#1 Ricardo Kaka (from AC Milan)
Upon achieving disappointing results from the stunning signing of Robinho from Real Madrid, Manchester City laid their eyes on another Brazilian to head their quest for revolutionizing English football. Kaka was at the peak of his powers back in those days, and any transfer involving the midfielder would have to be a big one. However, Manchester City left everyone struggling to find adjectives to describe their pursuit of the 'man who belongs to Jesus'.
City allegedly put on the table, for Kaka, what many analysts call 'the biggest offer in the history of football'. The exact numbers were never revealed, but it is believed to have been a £500,000 per week contract for the Ballon d'Or winner, which would have made him the highest paid athlete in the world back then.
Though it doesn't sound so today, it was unthinkable a decade ago. On top of that, City had reportedly offered £100 million to AC Milan for their lovable icon.
The transfer never really happened, although everyone involved in the negotiations had green-lighted the move - starting from the City hierarchy to the AC Milan board and even Kaka's father.
Unfortunately, the one person who was against the move was Kaka himself. He recently revealed the same and explained how he was unsure of committing to a long-term project like that of City's. The man who headed the great pursuit - former City chief Garry Cook - also later disclosed that Kaka regrets snubbing English football.
Kaka's career went downhill since that eventful January of 2009, and he eventually left Italy for Real Madrid. He was never the same player again, and City would be glad that their super-plan did not work.
Also read: Manchester City: Weekly Wages of First-Team Stars Revealed
They invested the supposed £100 million on players like Carlos Tevez, Yaya Toure and David Silva over the next two seasons instead - all three of whom turned out to be huge hits. Nonetheless, it was a simply unbelievable transfer that Manchester City missed out on. Just a step away from real-life Fantasy Football...