One of the government officials caught up in the Partygate scandal which engulfed Boris Johnson’s premiership is playing a key role in negotiating the future of The Daily Telegraph.
Sky News can reveal that former deputy cabinet secretary Helen MacNamara is among the advisors to RedBird IMI, the Abu Dhabi-backed vehicle whose acquisition of the broadsheet newspaper has effectively been blocked by the government in recent weeks.
Ms MacNamara, who was among those given fixed-penalty notices by police for attending lockdown parties in Downing Street during the COVID-19 pandemic, is working at Robey Warshaw, which is acting for RedBird IMI on its options for the onward sale of the media assets.
Her role at Robey Warshaw, where George Osborne, the former chancellor, is a partner, has not previously been disclosed, but sources close to the Telegraph process confirmed that she was actively involved in the discussions.
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Robey Warshaw has become one of the City's most successful merger and takeover advisers since it was established by Sir Simon Robey, widely regarded as the most successful British investment banker of his generation.
Ms MacNamara was a highly regarded government official before leaving Whitehall in February 2021.
Among her roles, she served for more than a decade at the Department for Culture, Media and Sport - the same ministry responsible for ruling on the fate of The Daily Telegraph as RedBird IMI negotiates over the structure of an auction expected to kick off within weeks.
Her reputation was, however, tainted by last year's report by Sue Gray - a senior civil servant at the Cabinet Office who is now a key member of Sir Keir Starmer's team - which concluded that Ms MacNamara had brought a karaoke machine to a leaving party which was prohibited under social distancing rules at the time.
During the Covid inquiry, it emerged that she had been the subject of misogynistic messages sent by Dominic Cummings, Mr Johnson's top aide, to the then prime minister.
After leaving the civil service, Ms McNamara joined the Premier League, where she ran its policy and corporate affairs functions before stepping down after just two years.
She is understood to have been working at Robey Warshaw for several months.
Ms MacNamara is no longer bound by restrictions imposed by Whitehall's Advisory Committee on Business Appointments.
Her involvement in the Telegraph process adds to the number of politically connected figures who are embedded in talks about the fate of the traditionally Conservative-supporting newspaper.
As well as Mr Osborne, that list includes Nadhim Zahawi, the former chancellor, who has been advising the Telegraph's long-standing owners, the Barclay family.
Sky News revealed earlier this month that RedBird IMI and the DCMS were discussing amendments to the statutory instrument which dictates various elements of the Telegraph's governance during the period in which the Abu Dhabi-backed vehicle holds a call option that was supposed to convert into ownership of the Telegraph and Spectator magazine.
An announcement about a workable structure could be made in the coming days, the Financial Times reported last week.
RedBird IMI is understood to believe that The Spectator could be worth £100m or more as a 'trophy asset' but that that valuation would be impaired if the magazine is sold in the same transaction as the newspapers.
Earlier this month, Sky News revealed that Raine Group, best-known in Britain for its roles in recent deals involving Manchester United and Chelsea football clubs, and Robey Warshaw were being lined up to advise on the next phase of the Telegraph's ownership.
RedBird IMI, which is part-owned by US-based RedBird and majority-owned by Abu Dhabi's IMI - which is backed by the UAE's deputy prime minister and ultimate owner of Manchester City Football Club, Sheikh Mansour bin Zayed Al Nahyan - had argued that fears about its ownership of the Telegraph were unfounded.
The deal faced vehement opposition from Telegraph journalists and Conservative politicians from both houses of parliament.
RedBird IMI had sought to defuse controversy over the deal by offering legally binding assurances over editorial freedom, and in January restructured its bid to incorporate a new UK holding company which would own the Telegraph titles and Spectator magazine.
The takeover was rendered impossible, however, by the government's adoption of legislative changes to prevent any ownership of British national newspapers by investors connected to foreign states.
Lucy Frazer, the culture secretary, has said she is minded to refer the RedBird IMI takeover of the Telegraph titles to an in-depth inquiry by the Competition and Markets Authority.
The fate of the Telegraph has been up in the air for almost a year after Lloyds Banking Group seized control of its parent companies after the Barclays fell behind on debt repayments.
Since then, a number of bidders including the Daily Mail proprietor Lord Rothermere and the GB News shareholder Sir Paul Marshall have shown an interest in buying the titles.
Sky News revealed this month that Sir Paul was stepping down from the board of the parent company of GB News, the television news channel he has helped to bankroll, as he prepares a fresh bid for the Telegraph.
A trio of independent directors of the Telegraph's holding company were parachuted in by Lloyds Banking Group last year after the lender seized control of the newspapers from their long-standing owners, the Barclay family.
However, the sale process was pre-empted by RedBird IMI repaying £1.16bn of loans owed by the Barclays to Lloyds, with £600m used to purchase the call option and the remainder as a loan secured against other family assets, including the online retailer Very Group.
Earlier this year, the independent directors appointed to oversee the sale of The Daily Telegraph were warned by Ms Frazer that the removal of the newspaper's two most senior executives breached a government order - and that any subsequent transgression could result in a multimillion pound fine.
RedBird IMI, Robey Warshaw and the DCMS declined to comment.
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