Man City won transfer race for £32.5m deadline day signing who ended up in prison

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Manchester City made a major statement of intent on the day of their Abu Dhabi takeover in 2008 by signing Robinho from Real Madrid, right under their Premier League rivals' noses

Barclays Premier League, Manchester City Press Conference, Manchester City's new signing Robinho with manager Mark Hughes
Manchester City beat Chelsea to the signing of Robinho on transfer deadline day in 2008(Image: Manchester City FC via Getty Images)

One particular signing is credited as the catalyst for Manchester City's new trajectory, which has seen them win eight Premier League titles and the Champions League. On September 1, 2008, the Abu Dhabi United Group, spearheaded by Emirati Royal Sheikh Mansour, shifted the course of English football with their takeover of City.

On that same day, the new owners made a bold declaration of their ambitions by splashing out £32.5million on Brazilian forward Robinho. The winger, already an established star in Real Madrid's Galactico line-up, was a hugely exciting arrival, having been one of the world’s biggest talents prior to his 2005 move to the Santiago Bernabeu.

The transfer marked the start of City's strategy of attracting high-profile players and initiating a project that would rival and eclipse Manchester United in the following years. Seventeen years on, the Etihad club is undoubtedly the standout English team of the past decade, while the disgraced Robinho serves a lengthy prison term.

The 41-year-old was found guilty of rape by an Italian court in 2017. After numerous appeals and attempts by the Italian court to extradite Robinho, who maintained his innocence, he was found guilty of participating in the gang rape of a woman at a Milan nightclub in 2013.

He only began serving his nine-year sentence in Brazil in March 2024, incarcerated in Sao Paulo's infamous Tremembe prison complex, known as the 'prison of the famous' due to its other high-profile inmates.

His off-field conduct has rightly overshadowed his glittering playing career, 18 months of which were spent at City. The scale of his move to what was then a mid-table side is something today's younger fans might not fully appreciate.

During the summer of 2008, Chelsea, already well-versed in making big-name signings under Roman Abramovich, had been frontrunners for Robinho, who voiced his desire to join the west London side.

Robinho celebrates for Man City
Robinho was the flagship signing of Manchester City’s revolution under Sheikh Mansour(Image: Getty)

But Real stood firm in their stance that the 24-year-old was not for sale, rejecting multiple Chelsea bids over the following weeks and effectively putting an end to their pursuit.

But City, with new financial clout provided by their Middle Eastern owners, met the valuation placed on Robinho by the Spanish giants at the eleventh hour on transfer deadline day, breaking the British transfer record in a deal worth £32.5m.

Robinho told City's official website at the time: "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 also 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.

 Brazilian footballer Robson de Souza (Robinho) attends a contract signing ceremony with Medipol Basaksehir in Istanbul, Turkey on January 05, 2019. Robinho has signed with Super Lig club Medipol Basaksehir for a 1.5-year contract.
Robinho lost his final appeal against a nine-year conviction in January 2019(Image: Getty Images)

"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."

Despite failing to meet expectations in Madrid, the forward hit the ground running at City, netting 15 goals and setting up nine more in his debut season under Mark Hughes. However, his early promise didn't last, and Robinho was allowed to leave on loan after less than a year and a half with the club, before finalising a permanent move to AC Milan at the end of the 2009/10 season.

He then had stints in China, Turkey and Brazil, with his last official club being his boyhood team, Santos, in 2020. His career ended with 100 appearances for Brazil, during which he scored 28 goals.

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