During his time at the club, he offended Nedum Onuoha's mother, lambasted AC Milan while also brokering the deal that brought Abu Dhabi United Group to the club
Former Manchester City chief executive Garry Cook has confessed that he looks back on his gaffe-prone time at the club with a measure of regret, stating that he embarrassed the club's fans.
He arrived at the club in 2008, from Nike, and remained for three years before an internal investigation was launched by the club into an email Nedum Onuoha's cancer-stricken mother received mocking her illness.
Cook maintaining that his email had been hacked into, before eventually resigning over the matter.
"I'm also a great believer that if you're not making mistakes, you're not trying hard enough" - Garry Cook
"There are no excuses. There are my interpretations and there are the interpretations of the press," Cook told BBC Radio Manchester.
"The thing I always felt when those interpretations were manifested was the embarrassment I'd caused the fans.
"In the end, I really felt that I didn't want to continue being the scapegoat of Manchester City and the point of attack.
"I am who I am but I was getting more and more concerned that it was becoming more about me than it was about the football club and the fans.
"That's not fair to them, it's their club and they deserve better than that."
Cook famously claimed that AC Milan had “bottled it” over a proposed transfer of Kaka in, while he also introduced Uwe Rosler into the Manchester City Hall of Fame by mistakenly naming bitter rivals Manchester United instead at the ceremony, two mistakes that he does not look back on with fondly.
"I was angry at AC Milan for the way they treated the football club with regards to Kaká," he added.
"In retrospect, it was disrespectful to make public statements the way I did and I obviously regret that.
"Making a mistake with Uwe Rösler, my biggest concern was if I had dishonoured Uwe Rösler or the supporters' club.
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"I deeply regret making a mistake. But I'm also a great believer that if you're not making mistakes, you're not trying hard enough."
Despite those controversial incidents, though, Cook also made a huge and lasting impact during his time at the club by negotiating the deal which brought the Abu Dhabi United Group to City.
After some heavy investment both on and off the pitch, Manchester City went on to clinch their first league title since 1968 last season.
"I am proud of what I've done, but it's not me alone. What I feel I managed to do was build a team of people who believed and could see the vision," he said.