Prime Minister Keir Starmer’s upcoming meeting with President Donald Trump marks their first encounter since Trump’s return to the White House. While the UK takes pride in its “special relationship” with the United States, that bond has, at times, been strained by political clashes and personal tensions.
Though Starmer was not the first European leader to secure face time with Trump, he wasted no time in engaging with him—congratulating him swiftly on his November victory and meeting him at a Trump Tower dinner in September. Since then, the two have spoken regularly, with Trump even remarking that Starmer was “doing a very good job.”
Yet, keeping US-UK relations steady is never straightforward. As the two leaders sit down, their conversation will likely center on Ukraine, with Starmer attempting to persuade Trump that American security guarantees are critical to any peace agreement. Whether or not the relationship stays on track remains to be seen.
Here’s a look at five awkward encounters that sent diplomatic ties into temporary disarray:
1. Trump and May’s Awkward Downward Spiral
It’s hard to imagine two more contrasting figures than Donald Trump and Theresa May—except perhaps Trump and Starmer. In any other context, their paths would likely never have crossed. But in January 2017, May became the first foreign leader to visit Trump post-inauguration. Their discussions on NATO were overshadowed by the now-infamous moment when they linked arms as Trump navigated a White House slope.
Despite this public show of unity, their relationship quickly soured. During a UK visit, Trump openly criticized May’s Brexit strategy, even revealing he had advised her to “sue the EU.” Later, upon learning that May had earned over £100,000 for speeches post-office, Trump quipped, “I’d pay £100,000 not to hear her talk.”
2. Obama and Brown’s Mismatched Gift Exchange
Diplomatic gift-giving is an art—one that former Prime Minister Gordon Brown and President Barack Obama got terribly wrong. In 2009, Brown gifted Obama an ornamental pen holder crafted from a Victorian anti-slave ship’s timber, a framed commission for HMS Resolute, and a rare first edition biography of Winston Churchill.
Obama’s response? A box set of 25 American DVDs, including Raging Bull and Psycho.
Symbolism aside, the relationship wasn’t much better in practice. Following a brief press conference, Brown wasn’t invited to Camp David, and the customary joint flag-photo op was scrapped. Later that year, Obama rejected five separate requests for a one-on-one meeting at the UN General Assembly.
3. Bush and Brown’s Golf Cart Gaffe
Tony Blair and George W. Bush shared an unshakable alliance, but the transition to Gordon Brown was anything but smooth.
When Brown met Bush at Camp David, his opening line—“Do you come here quite a bit?”—set the tone for an awkward exchange. To make matters worse, he endured a less-than-enthusiastic ride in Golf Cart One, visibly uncomfortable.
Behind the scenes, Bush administration officials harbored deep concerns about Brown’s suitability as PM, particularly after a difficult meeting with Secretary of State Condoleezza Rice on African development aid.
4. Clinton and Major’s Fractured Relations
Few transitions in US-UK relations were as turbulent as the shift from George H.W. Bush to Bill Clinton. John Major, who had enjoyed close ties with Bush, found himself at odds with Clinton from the outset.
Tensions escalated when Clinton granted Sinn Féin leader Gerry Adams a 48-hour visa to attend a New York conference. At the time, Sinn Féin was widely viewed as the political wing of the Provisional IRA. Major was incensed.
Further embarrassment followed when UK officials covertly checked US immigration records to determine whether Clinton had sought UK citizenship during his Oxford years to dodge the Vietnam draft. Clinton was unaware of the probe until after the fact—an undiplomatic blunder that only worsened relations.
5. Thatcher and Carter’s Chilly Reception
Margaret Thatcher’s first encounter with President Jimmy Carter in 1977, while she was opposition leader, went largely unrecorded. Their second meeting later that year, however, was an unqualified disaster.
Carter reportedly found Thatcher “hectoring and dogmatic,” instructing his staff to never again schedule a meeting with an opposition leader.
Relations improved slightly when Thatcher took office, as both leaders aligned on opposition to the Soviet invasion of Afghanistan and the Iran hostage crisis. However, their dynamic never reached the heights of Thatcher’s later alliance with Ronald Reagan—a near-perfect embodiment of the “special relationship.”
Article updated 2 months ago. Content is written and modified by multiple authors.
