Former Downing Street head of strategic comms Mark Flanagan told PRWeek: ‘The feeling inside Number 10 is he underestimated media interest in him as an individual; he's been unlucky with a few issues and some elements of the lobby are resentful of his TV background.’
However, Flanagan – who now works at Portland PR as partner for digital comms - claimed Oliver was not being blamed internally for the media handling of the Prince Andrew story.
Oliver was reported to have briefed the BBC that Prince Andrew's position might become ‘untenable’ if further revelations about his links to Epstein come to light. It has been reported that he later backtracked on this statement.
Oliver also drew mocking media coverage on Monday for failing to arrive at Downing Street in time to join David Cameron’s motorcade on the way to a meeting of the Cabinet in Derby.
Since joining Downing Street, Oliver is understood to have introduced new comms strategy meetings that look beyond the coming week, which have gained a positive response from the civil service.
Oliver joined Downing Street on 28 February, and sparked media interest in his attire, including Dr Dre-designed headphones – prompting Daily Telegraph deputy editor Benedict Brogan to dub him ‘Craig Dre’.
Flanagan added: ‘For my part, I think he's a talented and intelligent guy who will make it work but needs to avoid getting bogged down in the tactical. It’s ridiculous for elements in the lobby to write him off at this stage.’
A public affairs source with links to Downing Street who refused to be named has suggested that Oliver has ‘struggled to find his feet’.
‘The pace of life at Number 10 is frenetic, whilst the BBC proceeds at a very leisurely pace,’ added the source.