During his time at Newcastle, both as an active assistant to and later replacement of Sir John Hall as chairman for ten years, Shepherd proved an often outspoken and controversial figure, even at times alienating his fellow passionate supporters.
The brothers often worked with Sir John Hall, who owned the property development business Cameron Hall Developments, and had become a key share holder in Newcastle United. After Hall's vision of building Newcastle into a sporting club along the lines of AS Roma or FC Barcelona, he looked to consolidate the operations of Newcastle United. Shepherd Offshore had started to build a holding in Newcastle United, and so Shepherd became involved in the football business, alongside Hall's son Douglas Hall.
In 1996, Shepherd was tasked by Hall to bring Alan Shearer to the club, which he did for a then world record fee. The confidence Shepherd showed in completing the deal persuaded Hall, who wanted to retire to Spain, to effectively offload the day-to-day running of the club to Shepherd as chairman, and his son Douglas as the active Hall family member on the board. Shepherd agreed with his brother Bruce to take the position, while Bruce continued to run Shepherd Offshore.
Amidst heavy media coverage, the Newcastle Independent Supporters Association and the then Minister for Sport, Tony Banks, called for the resignation of the pair. 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.
His general approach to running the club, as well as the ongoing fallout from the News of the World story, earned Shepherd a number of unflattering nicknames such as "Fatty Shepherd"
,the "Fat Controller"
and "Baron Greenback"
Only ten months after resigning, Shepherd and Hall, the majority shareholders at Newcastle, voted themselves back on to the board. This led to the immediate resignation of the PLC chairman David Cassidy, who had taken the position just six months earlier. Shepherd then went on to take over as PLC chairman.
It is unclear if Shepherd made his statement after consulting Robson, but Robson admits that he had an agreement with the club that he would retire at the end of the season. Robson also stresses that there was an agreement that he would not be sacked. Afterwards, Shepherd said that sacking Robson was “the hardest thing I have ever done in my life”, but then added “I didn’t want to be known as the man who shot Bambi..
In his 2005 autobiography Sir Bobby Robson provides 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. The club's training ground has been notorious in the past, due to its unkempt state, for causing injuries to first team players.
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. The video was later published on the Youtube site.
This followed numerous previous bid negotiations from which nothing had materialised. Under Stock Exchange rules Ashley then had to submit an offer for the remaining shares. Should he go over 50%, Shepherd would no longer be in control of the club and Ashley would be able to replace the board..Shepherd initially came out fighting, but later agreed to meet with Ashley and the board on May 29. On 7 June 2007, Shepherd agreed to sell his shareholding to Ashley.
However, Shepherd had been suffering health difficulties for the previous six months, resulting in hospitalisation through pneumonia and a collapsed lung, which he was being treated for at the time the Hall family publicly announced the sale of their shares to Ashley. On 24 July 2007, it was announced that Shepherd was stepping down with immediate effect, to be replaced by deputy chairman Chris Mort.