[4] In March 1998, Shepherd and Douglas Hall were the target of a News of the World exposé, led by the "Fake Sheikh" Mazher Mahmood.
The pair, believing Mahmood to be a wealthy Arab prince trying to set up a business deal, were caught mocking the club's own supporters for spending extortionate amounts of money on merchandise, calling female supporters "dogs", and mocking star striker Alan Shearer by calling him the "Mary Poppins of football", all while frequenting a brothel.
Amidst heavy media coverage, the Newcastle Independent Supporters Association and the then Minister for Sport, Tony Banks, called for the resignation of the pair.
[5] Although reports from sources close to Shepherd initially indicated he was contractually unable to resign, he and Hall had both left their posts within two weeks of the scandal breaking.
[10] Shepherd said that sacking Robson was "the hardest thing I have ever done in my life", adding "I didn’t want to be known as the man who shot Bambi.
"[11] In his 2005 autobiography Sir Bobby Robson provided detailed criticism of Shepherd's chairmanship, claiming that while manager he was denied information regarding the players' contracts and transfer negotiations.
He also criticised Shepherd and Douglas Hall, the club's deputy chairman, for their focus only on the first team and St James' Park, causing them to neglect less glamorous, although equally important, areas such as the training ground, youth development and talent scouts.
[14] On 11 May 2007, Shepherd was filmed joking with friend and Geordie con artist Steve MacNeish through his car window, stating that Owen himself was not the problem and that his advisers were the ones causing upheaval.
[19] Shepherd had been suffering from poor health over the previous six months, resulting in hospitalisation due to pneumonia and a collapsed lung, he was being treated at the time the Hall family publicly announced the sale of their shares to Ashley.
[21] On 1 November 2010, reports circulated that Shepherd was planning on making an offer for the club and returning to Newcastle as owner three years after selling it.