Moments after Air Force One touched down at Prestwick on Friday for a trip in which politics will take as big a billing as golf, Donald Trump was asked about his relationship with Keir Starmer.
“I like your prime minister. He’s slightly more liberal than I am, as you’ve probably heard. But he’s a good man,” the US president told reporters. At a time when the UK wants Trump’s ear on numerous weighty issues, his response to questions about the “special relationship” will have given Downing Street some reassurance.
But it has been hard won. Starmer has been clear since before Trump’s re-election that he would work with him if it was in Britain’s national interest. There have been uncomfortable moments, but so far his decision to align himself with the US president has broadly paid off.
Most notable was the economic deal agreed by the two leaders that slashes some of Trump’s tariffs on cars, aluminium and steel, and which – even though it is not yet fully implemented – the UK government hopes will be a first step towards a closer trading relationship.
Starmer, along with other western allies, has also helped encourage Trump to shift his position on Ukraine. After initially siding with Vladimir Putin and appearing to blame Volodymyr Zelenskyy for the invasion, the US president has since declared himself “very unhappy” with his Russian counterpart.
The prime minister now faces his toughest diplomatic task of all: trying to persuade Trump to take a different path on the humanitarian crisis in the Middle East. Even getting the issue on the agenda will not have been straightforward, with the White House not regarding Gaza as a priority.
Trump is the only international leader whom the Israeli prime minister, Benjamin Netanyahu, listens to – though even then, not all of the time – so getting the US president’s ear at this precise moment is an opportunity not to be squandered.
With international fury over the situation on the ground in Gaza growing, Starmer has also been under pressure domestically – from his cabinet, Labour MPs and increasingly the public – to take further action against Israel.
Government advisers are defensive – citing what the UK has already done to hold Israel to account since Labour came to power – and promising further action will follow, even if it is not clear what that might constitute.
They point to the UK restoring funding to the UN agency Unrwa, sanctioning far-right Israeli ministers and those who committed settler violence, breaking off trade negotiations with Israel, backing the legitimacy of the international criminal court and restricting arms licences to Israel (though not preventing them entirely).
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The initial urgency is around humanitarian aid, with mass starvation spreading across Gaza, and Starmer will be hoping to persuade Trump that the situation on the ground will only worsen unless the Israelis fully lift their blockade of almost all aid into the territory.
The longer-term prize, however, would be a ceasefire. Starmer will press Trump to revive ceasefire talks between Israel and Hamas, after the US and Israel withdrew their negotiation teams from Qatar last week. Getting them back round the table to agree a 60-day break from fighting is a prerequisite to a more permanent cessation of violence.
The window of opportunity is narrow: the Israeli parliament is not sitting until October, which gives Netanyahu the cover he would need to agree a deal. But Starmer knows Trump is the only international figure who can put pressure on him to do so.
Only at that point does Starmer feel the UK could follow France and formally recognise a Palestine state. No 10 insiders say it is a “matter of when, not if” and David Lammy, the foreign secretary, will be at a UN conference this week to establish a pathway to formal recognition.
To the deep frustration of many in his party, the prime minister last week rejected a call to follow France in recognising Palestine amid concerns the move would be largely symbolic without a ceasefire in place, and that issue could overshadow the talks with Trump.
But that means even more is riding on Monday’s meeting with the US president. It will be a test of whether the energy put into maintaining a good relationship with Trump has been worth it. And it will also show how far Starmer really is prepared to push to help bring an end to the catastrophe in Gaza.
