5 awkward encounters between UK prime ministers and US presidents 

LONDON — Oh to be a fly on the wall. 

Prime Minister Keir Starmer will meet Donald Trump on Thursday for the first time since the U.S. president returned to the White House. Neither of them will forget the meeting — for the right or wrong reasons.

Although Starmer wasn’t the first European leader to bag time with Trump, the U.K. has prided itself on its so-called special relationship with its ally on the other side of the Atlantic.

But the feeling hasn’t always been entirely mutual. On numerous occasions the duo haven’t seen eye to eye, leading to some, well, awkward encounters.

The PM has engaged in a vigorous charm offensive since Trump’s Nov. 5 victory, speedily congratulating him after meeting him for the first time in September for dinner at Trump Tower. Since then, the unlikely pairing — the buttoned-up British PM and the flamboyant U.S. real estate tycoon-turned-politician — have spoken regularly, with Trump stating Starmer was doing a “very good job.” 

Conversation will be dominated by the war in Ukraine as Starmer tries to convince the president that U.S. security guarantees are essential for any peace deal to work — and that Kyiv and Europe must be part of those negotiations.

But keeping the relationship on track is easier said than done. POLITICO takes you through five occasions that both nations would rather forget and that, temporarily at least, sent the special relationship into a spiral.

Trump and May go downhill 

It would be difficult to find two more different characters than Trump and Theresa May (apart from, say, Trump and Starmer). In any other walk of life, their paths would never have crossed.

They were brought together in January 2017 when May became the first foreign leader to meet the U.S. president after his inauguration. While they talked tough on NATO, the visit was best remembered for the duo linking arms as Trump navigated a White House slope. Despite their close proximity, the relationship never recovered. 

When Trump visited this side of the pond, he slammed May’s strategy on Brexit, leading to revelations he’d told her to sue the EU (yes, really). Upon learning May got paid more than £100,000 to deliver speeches after being PM, Trump fulminated: “I’d pay £100,000 not to hear her talk!” Charming.

Obama and Brown exchange gifts

Exchanging presents with a friend is never a bad idea — unless the gifts differ dramatically in value. Barack Obama and Gordon Brown experienced that very plight in 2009 when the Labour prime minister got the brand-new U.S. president an ornamental pen holder made from the timbers of a Victorian anti-slave ship, a framed commission for HMS Resolute, and a first edition of the seven-volume biography of Winston Churchill by historian Martin Gilbert. 

By contrast, the Obamas got the Browns a box set of 25 American DVDs including “Raging Bull,” “Psycho” and “The Grapes of Wrath” — after which the metaphors for Brown’s political predicament wrote themselves.

Their previous encounter wasn’t much better: After a brief press conference, Brown wasn’t invited to Camp David, and the traditional side-by-side photo op in front of the two nations’ flags was skipped altogether. Later that year Obama turned down no fewer than five requests from Downing Street for a bilateral meeting at the U.N. in New York. Eek.

Bush and Brown go round in circles 

When Tony Blair was in Downing Street he pledged to stand shoulder to shoulder with George W. Bush. Brown, Blair’s successor, didn’t have quite the same flair. His opening line on meeting Bush at Camp David was: “Do you come here quite a bit?” followed by a playful spin on Golf Cart One, where the PM didn’t appear to be living his best life. 

After Brown left office, reports emerged that Bush’s White House had had “grave doubts” about Brown’s suitability to become PM after a difficult meeting with Secretary of State Condoleezza Rice about U.S. policy on aid and development in Africa.

Still, at least at their joint press conference in 2007, Bush called Brown “the humorous Scotsman” rather than “dour” or “awkward.” Take the compliments where you can get them.

Clinton and Major trade fire over controversial visa 

When your BFF leaves office, working with the new kid on the block is always a challenge. Prime Minister John Major’s close allegiance to George H. W. Bush was mothballed after the latter lost the 1992 presidential election to Bill Clinton. Things were never quite the same.

The duo fell out badly when Clinton granted then-Sinn Féin President Gerry Adams a 48-hour visa to speak at a Northern Ireland conference in New York. At the time, Sinn Féin was regarded as the political wing of the Provisional Irish Republican Army, with “the Troubles” over Northern Ireland’s future having killed thousands.

Major also apologized to Clinton personally after the Home Office checked immigration files to see if he’d applied for U.K. citizenship while studying at the University of Oxford to avoid being drafted during the Vietnam War. While the story had no substance, the fact the Home Office did so without Clinton’s knowledge or approval was deeply embarrassing.

No wonder Clinton and Blair looked like a match made in heaven when the latter entered Downing Street in 1997. 

Thatcher and Carter fail to gel 

Margaret Thatcher first came across Jimmy Carter as leader of the opposition in 1977 at Winfield House, the U.S. ambassador’s residence in Regent’s Park, though no record was kept of their conversation.

Their second meeting, later that year in Washington, D.C., went badly wrong. Papers show that Carter took very badly to Thatcher, finding her hectoring and dogmatic, and instructed staff never again to schedule a meeting with an opposition leader.

On the plus side, relations thawed slightly after Thatcher entered No. 10 as the pair supported each other over the Soviet Union’s invasion of Afghanistan and Iran’s taking dozens of American diplomats and citizens hostage at the U.S. Embassy in Tehran — a common enemy clearly helping ties a great deal.

However, their relationship never matched Thatcher’s dealings with Carter’s successor Ronald Reagan. United on the Cold War and economic policy, it was perhaps the best embodiment of the special relationship — and a nearly impossible act to follow.