The Prime Minister had wanted to keep Justine Greening in her top team, but failed to stop her quitting with the former education secretary rejecting a transfer to another department.
Ms May’s authority was further called into question after Health Secretary Jeremy Hunt not only rebutted an attempt to move him, but managed to secure an enhanced role in his current post.
One senior Conservative MP said: “If this was meant to show she has the power to reshuffle her Cabinet, it has shown the complete opposite.”
Changes made to the set up at Conservative HQ were at least well received, with new Party Chairman Brandon Lewis and his deputy James Cleverly expected to have a positive impact on the Tories’ campaign machinery.
But the day started with a botched statement, naming the wrong person being given a top job, and was then characterised by a series of announcements confirming Ms May would allow people to keep posts.
The Prime Minister had already conceded there would be no move for her most senior ministers – Foreign Secretary Boris Johnson, Chancellor Philip Hammond, Home Secretary Amber Rudd and Brexit Secretary David Davis – despite talk last year that some might be transferred or sacked.
But she did want to shift Ms Greening and Business Secretary Greg Clark, both who had been criticised by her allies, and also Mr Hunt.
Ms Greening left Downing Street around 8pm on Monday night after a gruelling three-hour meeting in which she rebuffed attempts by Ms May to make her stay at the Cabinet table.
The Prime Minister had wanted to move her from the Department for Education for some time, with Ms May’s allies claiming the former minister was disloyal and had not fully embraced the spirit of the PM’s desired reforms.
But Downing Street also wanted to avoid the instability of a long-serving minister quitting and heading to the backbenches, where she is now free to join forces with rebels who like her voted to stay in the European Union.
The plan was to offer her a job at the Department for Work and Pensions, but Ms Greening refused and had already made her intentions clear days before as she started tweeting about her achievements at the DfE.
Aides said Ms May was “disappointed”, but respected Ms Greening’s decision to leave. Damian Hinds will replace her as the new Education Secretary.
Ms Greening said on Twitter: “I’ll continue to do everything I can to create a country that has equality of opportunity for young people & I’ll keep working hard as MP for Putney.”
Mr Hunt also refused a move proposed to him and instead argued he stay in post at the Department of Health to fully merge the NHS and social care.
One party source told The Independent: “It is apparently just possible that Jeremy Hunt was speaking the truth when he said that the health job was the last one big job he would do in politics.
“It seems that was his intention, and he didn’t feel leaving during the winter pressures on the NHS in particular was the right thing.”
Mr Hunt apparently argued his case for staying so “passionately”, that he now takes responsibility for the drive to reform the NHS, gaining a new job title – Health and Social Care Secretary – and departmental name to reflect the enormity of the job ahead.
Sajid Javid will also head a department with new name, the Ministry for Housing, Communities and Local Government, in an attempt to underline Ms May’s commitment to tackling the housing shortage.
In both cases officials said the costs of changing stationary, signs, business cards and branding for the newly named departments would be kept to a minimum.
Ms May had planned to move Mr Hunt to the Department for Business, where critics claimed Mr Clark had failed to live up to the job.
But after being kept waiting at Downing Street, Mr Clark was told he would keep his post and will now push through Ms May’s pledge to cap energy bills.
Another minister Ms May is said to have wanted moved, Andrea Leadsom, will also keep her job as Leader of the Commons.
“It’s meant to be about the Prime Minister asserting her power, but it’s served to underline her weakness.”
Another MP said it would not inspire people to think the Government had “renewed vision”, adding: “There’s not very much there which is meaty.”
The Work and Pensions post was eventually taken by Esther McVey who wins her first Cabinet post, with the former holder of that role David Gauke going to the Ministry of Justice.
Ex-Justice Secretary David Liddington moved to the Cabinet Office to take up responsibilities left by Damian Green, who quit last year following an investigation into breaches of the ministerial code.
Mr Liddington will deputise for Ms May at Prime Minister’s Questions and chair critical Cabinet committees, including those on Brexit, but will not receive the prestigious First Secretary title Mr Green had.
The day started badly when Conservative HQ announced on social media that Chris Grayling would be the new party Chair, only for the message to be deleted moments later.
That job went to Mr Lewis, who with his deputy Mr Cleverly, will head a team of party vice-chairs designed to bring on new talent and show a fresher more diverse face to the Tories.
James Brokenshire resigned from his Northern Ireland secretary job on grounds of ill health, weeks before major surgery for a lesion on his right lung, and was replaced by Karen Bradley.
Her old slot was filled by Matt Hancock, who was promoted to be the new Culture Secretary.
Others who remained in post included Liam Fox at International Trade, Michael Gove at the Department for Environment, Food and Rural Affairs, Mr Grayling as Transport Secretary and Penny Mordaunt at International Development.
David Mundell stays on as Scottish Secretary and Alun Cairns as Welsh Secretary, while Jeremy Wright keeps his job as Attorney General.
Defence Secretary Gavin Williamson and Chief Whip Julian Smith keep their roles having only recently been appointed.