Chelsea were beaten by Man City to £32.5m transfer deadline day signing who ended up in jail

For Chelsea fans, the Robinho saga remains one of the most frustrating transfer stories of the Roman Abramovich era. In the summer of 2008, the Blues were in pole position to land the Brazilian, who made no secret of his desire to move to West London.

The club were so confident of pulling it off that Robinho shirts even went on sale at the Stamford Bridge megastore before the deal was wrapped up. However, Manchester City swooped in at the last possible moment, hijacking the transfer and altering the trajectory of English football in the process.

On September 1, 2008, Sheikh Mansour's Abu Dhabi United Group completed their takeover of City. Hours later, they flexed their new financial muscle by sealing a £32.5m deal with Real Madrid - who were furious with Chelsea's shirt-selling antics - for Robinho, smashing the British transfer record and making a statement that would define the next two decades.

The winger was already a Galactico at Real Madrid, once hailed as one of the most gifted players in the world after his 2005 move to the Bernabéu. For Chelsea fans, who had grown used to Abramovich delivering world-class arrivals, Robinho felt like the next piece of the puzzle - particularly with Brazilian boss Luis Felipe Scolari at the helm - and a player capable of adding even more flair to a squad already brimming with quality.

Instead, he became the face of City's oil-fuelled revolution. That transfer was the starting gun for City's era of excess. The signings that followed soon eclipsed Manchester United and shifted the power balance in Manchester. Seventeen years on, City have racked up eight Premier League titles and a Champions League, while Robinho himself is remembered for very different reasons.

The now 41-year-old was convicted of rape by an Italian court in 2017, relating to an assault in Milan four years earlier. After lengthy appeals and extradition wrangles, he finally began serving his nine-year prison term in Sao Paulo's notorious Tremembe complex in March 2024.

His disgrace off the pitch has overshadowed what should have been a glittering career - including an 18-month spell at City. But even if his time in Manchester was brief, the significance of that deadline-day coup is something younger Chelsea supporters may not fully grasp today.

The truth is, Robinho wanted to come to Stamford Bridge. He pushed for the move, but Real Madrid ultimately kyboshed it, despite agreeing a deal with the Blues.

City, armed with Abu Dhabi wealth, pounced at the last possible moment, agreeing to Madrid's demands and presenting Robinho as the marquee face of their new project. At the time, he said on City's official website: "I knew that Manchester City is a very big club, there's a great team there already and this is an exciting project.

"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."

He told the Mirror: "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."

Robinho initially impressed with 15 goals and nine assists in his first campaign - including, ironically, a debut goal against Chelsea. But he quickly faded, falling out of favour and heading to AC Milan in 2010. From there he drifted through stints in Turkey, China, and finally back to Santos, finishing with 100 Brazil caps and 28 international goals.

For Chelsea fans, though, the memory of Robinho is less about what he did on the pitch and more about what might have been.

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