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The £100million price tag gets thrown around for fun these days: Declan Rice and Jack Grealish have both had it slapped on their head in recent weeks.

But back in 2009, when Manchester City tried and failed to sign AC Milan and Brazil superstar Kaka, it was more than double the world record transfer fee.

 'Break the bank' doesn't even come close to what City were willing to spend on Kaka
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'Break the bank' doesn't even come close to what City were willing to spend on KakaCredit: Getty Images - Getty

A dramatic takeover from the Abu Dhabi Group and Sheikh Mansour on the final day of the 2008 summer window proved to be a critical moment in the history of the Citizens.

Not only did they instantly become football’s richest club – that was merely the beginning – they also managed to see off competition from Chelsea to sign Robinho from Real Madrid in a deadline day £32.5million move.

As the season passed the midway point, City sharpened their focus on bringing in further talent to boost what looked to be an average season under Mark Hughes.

Occupying 11th place, the chance to take advantage of a full transfer window for the first time under new ownership presented itself, and so the pursuit of Kaka began.

 Man City were in desperate need of some inspiration
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Man City were in desperate need of some inspirationCredit: Getty Images - Getty

Preparing for AC Milan’s trip to Portsmouth in a UEFA Cup knockout tie, Kaka admitted that he had spoken with close friends Robinho and Elano about a move to Manchester City.

Club representatives made initial contact with the Brazilian’s entourage as the groundwork was laid for further negotiations in the upcoming winter window.

City’s chief executive, Garry Cook, and a collection of club officials travelled to Italy to propose the idea of a move. No price was agreed, but an unspoken arrangement was reached between the two clubs.

Kaka’s agent confirmed an offer had been submitted by City for his client, but Kaka himself played down the chances of a move, saying he ‘wished to grow old’ in Milan.

 Garry Cook was sent by Man City with a blank cheque to forge a deal
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Garry Cook was sent by Man City with a blank cheque to forge a dealCredit: Getty Images - Getty

But it soon became apparent that the Brazilian’s personal preferences were not the only thing to consider. In light of the economic downturn, Milan – while loathe to potentially lose one of their top talents – allowed Kaka to speak to City about a move, as the prospect of the glamour transfer coming to fruition, suddenly became a reality.

The momentum was building firmly in City’s favour of pulling off a transfer that was set to double the previous world record of £46million – set by Zinedine Zidane in 2001.

With Milan’s hierarchy paving an exit-route for their star player, the club’s support took it upon themselves to dissuade both the player and chairman to resist the money on offer.

Fans staged protests at the San Siro during Milan’s win over Fiorentina, displaying banners with messages of 'Kaka is priceless' and 'Hands off Kaka'.

 Milan fans would not let Kaka leave
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Milan fans would not let Kaka leaveCredit: AFP - Getty
 Beckham even got involved to thwart his former rivals
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Beckham even got involved to thwart his former rivalsCredit: AFP - Getty

David Beckham, who was on loan with the Serie A club, optimistically declared his confidence that his teammate would stay and resist the riches of his former Manchester rivals.

Following hours spent with Kaka’s father and representative, Bosco Leite, City were becoming increasingly confident of landing their man.

Furthermore, Milan CEO Adriano Galliani was content to accept a package that would have allowed the club to erase their debts and begin a rebuilding programme to ensure the Italian giants restored themselves as one of Europe’s leading clubs.

But much to the relief of the club’s support, Kaka announced he would be staying in Milan and marked the occasion by ‘celebrating’ with family and friends in his home.

City, meanwhile, were incandescent with anger over their failure to land another marquee signing and held Milan responsible for curtailing their lavish plans.

 The fans prevailed over money in the end
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The fans prevailed over money in the endCredit: Getty Images - Getty

Cook returned from Italy with a scowl instead of his usual trademark grin as he had to explain the unexpected hitch in both his and City’s master plan.

Put simply, Cook accused the Serie A club of 'bottling it' in light of the public pressure that was applied by support and political figures.

Cook insisted that Milan wanted to sell Kaka and had even signed a confidentiality agreement as part of negotiations to eventually seal the signature of the Brazilian.

The Rossoneri star admitted he had seriously considered joining the ‘great project’ that was presented to him at City, but eventually settled on staying in a place where he enjoyed the best moments of his career.

 Maybe Kaka would've fared better than Robinho at City
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Maybe Kaka would've fared better than Robinho at CityCredit: Getty Images - Getty

In the aftermath, Brazilian teammate Robinho stormed out of his club’s winter training camp in Tenerife, which was reportedly due to being refused permission to spend his 25th birthday in his native country.

It was an episode that the club scarcely needed at a time where their status within European football was being reaffirmed. Not only was their failure to land Kaka played out in such public fashion, but their first marquee signing was seen to be challenging the authority of those in charge at City, despite having spent less than four months with the club.

Craig Bellamy, Nigel de Jong and Shay Given were ushered through the door before the winter window closed, but it did little to disguise the fact City had been shown up for the all the football world to see.

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