Garry Cook brought to an end a turbulent three years as Manchester City chief executive on Friday afternoon.
Once the existence of an e-mail ridiculing the words of Nedum Onuoha's cancer-stricken mother became widely known, in addition to the hurt felt at such comments, Cook was always likely to pay with his job unless he could prove he had not written them.
His departure will be lamented by those at City - and there were a lot - who felt Cook was doing a fine job masterminding the transition from middle-ranking Premier League club to the richest in the world.
However, Cook's inability to stay out of the headlines, to the extent the club's media relations executives kept him away from formal interviews, was always likely to prove his undoing.
And the personal nature of this latest indiscretion was a blow from which he could not recover. Here, we look at some of Cook's more forgettable moments.
July 2008 - The presence of Thaskin Shinawatra as owner was controversial given he was wanted in Thailand on corruption charges. Cook led the defence: "Is he a nice guy? Yes. Is he a great guy to play golf with? Yes. Has he got the finances to run a club? Yes." Shinawatra was subsequently sentenced to two years in prison, although the sentence is still to be served.
August 2008 - In outlining City's global vision, Cook ridicules City's club captain: "We need a superstar to get through that door. Richard Dunne doesn't roll off the tongue in Beijing."
January 2009 - Leads a high-profile pursuit of former world footballer of the year Kaka. When the Brazilian eventually rejects the proposed £100million transfer, Cook rages: "The player was clearly for sale. We had entered into a confidentiality agreement weeks ago but, in my personal opinion, Milan bottled it."
November 2009 - Cook is jeered at an official supporters' club function when he announces: "I would like to welcome Uwe Rosler into the Manchester United Hall of Fame."
December 2009 - Criticised for the badly handled dismissal of Mark Hughes and appointment of Mancini as his successor, the information coming into the public domain immediately before a 4-3 win over Sunderland, when Hughes had still to be told.
January 2010 - Jets to the USA to attend a supporters' function between the two legs of City's Carling Cup semi-final with Manchester United. "[City will become] without doubt the biggest and best football club in the world. Not if, but when, we are at Wembley having beaten Man United yet again." United win the second leg and claim the Wembley spot.
July 2010 - Allegedly writes down City's summer targets on a napkin and shows them to lifelong Blues fan Noel Gallagher. "I just had a big, long lunch with Garry Cook and the revelations are going to blow your mind," said Gallagher.
September 2011 - Resignation is accepted after internal inquiry confirms there is substance Dr Anthonia Onuoha's allegations that she was sent an e-mail, allegedly from Cook, ridiculing her own reference to a fight against cancer. The club apologises for any distress caused.