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Ashley, who owns the £4 billion Sports Direct empire and Newcastle United, has already lost two of his right hand men. James Easdale left last week and Derek Somners resigned today.
Now all eyes turn to Derek Llambias and Barry Leach.
Llambias was the managing director of Newcastle United until his appointment as CEO of Rangers in December. Leach is the head of brands at Sports Direct as well as Rangers' finance director now.
Considering what has happened with Somners and Easdale, it is unsurprising that reports from the Daily Mail and Daily Record claim Llambias and Leach are set to leave by the end of the week.
A well-placed source close to Rangers told Business Insider that there was no indication that Llambias and Leach would leave before the Extraordinary General Meeting on 6 March. (But, of course, that doesn't mean that they won't leave afterwards).
Rangers' representatives declined to comment on the report.
A leaked email in December last year showed Somners' fear of himself and Easdale being ousted, if Ashley didn't takeover the beleaguered football group. The email turned out to be prophetic and both are now gone.
"I am a non-confrontational man and have always tried to bring harmony to boardrooms and with stakeholders. At the risk of antagonising my army of critics I would point out that Rangers managed to pay its bills and avoid going under during my tenure," said Somners in a regulatory statement today. "These critics might not agree with how we achieved this. I look forward to alternative solutions from whoever is running the club in the future."
However, Ashley faces losing his last two lieutenants in his dwindling army at Rangers by the end of the week, when the board gathers for the EGM.
The Rangers Support Trust (RST) and major shareholder David King are now setting their sights on sacking Derek Llambias and Barry Leach. Former Rangers director and major shareholder, Dave King, is hoping to replace them with himself, Paul Murray and John Gilligan.
Meanwhile, RST also posted the following statement (emphasis ours):
"We are delighted that David Somers has finally resigned as chairman of Rangers. We note that his parting comments are entirely in keeping with his behaviour during his time at the club. His lack of ambition or ability, rampant self interest, contempt for shareholders and fans, and disastrous dearth of understanding of the position of responsibility he held will be his legacy. He will be remembered as one of the most inept and embarrassing chairmen of our wonderful sporting institution.
"Our focus now turns to the remaining directors. They should do the right thing, appoint the nominee directors and then follow Mr Somers out of the door.
"Mr Leach should have resigned when he made disparaging comments about major shareholders in a meeting with fans. This amounted to gross misconduct in our opinion and in any normally operating business he would no longer be in position. He should be suspended and subject to disciplinary procedures after the general meeting.
"Mr Llambias has serious questions to answer over the recruitment process which saw him appointed as Chief Executive. Not least whether the inaccurate information which appeared in his bio on the Rangers website, and was circulated to shareholders, formed part of the information relied on to support his application. His ham fisted attempt to use legal threats to silence legitimate criticism from the outgoing Fan Board has further alienated supporters. Taken together we believe these make his position untenable. He should also be suspended and subject to disciplinary procedures after the general meeting.
"There is a huge rebuilding process required at the club. We ask the remaining directors to leave now so it can start a few days early."
Ashley only owns 9% of Rangers (4% personally and 5% through his MASH holdings company) but that still makes him the second-largest shareholder in the group.
His attempt to boost his stake in Rangers to around 30% was thwarted in December last year by the Scottish Football Association. It cited a "conflict of interest" with his Newcastle ownership (the two clubs compete for player contracts and could in theory face each other in European competition).
However, his loans to Rangers actually gives him a lot of control, including appointing directors and bosses to the beleaguered football club. This is something the fans hate.
In the same month, Ashley nominated his right-hand men, Llambias and Leach, to Rangers' board.
Lambias is hated by the Rangers fans. This especially came to a head when he as instructed the football club's lawyers to disband the Rangers Fan Board (RFB), cementing many fans' views over Ashley's desire to not listen to the fans.
So, considering the fate of Easdale and Somners, it's looking like a 'when', not an 'if', for Llambias and Leach leaving the Rangers board and Ashley out in the cold.