The first time Keir Starmer met Donald Trump, the prime minister had a convivial two-hour dinner with the then presidential candidate in his luxury New York apartment, before Trump dimmed the lights to show off the Manhattan skyline.
The stakes at the two leaders’ second meeting at the White House this Thursday will be much higher. It will take place days after the third anniversary of Russia’s full scale invasion of Ukraine, amid tensions at the United Nations and during a turbulent period in transatlantic relations.
Starmer is hoping to ease tensions, officials say, including by avoiding directly referring to the president’s attack on Volodymyr Zelenskyy as a “dictator” or his accusation that the prime minister and Emmanuel Macron, also in Washington this week, had done nothing to stop the war.
Downing Street has, to date, adopted a cautious response to the slew of contentious announcements and comments that have come out of the White House since Trump began his second term. The strategy this week will be no different.
“We don’t want to rile Trump, that would be totally counterproductive both to our interests and those of Ukrainian and European security,” one aide said. “We’re much more interested in what he actually does, rather than what he says. So far, we think there’s a difference.”
But No 10 knows the meeting will be the biggest test yet of Starmer’s diplomatic and negotiating skills, as he tries to balance the UK’s security and economic interests with retaining good relations with the unpredictable president. It could also be a gamechanger at home.
Starmer has always said that personal relationships are his starting point for diplomacy, and his team knows that he will have to play the man, as well as the ball. “Will Trump still be saying Keir is a ‘nice guy’ at the end of it? We don’t know that, but we hope he will respect him,” an aide said.
Key to that, officials believe, will be making sure that at the end of the meeting, Trump feels like he is emerging triumphant. “Whether it is on Ukraine or on trade or on China, we will need to convince him that America is getting something out of it,” one added.
At the Scottish Labour party conference on Sunday, the prime minister said that “peace only comes through strength” – an echo of the central idea of Trump’s “America first” foreign policy. But in an article last week he had gone on to warn: “The reverse is also true. Weakness leads to war.”
Downing Street has made clear that Starmer will carry tough messages into his meetings with Trump, insisting that Ukraine must be “at the heart of any negotiations” with Russia, otherwise any peace deal would fall apart, and that the US should be wary of trusting Putin.
He will argue that this is in the US’s interest – with Ukraine’s future a decisive issue not just for itself, but for wider European security – as leaving the continent insecure could both strengthen China and damage the US economically.
Perhaps aware that Trump’s vanity is one of his more reliable traits, Starmer may make the case that a fair outcome would also benefit Trump’s own legacy. History would judge any deal which emboldens Putin to be a bad one. Macron is likely to make the same point.
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In Scotland, Starmer told his party that the US was right to say that Nato allies must do more to ensure their own defence, rather than relying on their largest partner. “It’s time to take responsibility for our security,” he said.
He is expected to tell Trump the UK will raise defence spending to 2.5% of GDP by 2030, in line with Labour’s election manifesto. But advisers admit the prime minister may have to show a willingness to go further, although they downplayed expectations of an announcement this week.
Starmer will set out how the UK can offer practical support on defence – including putting boots on the ground in Ukraine for a peacekeeping force. He has already indicated this would be contingent on a US “backstop” of air, logistics and communications support.
Putin, more than anything right now, appears to want sanctions relief, and the UK will be urging Trump to resist. David Lammy, the foreign secretary, who is expected to accompany Starmer to the White House, is this week announcing the largest sanctions package against Moscow since the early weeks of the war.
While Ukraine will inevitably dominate the talks, Starmer will also try to persuade Trump to avoid targeting the UK with tariffs, reminding him the UK runs a trade surplus with the US. The Chagos Islands deal and plans to reconstruct Gaza are also on the table.
The UK knows the usual rules of diplomacy – including that such conversations remain private – will not apply. Straight after their talks, Starmer and Trump are expected to hold a news conference. Whether the meeting has been a success – or otherwise – is likely to be clear immediately.