Cook needs to meet chairman Khaldoon Al Mubarak's targets © Getty Images

Having failed to clinch a deal for Kaka in January 2009, Manchester City chief executive Garry Cook claimed AC Milan “bottled it”.

"He clearly was for sale but we never got to meet with the player,” Cook said at the time. “The behaviour of AC Milan got in the way."

It was a curious remark. City’s £100 million deal for Kaka was understandable for an ambitious, mega-rich club looking to reach parity with the big four, but it was always unlikely. For one thing, Brazilians rarely seem keen to move to England for whatever reason and Kaka, like Cristiano Ronaldo, had long seemed destined for a move to Real Madrid.

Cook, who arrived after 12 years with sportswear giant Nike, confirmed he had tried to negotiate with Kaka’s father on setting up humanitarian projects for the player, but said “financial demands came to the fore”. The suspicion then, as it is now, was that Cook hadn’t quite come to terms with the fact that City remain a work in progress on the field.

The point was brought home once more last month when Santos youngster Paulo Henrique Gansu suggested he was unhappy about City potentially getting first option on his signature as part of the Robinho loan. "I don't want to play for Manchester City,” he said. “I'd prefer to play for a big club in Europe such as Milan, Real Madrid or Barcelona." For Cook to insult Milan seemed naive to say the least and eyebrows have been raised ever since.

Reports have emerged in the national press that Cook’s position at City is under scrutiny. The Milan remark was not Cook’s only PR error. He had previously claimed former owner Thaksin Shinawatra - the former Thai PM accused of, among other things, corruption, tax evasion and authoritarianism - was “a great guy to play golf with” (perhaps Kaka’s father had been less than convinced about the motive behind the proposed humanitarian projects). More recently, the sacking of Mark Hughes in December was justifiable but its handling was wretched, and Cook attracted plenty more criticism after his explanation as to when exactly Roberto Mancini had been offered the post.

While trying to help City become “the biggest and best football club in the world”, Cook was last month helping Mancini strengthen in defensive midfield. Real Madrid’s Fernando Gago was the big target but, after early negotiations showed few signs of progress, they turned to Parma’s Kenya international McDonald Mariga. The move, according to Kenya PM Raila Odinga, fell through as City did not leave enough time to force through a work permit.

When it emerged that Mariga would not arrive, City went back in for Gago. However, as Real Madrid director general Jorge Valdano revealed this week, the bid was made so late in the day that there was no conceivable hope of the move being concluded. "They had nothing prepared, not even one document signed," he told El Pais. "They had not reached an agreement with the player and they would have had to have done everything in 40 minutes."

Some of the criticism that has come Cook’s way may well have been unfair and it is likely that many of the situations involved more complexities than we have been privy to, but the regularity of the avoidable bad press is alarming and it is hard to imagine that City’s owners are content. The club’s public image is souring and, unlike Peter Kenyon's time at Chelsea, targets have not been secured. If City are to become the biggest and best football club in the world, they may well be looking at someone with a background in the sport to help take them there.