t this year’s Labour party conference, health secretary Wes Streeting opened his DJ set at one late-night party with the feminist anthem Independent Women by Destiny’s Child. It was a tribute to Rachel Reeves, who was standing nearby.

A few moments later, partygoers watched as the health secretary scurried over, a look of faux alarm on his face. “It’s the lyrics – I’m so sorry!” he gasped. The chancellor, a quizzical look on her face, joined him as he mouthed the offending words: “The shoes on my feet (I bought ’em). The clothes I’m wearing (I bought ’em) … ” They stifled horrified laughter.

The cash-for-clothes row, in which Keir Starmer, Angela Rayner and, to a lesser extent, Reeves have come under sustained fire for accepting gifts worth thousands of pounds from Labour peer Lord Waheed Alli, has been a low point for the newly elected government. It is certainly not how Starmer envisaged his first 100 days in office would end. Keen to avoid the same mistakes as Tony Blair, who later admitted he wished he had done more early on, this Labour government got off to a hyperactive start after 14 years out in the cold.

But along with all the big decisions, new legislation, foreign trips and attempts to set the political narrative, they have found themselves buffeted by headwinds: not just over donations, but also stories of internal rows at No 10 and, perhaps most significantly, a backlash over the cut to the winter fuel payment.

There are, of course, different views on how meaningful “100 days” assessments really are. Do these first weeks set the tone for government, or are they quickly forgotten? After all, any new administration takes time to get their feet under the table, especially when they have little institutional memory of power. But, for better or worse, this is a moment when the political ecosystem pauses and ponders. I spoke to more than two dozen people, including cabinet ministers, senior political aides, leading civil servants and Keir Starmer himself, to get a sense of how it has been on the inside.

When Keir Starmer walked up Downing Street just hours after Labour had won its enormous landslide victory, he grasped his wife Victoria by the hand and worked his way up the flag-waving, cheering crowd, shaking hands and hugging. The images were beamed across the world. But what nobody picked up was the fleeting moment when the new prime minister locked eyes with his two teenage children, who were tucked away in the throng.

“I can safely tell you this secret now,” he tells me. “We hid the kids in the crowd in Downing Street. I really wanted them to be there, but we didn’t want them walking down the street because of the way we’ve tried to keep them out of the public eye.

I caught their eye. I didn’t go to them, for obvious reasons. But it was fantastic to have them there. Nobody knew. But it was a really important moment for the family.”

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After Starmer’s speech to the country, the couple headed through the famous black door of No 10 to be greeted by the cabinet secretary, Simon Case. But Starmer stopped briefly to shake hands with one man: Morgan McSweeney, the political mastermind behind the party’s win. The Starmers were led into the cabinet room, where they were joined by their children, Victoria’s sister and elderly father, Bernard, for a cup of tea and a biscuit, and a brief chance to privately take in the enormity of what had just unfolded.

For his team, bone-tired from an intense 43-day election campaign, yet running on adrenaline after a night of dramatic results, their arrival in Downing Street on the morning of 5 July came as something of a shock.

“You get two or three hours sleep in a hotel, then stagger to 70 Whitehall,” one senior No 10 figure says, referring to the address of the Cabinet Office. “They give you a bacon sandwich, a coffee and a terrifying security briefing, and then you get ushered into a room to start forming a government.”

“It’s mad, it doesn’t feel safe,” another adds. “It’s an incredibly brutal system. Other countries have transition periods.” World leaders including Joe Biden, Emmanuel Macron and Olaf Scholz made the same point in their first phone calls with the new prime minister.

Labour had a plan for their early days of government, carefully worked on for months by Sue Gray, Starmer’s then chief of staff. But despite that, I hear one constant refrain: it has been far from easy. Starmer insists he expected that. “It’s proved the thesis that government is tougher, but also that government is better, because you get to take decisions.”

But after a bumpy start, there is anxiety that this might be more than the usual stumbles of a government getting used to the vagaries of office, and instead the symptoms of a dysfunctional No 10 operation, and even a lack of political acumen at the top. Yet there are still enough veterans of Blair’s early days to reassure Starmer that his predecessor’s first months have been viewed through rose-tinted spectacles, glossing over a damaging rebellion over benefit cuts for single-parent families, and the Bernie Ecclestone Formula One lobbying scandal.

