Then-Chelsea manager Luiz Felipe Scolari was reportedly left "fuming" having missed out on signing the Brazil international, and Robinho has revealed the Blues' impatience and poor relationship with Real caused the deal to break down, per FourFourTwo (via The Sun's Gary Carter):
My goal was to move to Chelsea—Big Phil [Scolari] said I could make the difference for him as his squad, according to him, was not creative enough.
But Real Madrid had fallen out with Chelsea—they didn’t like them selling shirts with my name on before the deal had been done.
I’m pretty sure that this error was one of the main reasons why the transfer failed, as it was a matter of pride for Real Madrid.
City broke the British transfer record to sign Robinho, and the move was met with great fanfare as it signalled the Sky Blues' increased ambition with the financial backing of their Middle East-based owners.
Then 24 years old, Robinho was an exciting prospect, but he stayed at City for just 16 months before being loaned to Brazilian club Santos and eventually moving to AC Milan.
He started well at City, netting 11 goals in his first 16 Premier League games at the club, but he cut a frustrated figure at times, accused his team-mates of having "the mentality of a small side" and went AWOL from a winter training camp in Tenerife, per the Guardian.
Per FourFourTwo (via Carter), Robinho, now 33 and playing for Brazilian side Atletico Mineiro, insisted then-City manager Mark Hughes gave him permission to return home from the Tenerife camp, which came just four months after his move to the Sky Blues:
When I arrived at City, I hadn’t had any vacation time and he promised me he'd give me one week to get some rest.
I believed what he told me so when I travelled to Tenerife, I went to him and said, "Mister, can I have my vacation now?"
He said, "OK." I packed my things, let the club know that I was leaving and enjoyed a week back home because he had allowed me to go—he had given me his word.
Having missed out on signing Robinho, Chelsea went on to win a third Premier League title in the 2009-10 season under manager Carlo Ancelotti—Scolari was sacked in February 2009 after less than a term in the job.
It took City until 2012 to win their first Premier League title after the cash injection from Sheikh Mansour bin Zayed Al Nahyan was put to better use and Robinho had left the club.
Chelsea arguably dodged a bullet in missing out on Robinho as he never quite lived up to his potential.
But the saga that saw him move to City will always mark the start of the Sky Blues' increased clout in the transfer market and the subsequent success that has followed.