheikh Mansour, few could have predicted just how immediate the impact would be. Within hours of the takeover - completed on transfer deadline day - City sent a chilling message to the rest of the league by signing Brazilian superstar Robinho from Real Madrid for £32.5million.

What made the move even more significant was that it came at Chelsea's expense. The Blues had been in negotiations with Real Madrid for weeks and believed they had a deal in place. Instead, City pulled off one of the most audacious transfer hijacks in Premier League history, snatching Robinho from under their rivals' noses and, in the process, announcing to the footballing world that a new power had arrived - and it had no intention of waiting around.

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What came next was a wave of investment that would soon surpass even Chelsea's lavish early years under Abramovich. It might have taken City four years to lift their first league title, but once that hurdle was cleared, success followed in abundance.

Now, 18 years after the takeover, they are firmly established as the dominant power in English football and a perennial heavyweight on the European stage.

Ironically, although Robinho's signing triggered a dazzling, silverware-filled sequence of events, the former Brazil forward contributed little to City's achievements on the pitch. He did score memorably on his debut against Chelsea, yet beyond that moment Robinho struggled badly in Manchester.

His stay lasted less than two years before a move to Milan, where, some time later, both his career - and his personal life - would unravel completely.

The now 42-year-old was found guilty of rape by an Italian court in 2017. After years of appeals and unsuccessful attempts by Italian prosecutors to extradite him, Robinho, who denied the accusations, was convicted of involvement in the gang rape of a woman at a Milan nightclub in 2013.

He began serving a nine-year prison term in Brazil in March 2024 and is currently being held at Sao Paulo's infamous Tremembe prison complex, frequently described as the 'prison of the famous' due to its high-profile inmates.

His actions away from the sport have understandably overshadowed anything he achieved on the field, including his 18-month spell with City. Even so, Robinho's arrival at the Etihad Stadium still ranks among the most astonishing transfers in English football history.

At the time, speculation spread that Robinho believed he was signing for Manchester United rather than their local rivals, but he dismissed those claims once the deal was completed.

"I knew that Manchester City is a very big club, there's a great team there already and this is an exciting project," he told City's website. "I liked the project, and when City made the offer to Real Madrid, I decided to come here. I liked the plans that Manchester City have and I want to succeed with them."

Speaking to the Mirror, he added: "I could understand why questions were asked about why I joined City last season because here was a club that had not celebrated any kind of success for many years.

"It was said that I had come purely for financial reasons, that I had forgotten about my ambitions because of money. I said at the time that I signed because I had been sold a vision of Manchester City becoming a powerful club, not just in England, but throughout the rest of the world.

"Nobody was interested in listening to me a year ago but I think they will have to believe me when they see what is happening to City now. I think we are now on the brink of something very special. I want to win the championship this season. I think we can challenge for the title.

"Maybe it is still too soon and we have to have more time to develop as a team, but I do know I will be part of a team that will bring excitement to everyone.

"Our attacking options are the best of any team. Signing Carlos Tevez, Roque Santa Cruz and Emmanuel Adebayor means I'll get even more opportunities to express myself because opponents will have other dangers to think about.

"Even our midfielders only know one way to play - to attack. Look at the threat we have in Shaun Wright-Phillips, Stephen Ireland and Martin Petrov. This is something very special."