We’ve become used to Manchester City breaking the bank to sign some of the highest-profile players in the world. In fact, when they spent £41m to sign Nathan Aké, people hardly batted an eyelid. But in 2008, City spending that amount of money made sense to no one. 

Coming into deadline day for the summer transfer window in 2008, there were two major deals on the table. Dimitar Berbatov’s protracted move to Manchester United looked like it would finally be coming to a close, while Brazilian winger Robinho was on the brink of leaving Real Madrid and making the switch to Chelsea.

Like many great Brazilians to come before him, Robinho had grown up at Santos, the team he made his debut for in 2002 at the age of 18. There, he dazzled. He had a natural flair to his game, blended with pace and creativity, and it wasn’t long before he earned his first cap for Brazil, just a year after his debut. 

However, as a young Brazilian shining for Santos, there is always another burden placed on your shoulders. Like so many before him, and many more after, Robinho was given the title of ‘the next Pelé’. Players rarely benefit from those tags, and it didn’t help that the man himself said, “Robinho can surpass my own achievements. We have to thank God that another Pelé has landed at Santos.”

He also caught the attention of those overseas, and it was no surprise when he moved to Spain in 2005, signing for Real Madrid in a deal worth around £21m. He showed glimpses of his undoubted talent while in Madrid, but he was often a frustrating watch. Those glimpses were good – at times very good – but they just didn’t come often enough. 

There were signs of improvement, though, the longer he spent in Spain. He scored 15 times in all competitions in his final season at the Bernabéu, his best return in his three years there. However, there were troubles off the pitch. Promises by club president Ramón Calderón over a new contract had been broken not once but twice during the season, before Real tried to use him as a makeweight in a deal to bring Cristiano Ronaldo to Madrid. 

The lack of respect he felt from those high up at the club was too much for Robinho, who turned down Los Blancos’ well overdue contract offer and demanded a move. A switch to Chelsea made sense. The Blues had sold Shaun Wright-Phillips and were still looking for a bit of star quality in forward areas. 

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Robinho made his thoughts clear for all to see: he wanted to join Chelsea. “I want to leave, and I have got the character to tell the press that I’m not aiming to stay at Real,” he said. “It isn’t because of money, it is simply because I want to leave. My personal aim is to be the best player in the world and that isn’t going to be possible at Real Madrid. I’ve played three seasons and have given everything. I think my period at Real Madrid has come to an end. I hope the directors reach an agreement with Chelsea to resolve my situation as quickly as possible.”

The feeling was mutual, and with just a few days left in the window, Chelsea confirmed that a deal was in the pipeline, saying: “Everybody expected negotiations to go close to the wire and that’s what it will do but we’re confident it will happen. There are no hitches, it’s just a lengthy process.”

Chelsea were the only team in the race for his signature, and it looked inevitable that they would. There had been no mention of Manchester City, or any other interest, and there was no reason for it. They had finished ninth in the Premier League the previous season and had qualified for the UEFA Cup on the back of finishing sixth in the Fair Play rankings. They certainly didn’t have the money for a transfer like this. Yet, suddenly they did. 

City had been bought a year earlier by former Thai prime minister Thaksin Shinawatra, who quickly formed a connection with the supporters. In his first summer in charge, he threw a party for 8,000 fans in Manchester’s Albert Square and flew out a pop star from his homeland to perform the club’s anthem, Blue Moon. 

But there was more to Shinawatra. It was alleged that during his years as Prime Minister in Thailand between 2001 and 2006, his war on drugs had led to over 2,000 extrajudicial killings. While away from his country at the 2006 UN General Assembly, a military coup was launched to oust him, and he began to take his assets abroad. Despite this, he still passed the Premier League’s less than watertight ‘fit and proper persons’ test.

Just a year after buying the club in 2007, Shinawatra had no more money to put into the club. He had been sentenced to two years in prison in his absence by a Thai court, who had also frozen his bank accounts. He hadn’t been particularly careful with club finances; they were in the mire when City went up for sale again in the summer of 2008.

A buyer was found in the ambitious Abu Dhabi United Group, heavily backed by Sheikh Mansour, who paid £150m to take control of the club. They wanted to prove their ambition immediately with a statement signing. The problem was that it was deadline day, and if this transfer was going to get done, it had to be done quickly.

Shinawatra’s CEO, Garry Cook, and right-hand man Pairoj Piempongsant went about finding which world-class player they could pick up at such short notice. On deadline day alone, City were reported to be going after Robinho, David Villa, Dimitar Berbatov and Mario Gómez. The truth was, they were going after all four. They even put in a bid for Lionel Messi, when there was a misunderstanding over Piempongsant’s accent when he said things were getting “very messy”. Safe to say, Barcelona turned it down.

