O.J Simpson and Hertz – 1992


Before he became famous for all the wrong reasons. O.J Simpson, the former NFL football star was the face of Hertz rental cars. He fronted a series of commercials for the car rental corporation throughout the 1970s alongside other celebs including Jamie Lee Curtis. The deal – worth a reported $550,000 (£343,526) a year – came to abrupt end in 1992 when reports first surfaced of domestic abuse between Simpson and his former wife Nicole Brown Simpson. Two years later, the athlete was arrested – and eventually found not guilty by criminal court jury – for the murder of his ex wife and her friend Ronald Goldman.

John Terry and Umbro – 2012

Umbro is ending its long-running ties with the former England captain.

The sportswear brand announced its decision not to renew its deal with the former England captain last month following allegations he racially abused Anton Ferdinand during a match against Queens Park Rangers last season. It was not the first time the football player’s future with Umbro has come under scrutiny. In 2010 it was revealed that he had a four month affair with his then team-mate Wayne Bridge’s then-girlfriend Vanessa Perroncel, prompting speculation about his tie-up with the brand. Terry has been the face of Umbro since 2002, in a deal worth a reported £4m, however on-going off-the-field transgressions meant the company felt the time was right to distance itself from the defender.

Michael Phelps and AT&T and Rosetta Stone – 2009

The 22-time Olympic Gold medallist came under fire after a picture surfaced online showing him smoking cannabis at a party in Southern California in 2009. In response, AT&T and Rosetta Stone decided not to extend their deals at the end of the year. Kellogg followed soon after and cancelled its sponsorship, worth a reported $500,000 (£312,325), saying the athlete’s image was no longer “consistent with the image of Kellogg.” Sandwich chain Subway, however stuck by Phelps, even going so far as to have him front an advert title ‘Be Yourself.’

Jerry Seinfeld and Microsoft – 2008

The software giant roped in comedian Jerry Seinfeld to spearhead its ad battle against Apple in 2008. The comedian starred with Microsoft’s co-founder in a baffling TV spot that showed the two discussing shoes before the billionaire philanthropist shakes his behind as he walks across a car park. The campaign, which cost a reported $300m (£187m) was meant to herald a new dawn for the company and its trouble Windows Vista operating system. The ads were pulled after a wave of public backlash forced the business to rethink its advertising strategy.

Hulk Hogan Ultimate Grill – 2008

George Foreman’s Lean, Mean, Fat-reducing Grilling Machine was one of the most successful celebrity endorsements ever, but Hulk Hogan failed to have the same impact for Ultimate Grill, which launched in 2008. The indoor grill failed to reach the success of Foreman’s effort, not least because it had a habit of setting fire to cooking oil sprays when heating up, which caused a product recall.