Starmer came into office aware that public opinion was not on his side, acknowledging in his Tate Modern rally late on election night that showing politics could be a force for good was the “great test” of our era. Just days before, a YouGov poll found that even among those who planned to vote Labour, more than 40% did not have high hopes.

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But while his first three months have brought successes at home and abroad, his government has been beset by rows not just over donations and internal power struggles at No 10, but over the tough economic choices ahead, as well as questions over his political judgment that have left many in his party feeling jittery.

Those who work most closely with Starmer say that his strength is “keeping his eye on the horizon” and being unswayed by what he sees as obstacles along the way. “I knew from observing previous governments that you’re going to get side winds all the time,” Starmer says. “But my line of sight is on what I’ve got to have delivered after one five-year term, and a decade of national renewal.”

Yet even those close to him accept he doesn’t always appreciate how aloof that approach might appear. “We all hope it’s teething troubles,” one senior Labour politician confides. “But we all worry in case it’s something worse.”

Finally, after warnings from senior aides and cabinet ministers to “get a grip”, Starmer came to the conclusion that some of those side winds risked blowing the government fully off course. His response: Gray would have to go.

One of Starmer’s first tasks on entering office was to pick his cabinet. He had always planned to transfer his shadow team straight over into government roles, with a few tweaks. The reshuffle appeared to go smoothly. But behind the scenes it was more fraught.

“We had to work out who had held their seats and where everybody was. Hilary Benn was still in Leeds. Steve Reed was late because he was at home in his shorts,” one aide says. They were given the Northern Ireland and environment briefs. “After Shabana [Mahmood] was offered justice secretary she panicked about whether she was also lord chancellor, which usually goes with the job, and tried to get back into the room to check.” She was reassured that was the case by civil servants. “Liz [Kendall] was so emotional she was in tears.”

The arrivals didn’t go entirely to plan. They had been carefully choreographed so the most senior ministers would get there first. But Yvette Cooper and David Lammy, as home and foreign secretary respectively, had their movements controlled by their security teams, and in the meantime Wes Streeting sauntered up the street.

Initially at least, the rest of it went as hoped. Just four days after taking office, Starmer flew to Washington DC for the Nato summit. “It’s a gift from Rishi,” he chuckled to officials. It was a useful early opportunity to meet world leaders while the electoral gold dust was still glimmering, and they all were keen for some to rub off.

Starmer paid his first visit to the White House at the height of speculation over Joe Biden’s future. The two men discussed the “special relationship” and wider global affairs. But officials who had followed the UK election campaign closely were amused when they touched on their fathers, and Starmer volunteered that his was a toolmaker.

Later, on his third visit to the US as prime minister, he would meet Donald Trump for a private two-hour dinner at Trump Tower in New York, riding up to his penthouse in the garish gold elevator amid heavy security after two assassination attempts. Labour was on a charm offensive after senior party figures criticised the former president in the past, with Lammy, who attended the dinner, previously describing Trump as a “tyrant in a toupee”.

“He came up from Florida for it, so he took it really seriously,” Starmer says. “He’s different in private than he is in public. The way he engages in conversations, the way he addresses issues. He’s more thoughtful.” Trump was curious about how Labour had won back the “red wall” to secure such a huge election victory, sources say, perhaps with an eye on how the rust belt states in the US could play a similar role in his own re-election campaign.

Back home, Labour’s first king’s speech initially went off without a hitch, bringing in bills to nationalise the railways and establish Great British Energy, improve workers’ rights and change planning rules to build more houses. In a frenzy of activity, ministers scrapped the Tories’ Rwanda scheme and set up a border security command to tackle small-boat crossings. They invited Ukrainian president Volodymyr Zelenskyy to Downing Street, and took first steps to reset relations with the EU. They reached pay deals with junior doctors and train drivers, and funded above-inflation public sector wage rises, helping to reverse years of decline.