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Moves for Gómez and Villa were non-starters, but fees were agreed for both Berbatov and Robinho with Tottenham and Real Madrid respectively. Berbatov had his heart set on joining Sir Alex Ferguson at Old Trafford, however, a transfer that went through with just minutes to spare in the window. 

City had Chelsea to thank for their inadvertent help in securing Robinho’s signature. The Real Madrid board were said to be unhappy with that Chelsea were already selling Robinho shirts on their website, so refused to accept their offer. That left City, and their newfound wealth, to complete a £32.5m move for the Brazilian, making him the most expensive player in English football history. 

The move appeared to have come as a surprise to even the man himself. In his first interview, he said: “On the last day, Chelsea made a great proposal and I accepted.” It took the reporter to have to remind him that he had actually signed for another team wearing blue. The move went through so quickly that he hadn’t had a medical, and it was reported that he didn’t fully understand the terms of the contract he was signing. 

Inevitably his debut came against the team he came so close to joining, as Chelsea visited Manchester a fortnight later. Within 15 minutes, he’d shown his new team what they’d bought, and Chelsea what they’d missed out on, curling a free-kick beyond Petr Čech. It was the visitors who had the last laugh, though, coming away with a somewhat comfortable 3-1 win. 

Despite some inconsistent performances from his side during the opening months of the season, Robinho appeared to have settled into English football nicely. He scored his first Premier League hat-trick against Stoke in just his fifth league game, and had 12 goals to his name in all competitions by the turn of the year.

However, inconsistencies had started to sneak into his game again, and he went 17 games without scoring in the second half of the season. He added three goals in the final five games, taking him to 14 in the Premier League for the season, the fourth-most in the division, but there was still the feeling that his talent was worthy of more.

But all was not well behind the scenes. Robinho’s poor run of the form came following an unsanctioned trip back home to Brazil after manager Mark Hughes denied him permission to travel. The 2009 summer signings of Emmanuel Adebayor and Carlos Tevez added more star quality to the squad, but Robinho still felt like the big fish in a small pond. 

Injury saw him miss three months at the start of the next season, and not long after his return, it was all change. A poor run of results spelt the end for Hughes, and he was promptly replaced by a man worthy of the owners’ ambitions: Roberto Mancini.

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The Italian was a hard taskmaster, and Robinho’s languid, often lazy approach didn’t suit Mancini’s style. It wasn’t appreciated much in the dressing room either, with the winger also getting into an altercation with teammate Craig Bellamy. 

He started just six times in the Premier League during the 2009/10 season, and suffered the ignominy of being a substituted-substitute in the defeat to Everton. Robinho had seen enough, and he didn’t appear for City in the Premier League again, returning to Santos on loan for the rest of the season.

The added game time back in his home country earned him a spot in Brazil’s 2010 World Cup squad, where he played in four of their five games before being knocked out by the Netherlands in the quarter-finals. A return to City was never on the cards after that and, despite a brief spell back training with the club, he was quickly on the move again.

Having turned down a switch to Turkey, he joined AC Milan, with City cutting their losses by agreeing a fee of £15m. By now, he should have been at the peak of his career, but the hope of the second coming of Pelé had long since passed, and his career was taking a familiar path.

A promising first season was followed by poor form, and he was plagued once more by off-field issues, with reports of late-night parties before matches.

After three and a half years of flattering to deceive in Italy, he was back at Santos again, this time on an 18-month loan. When that spell was up, it was back to the career of a journeyman. Six months in China was followed by another two in Brazil, this time with Atlético Mineiro, before three years in Turkey spread between Sivasspor and İstanbul Başakşehir. 

Things took a much more serious and sinister turn off the pitch. In November 2017, Robinho was sentenced to nine years in prison by an Italian court for sexual assault. He, along with five other men, were found guilty of sexually assaulting a 22-year-old woman at a nightclub in Milan in January 2013. His sentence has been put on hold until the appeals process is complete. 

He has not found a new club since leaving Turkey at the end of the season, and it feels like we’ve seen the end of the enigma that was Robinho. It will always go down as a bit of what-if career, at least outside of Brazil. What if he had joined Chelsea instead? What if he had made the most of his talent? What if he had worked hard and adapted to Roberto Mancini’s style? Sadly, we will never know. 

By Ben Winfield @BenWinfield98