Inside the Dysfunctional Relationship of Donald Trump and Theresa May

Forget closer transatlantic ties and a state visit to London, it’s been a year of public clashes.
Illustration: Lorenzo Gritti

When Theresa May returned to the grandeur of the British Embassy on Washington’s Massachusetts Avenue in January last year, her aides had no idea how spectacularly awry her visit to Donald Trump’s White House had gone.

Debriefing her advisers, the U.K. prime minister remembered something: “Oh, yes,” she said. “He did hold my hand at one point.” Already fearful of the political fallout at home from getting too close to Trump, the astonished officials asked if the incident had been captured on camera. “Yes, I think so,” May replied, according to people present.

Theresa May and Donald Trump at the White House.
Photographer: Christopher Furlong via Getty Images

The resulting image, splashed on British front pages, came to define her visit, the first by a foreign leader after Trump’s inauguration. What May’s entourage couldn’t have predicted is that the gaffe would also turn out to be the high point in the first year of the latest incarnation of the “special relationship” between the U.S. and the U.K.

Just under 12 months later, the two are due to meet in Davos at the World Economic Forum on Thursday, and there’s unlikely to be any hand-holding. In that time, the alliance first coined by Winston Churchill and famously nurtured by Ronald Reagan and Margaret Thatcher in the 1980s has become increasingly dysfunctional and at its least cordial in decades.

The transatlantic ties are critical to May’s administration, while just convenient for Trump. The U.K. needs to forge new trade partnerships after leaving the European Union. The U.S. wants to reconfigure some of its relationships to protect American companies.

Rather than a tighter bond, a promised state visit and a future trade deal, Trump and May have clashed repeatedly in public—over intelligence leaks after a terrorist attack in Manchester, the Iran nuclear deal, and most dramatically after the president tweeted a message from a British far-right anti-Muslim campaigner.

“As the U.K. negotiates its departure from the EU it wants to be able to emphasize its Atlantic relationship,” said Heather Conley, director of the Europe Program at the Center for Strategic and International Studies in Washington. “The problem is the Trump administration is not providing the U.K. with that balance.”

Many of the current and former officials interviewed for this article asked for anonymity to speak candidly about the uneasy political aspect of the alliance, which is a sensitive matter on both sides of the Atlantic.

When Trump upended the world order by winning the presidency in November 2016, few leaders felt the vibrations as much as May. The soon-to-be U.S. president had supported Brexit and suggested making his supporter and her political rival, anti-EU campaigner Nigel Farage, the new British ambassador to Washington.

Illustration: Lorenzo Gritti

Her officials dismissed it. Matters worsened when it emerged that Nick Timothy and Fiona Hill, May’s co-chiefs of staff, had publicly ridiculed Trump as “a chump” on Twitter before they entered government and urged their colleagues to shun his team. The pair set off on a secret trip to the U.S. to rescue the alliance. Foreign Secretary Boris Johnson followed and soon after May arranged to visit the U.S.

Trump was clearly pleased with the idea. “She’ll be my Maggie,” he reportedly told his aides, referring to Reagan and Thatcher.

In London, Hill was especially keen to keep Trump close. She argued that a strong alliance with America was just what Britain needed in order to make a success of Brexit. The prospect of accelerating a trade agreement with the U.S. was a major goal for the U.K.

Ronald Reagan welcomes Margaret Thatcher at the White House during her official visit to the U.S. in 1983.
Photographer: Jean-Louis Atlan/Sygma via Getty Images

Hill and Timothy planned May’s trip to the White House and took up the idea of offering the president a state visit in return, the highest honor that Britain can give a foreign leader. It would involve the president and first lady staying with Queen Elizabeth II at Buckingham Palace and attending a state banquet in his honor. May's team believed such treatment would appeal to Trump's vanity.

Senior diplomats and the U.K. security services had other ideas, according to some accounts. They wanted May to keep her distance from Trump until he had been office for longer, two people familiar with the matter said. However, one person involved doesn’t recall much internal disagreement.

“It was clear to me and others at the time that an offer of a state visit to President Trump was over the top and unnecessary,” said Katie Perrior, who served as May’s communications director until last June’s U.K. election was called. “Senior diplomats and civil servants both in the U.K. and U.S. raised their concerns through formal and informal routes, warning against rushing into it—and were ignored.”

Ultimately the offer was made. Shortly before May was due to leave the embassy for the White House, an urgent message arrived from from the palace. It said that the Queen had agreed to invite Trump and his wife. May’s officials hastily re-wrote her impending statement moments before her motorcade left for the White House to include the invitation.

Over a meal of blue cheese salad and beef ribs in the White House banqueting room, Trump held forth on a wide range of topics. “The president had strong views on all of them,” recalls Chris Wilkins, then May’s strategy director, who was among the aides around the table. “He said Brexit’s going to be the making of us. It’s going to be a brilliant thing.”

Trump turned to May and told her he believed there were parts of London that were effectively “no-go areas” due to the number of Islamic extremists. May chose to speak up to “correct him,” Wilkins said.

Trump also discussed his British golf courses and his hopes that the relationship with May would be stronger than the Thatcher-Reagan alliance. “It was an hour of the president holding court and the PM being very diplomatic and not many other people saying anything,” Wilkins said.

Illustration: Lorenzo Gritti

It shows the contrast in personalities that make for an unusual relationship, albeit one still underpinned by enduring strategic military cooperation and cultural links. As one British official observed, Trump is a larger than life character and May is almost the complete opposite.

During formal phone calls between the two leaders, May finds it almost impossible to make headway and get her points across, one person familiar with the matter said. Trump totally dominates the discussion, leaving the prime minister with five or ten seconds to speak before he interrupts and launches into another monologue.

In one phone conversation during 2017, Trump complained to May over the criticism he’d been getting in British newspapers. Amid warnings that Trump would face protests in the streets when he arrived, he told the prime minister he would not be coming to the U.K. until she could promise him a warm welcome.

May responded to say such treatment was simply the way the British press operate, and there wasn’t much she could do. In the secure bunker underneath the prime minister’s office, her advisers listened in to the call in astonishment at Trump’s demand.

British officials suspect Trump’s displeasure still lingers. The president canceled a planned trip to London next month for the official opening of the new U.S. embassy building. He claimed he disapproved of a deal to sell the old U.S. diplomatic headquarters. Some in May’s team now regret their “nightmare” decision to offer Trump a state visit.

While the offer of a state visit still stands, British officials don’t expect him to take it up any time soon, or perhaps ever.

“The relationship has taken some knocks,” said Peter Westmacott, a former British ambassador to the U.S. “But there is so much substance to the relationship—commercial, defense, intelligence, foreign policy, cyber, culture, language and shared values—that we all have an interest in ensuring that it remains strong.”

Even if May and Trump patch things up on the slopes of Davos, there’s a cloud on the horizon: another royal invitation.

This time it’s to the wedding of the Queen’s grandson, Prince Harry, and American actor Meghan Markle. None has been forthcoming. But if Trump does make it, at least he might know some of the possible guests: Prince Harry’s famous friends include Barack and Michelle Obama.