But just two weeks into office, Starmer faced his first major test, a Commons rebellion calling for the two-child benefit cap to be scrapped. Inside No 10, it was seen as an early and not entirely unhelpful opportunity to flex their muscles with Labour backbenchers, particularly on the left. Outside, though, it filled many MPs, including some in the cabinet, with dismay. “If we’re not tackling child poverty, what are we?” one said at the time.

All seven rebels, including veteran leftwinger John McDonnell, were stripped of the whip for six months. The government announced a child poverty taskforce, but it did little to stem despair across the party, and the wider public, over such a symbolic issue.

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Starmer had always been clear there would be tough choices ahead given the state of the economy, and wanted to pin the blame on the Tories as fast as possible. Over in the Treasury the chief secretary, Darren Jones, joked that he had gone through his desk drawers in case his predecessor had left him a “no money left” note.

Within days of becoming chancellor, Reeves announced the Treasury would be carrying out an audit of the fiscal inheritance – one of the worst since the second world war. It found a £22bn black hole in government spending plans for essential public services in 2024-25. Labour immediately leapt on the deficit as evidence of irresponsible management of the economy, paving the way for tax increases and painful spending cuts in the budget. But to help fill the black hole, they made what many regard as their biggest mistake: cutting the winter fuel payment.

Reeves has been bullish – in private and in public – about the decision, arguing that she had no choice and that the axe would otherwise have fallen on support for disabled people or families with children. “There’s no way I’m doing that,” she is said to have told angry MPs.

She has doubled down on her “iron chancellor” image, which aides believe has helped restore the party’s reputation for fiscal competence. In one political cabinet meeting, Ed Miliband, highlighting radical decisions made in straitened times, paid tribute to Labour for setting up the NHS in 1948 when rationing was still in place. Later, a minister was overheard teasing him for giving Reeves ideas. “Rationing?” she quipped. “I’ll make a note of that.”

Many cabinet ministers are uncomfortable about the choice – and worry it will be weaponised by the Tories this winter – but for now are staying quiet. “[Reeves’ team] listened to the Treasury civil servants, rather than thinking about the political impact,” complains one senior party figure. “They’ve handled it appallingly,” adds a cabinet minister.

Starmer admits it was one of the toughest choices he has had to make in government. “Of course it is. Of course I understand and respect people’s concerns,” he says. “But I deeply and strongly believe that we’ve got to stabilise the economy.”

But one No 10 Labour adviser speaks to a wider anxiety. “People think it gives them an insight into how Labour will govern. They worry that what we’re going to do is hit people like them. They’re waiting for the moment of betrayal after so many years of being let down.”

Internal frustrations within Starmer’s top team, which had been kept at bay by the election, began to bubble over, with Gray increasingly becoming the lightning rod. Some political colleagues accused her of “control freakery” and creating a “bottleneck” in No 10 that had delayed policy decisions and appointments.

“Before the election she said that cutting the number of spads was about ensuring the civil service ran things,” one campaign insider claims.

Special advisers, even usually loyal ones, were especially forthcoming in their criticism, with conversations quickly turning to how she handled their contracts and salaries. Their anger exploded into the semi-open when it was leaked that Gray was paid more than the prime minister.

“There’s a bunch of political advisers who could get access to Keir whenever they wanted in opposition,” one source said at the time. “But now they can’t – that’s not how government works – and they don’t like it. Sue is protecting his time. She’s just doing her job.”

Preparations for government had been put in the hands of Gray and a small team of party officials, working at a secretive office around the corner from Labour’s HQ in Southwark. Visitors were discouraged. “We were told Sue had a plan, and to keep our noses out of it,” says one campaign adviser. “But she clearly didn’t.”

One view is that some of Downing Street’s early problems could have been avoided if they had spun a clearer narrative around all the activity. “There was no big set of announcements to capture that spirit of change,” says an insider.

Gray was getting the blame for many of the missteps. It had become unsustainable. At the end of last week, Starmer summoned her to a meeting, at which he told her that she would have to go. McSweeney was appointed chief-of-staff in her place, supported by two deputies and a new director of strategic communications; there are hopes of calmer waters. “I want to make Downing Street boring again,” McSweeney is said to have told officials.

