There was an interesting piece in The Independent, which lifts a lid a little on some of the complexities behind the deal, and perhaps (from our standpoint at least) why the deal failed:
However, not so clear cut according to reports in the Italian press today, via this piece from The Mail:
Cook's six-man delegation, including lawyers with expertise in intellectual property rights, had headed to Italy with high hopes. They knew they needed to sell their image rights ideas to Leite before they would manage to meet and convince Kaka himself. But that seemed unlikely from the moment they sat down. Attempting to establish whether Kaka's current deal with Adidas left any room for City to tie up image rights deals of their own and earn a return on their £91m investment, the club met a wall of resistance from Leite.
City told Leite of their ideas for a Kaka Foundation, through which his image would make money for a "humanitarian" cause. There was talk of lucrative digital TV and internet image rights deals. Privately, City were astonished that Kaka's current entire image rights income is believed to be €8m (£7.4m). In Cook's previous role with Nike, he was responsible for the international image rights of the basketball player Michael Jordan. They earn him $12m (£8.6m) a year for his signature alone. Football clubs have not touched the surface of such commercial opportunities.
But Leite would only talk about the player's personal terms. "They didn't want to get to the complexities and the sophistication," Cook said. "They just wanted an offer in cash terms." A brooding presence as the talks foundered was Galliani, in a side room nearby.
Getting nowhere as Monday night drew on, City suggested a period of reflection and shook on a plan to meet again in Milan today. Leite's desperation for a quick deal then led City to agree to bring that date forward 24 hours. A new day, they seem to have figured, offered hope of a change of heart. But after Cook and his delegation had left, the Italians decided they could not wait – and run the risk of City embarrassing them by unilaterally calling talks off. Cook was in the departure lounge of Milan's Linate Airport At 11.03pm, Italian time, when he received a phone call from Alberto Zilani, Leite's translator. "We want a cash offer now," Zilani said. Resigned to the fact that the deal was going nowhere, Cook called it off and both clubs formally announced the fact.
The one worry I had with the fall out from the aborted deal, was how this would affect our ability to sign players of a similar standing to Kaka in the future.
'The truth is that in six hours of talks with Manchester City they only asked questions and didn't make an offer for Kaka.
'How on earth did they think they were going to buy him? It's one thing buying a property or a company but completely another when you are trying to charm one of the best players in the world.'
Gazzetta revealed that the negotiations had taken place in the law offices of Milan firm Izzi-Tognazzi and were stop start as City were constantly ''asking for time outs.''
Gazzetta said that Kaka's agent Bosco was getting fed up at the fact that City's Gary Cook and Simon Pierce were just asking questions primarily on the player's image rights.
Gazzetta also claimed that at 10pm on Monday night City, after ''consulting with the shaikh said they would make an offer via email the following day.''
Gazette wrote: ''At that point Bosco and AC Milan vice president Adriano Galliani looked at each other and asked to call off the talks. Cook tried to change direction but it was too late as Galliani had already called Silvio Berlusconi.'
The worry is that Cook's stinging remarks yesterday could turn out to be ill advised, given that surely Milan and Kaka's words are likely to hold more weight in the footballing world than Cook's argument that Milan were 'bottlers'.
Perhaps it would have been far wiser to have bitten his tongue and simply thanked Milan and Kaka for their interest and time during the negotiations, rather than to come across as a slightly inexperienced and naive negotiator with little idea of how to conclude a high profile transfer?