If the reset at the top fails to deliver, there is nowhere left to hide.

But Starmer believes they’re now on track. “You will always get people giving a view, of course. I do it myself in Arsenal games, as do 59,999 other fans. It’s the same in politics. But only the manager knows the gameplan for this match.”

At the end of July, Starmer’s plan to make a speech warning that “things will get worse” before they get better was blown off course by a horrific stabbing at a dance class in Southport, which left three young girls dead, sparking a series of far-right riots that spread nationwide. His response was unequivocal. As rioters threw bricks at police officers, set vehicles on fire and attacked a mosque, the prime minister warned they would “feel the full force of the law” and be hauled in front of the courts within one week. He was fearful the situation could spin even more out of control. “When people tried to set fire to a hotel in Rotherham, that was the point where I was really worried,” he says.

In the first emergency Cobra meeting on the riots, he was presented with official data that showed there were just five spaces available in jails in the north-west of England. “Keir’s eyes almost popped out,” one attendee says. Yet the crisis played to Starmer’s strengths, including his experience running the Crown Prosecution Service during the London riots in 2011, and after a week the disorder subsided, leaving the country scarred but his own reputation enhanced.

By then, however, the Commons was in recess and everybody was on holiday, so his plan for a speech was delayed. When the moment finally came, most people were enjoying the late-August sun and the news that Oasis were reuniting. It seemed an odd time to bring them back down to earth with a bump. “I have to be honest with you: things are worse than we ever imagined,” Starmer said, setting off a ripple of anxiety among Labour MPs, many desperate for the government to offer some hope after their landslide victory.

Downing Street brushed aside the jitters. “They need to get over it,” said one source at the time. “The public is sick of boosterism. Boris Johnson overpromising and underdelivering is a big factor in why people have lost faith in politics.” But within weeks, consumer confidence had fallen sharply amid growing fears over how much pain the budget would inflict. Many ministers felt the bleak outlook had been a mistake and could damage the push for growth. “The miserablism was totally self-defeating,” one Labour figure says.

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No 10 strategists have since admitted they overdid the negativity, sending out Pat McFadden – described by one colleague as a man who “could make an undertaker look cheerful” – to roll the pitch. “We may need to adjust the treble and the bass a bit, but the tune is the right one,” a source insists.

In late August, it emerged that Lord Alli, a long-term Labour donor who ran fundraising during the campaign, had been given a Downing Street pass, signed off by Gray. Nobody seemed clear why. “Waheed is a millionaire and he already has a peerage,” said one cabinet minister. “What more can he possibly want?”

The damaging headlines continued. Alli was also Starmer’s biggest personal donor, giving him tens of thousands of pounds for designer glasses, clothes – including for his wife – and the use of a penthouse apartment during the campaign, which he later justified by saying his son needed somewhere quiet to study for his GCSEs. The hashtag #FreeGearKeir began trending on social media.

Alli, who has an estimated £200m fortune, also loaned Rayner his luxury Manhattan apartment over New Year and paid for education secretary Bridget Phillipson’s 40th birthday party, as well as clothes for the deputy prime minister and Reeves. Cabinet ministers watched in incredulity as the stories kept coming.

McFadden was overheard accusing the media of false equivalence. “There’s an attempt to say we’re all the same. I don’t believe that,” he said. Starmer agrees. “Look at what went before – Covid contracts, not actually complying with the rules, lying to parliament. It is a million miles away from all of that.” But the defiance risked blinding Labour to the obvious point: that the public has little patience for Westminster scandals. Telling them no rules have been broken or the Tories did worse does little to change that.

The government eventually moved to shut down the row, saying that top ministers would no longer accept free clothes, and changing the rules on declaring interests and hospitality, while Starmer repaid some of the gifts – including Taylor Swift tickets – he had received since becoming prime minister, although not his free Arsenal tickets.

Inside Labour, though, there is exasperation at how No 10 has handled the row. Some feel Starmer’s argument that he was saving the public purse in security costs by watching the football in a corporate box was flimsy. One aide tries to explain: “Keir regards it as tittle-tattle, a distraction, so his instinct is to ignore it.” Starmer himself tells me: “The moment I allow myself to get too bogged down in the side winds is the point that other governments have gone wrong in my view, because they’ve lost sight of what the real point of government is.”

However, he later admits that he does understand the public aversion to politicians receiving gifts. “Yes, I can see that. I can see why you and others ask as many questions as you can.”

The political and media environment that Starmer has walked into is entirely different from what has gone before. “There’s a naivety about what a knife-fight politics is today,” a senior official says. “Nothing is off limits. It’s a very brutal learning curve.”

Starmer’s friends say he has found the last few weeks, when his own family has been dragged into the donations row, particularly difficult. He is acutely aware that his teenage children, a son and a daughter, are at an impressionable age.

“These things are never easy, but I suppose they’re part of the territory,” he tells me. “I’ve had versions of this before. I had it with Durham and beergate. I’m not going to pretend it’s pleasant, but it wasn’t a first-time experience, and I doubt it will be a last one, either.”

Before he took office, Starmer promised his family he would try to keep Friday evenings with them sacred. “It has been a bit of a struggle, to be honest, because there’s been so much going on, but we’re still trying to carve out time,” he says. The family has installed Sky TV in the flat, so they can watch the football together.

He wakes at 6am and spends the next two hours reading, before meetings with his top team. He usually heads upstairs to see the family around 8pm, and will do a bit more reading after the News at Ten, before heading to bed. He admits it feels “a bit odd” living in the Downing Street flat (where aides say the wallpaper installed by Boris Johnson is more muddy yellow than gold), but at least “it’s the shortest commute I’ve ever had”. It also means, for the first time in years, he sees his children when they get home from school. “Even if I’m in a meeting, and all I can do is say hello, give them a kiss and send them upstairs.”

When the riots kicked off, Starmer cancelled his family holiday to Italy. Friends say he was exhausted after the long buildup to the election, but felt he should stay, especially when police were being asked to cancel leave. “Don’t get me wrong, I don’t think that cancelling your holiday is a good thing,” he tells me. “I don’t believe in this sort of politics that says, you know, anybody that has a day off is a poor decision maker.”

Yet for all the difficulties navigating family life in No 10, officials and aides alike say that Starmer is more temperamentally suited to the role of prime minister than leader of the opposition. “There were times when he was utterly miserable,” one friend says. “He would sit with his head in his hands in frustration at not being able to do anything.”

Starmer increasingly spends his days in Downing Street working in the study upstairs, rather than the office used by most of his predecessors, having replaced the portrait of Margaret Thatcher that used to hang there with a landscape painting after feeling unsettled by her constant gaze. He has lunch at his desk, and is back on Pret tuna baguettes, having sworn off them in the campaign after eating them every day for five weeks, and drinks strong cups of tea throughout the day.

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The civil service has had to get used to “Keir time”, with Starmer openly disapproving of anybody who turns up even a minute late to meetings. But officials say he is the first prime minister since David Cameron to trust his cabinet to get on with the job.

Some ministers remain worried about living up to the weight of public expectation. They want him to better articulate what that change might look like, rather than just getting on with the job. In his conference speech, Starmer turned the dial, telling his audience he understood their impatience for change. He tells me there was a need for “a bit of sunny uplands”, and recognises that people are scared of being disappointed.

“I have a heavy responsibility. My job is to deliver and I’m going to get judged on delivery. In the end, I want people to be better off under a Labour government. I want to be able to look people in the eye and say we’ve changed the way our economy works, so you are better off.”

The budget later this month is unlikely to make him any more popular, with his personal ratings plunging to -30 after the conference. No 10 is undeterred. “You can’t say you’re going to do unpopular things and then say, ‘Oh my God, they’ve made me unpopular,’” a source says.

Most Labour insiders believe the government can bounce back now that the new No 10 operation is in place. “It’s not like Liz Truss fucking the economy,” a source says. “None of this is terminal.”

By the time of the next election, they believe, the country will be back on its feet, and voters who put their faith in Labour last time round reassured. Another insider is more succinct: “It’s all about delivery now. And if we don’t deliver, we’re fucked.”