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It’s just after 9:30 p.m., and Boris Johnson’s chief of staff, Edward Lister, is finally sitting down for dinner with a colleague in the corner of Mr. Cooper’s Restaurant and Bar in Manchester’s Midland Hotel. The next day is make or break time: Johnson will unveil his new Brexit plan, which the prime minister hopes will fire the starting gun on a frenetic two-week sprint to reach an agreement with the European Union on the terms of Britain’s withdrawal. If he fails, he is almost certain to miss his own “do or die” deadline to take Britain out of the bloc by October 31. Lister, 70, is an unassuming figure, besuited, gray-haired, respectable, like the head of a medium-size business. One of Johnson’s most trusted advisers from his time as London mayor, Lister is a stark contrast to the other central figure in Johnson’s administration, Dominic Cummings, an anarchic force of nature consumed by Brexit. Ultimately, Lister’s role in the Brexit negotiations is more atmospheric than pivotal: Cummings is the driving force inside 10 Downing Street, whereas the intellectual energy on Brexit is created by David Frost and Oliver Lewis, the two officials tasked with working up detailed plans for a possible agreement and the prospect of “no deal,” respectively.

Yet nothing could happen without a diplomatic breakthrough forced by Johnson—and Lister’s role, as the Conservative leader’s personal emissary, is to help protect a key back channel with Ireland that the prime minister has opened up. This tenuous line of communication between London and Dublin is helping to keep the flickering chances of a Brexit deal alive amid the gale-force political winds of Westminster. Lister had been dispatched to Dublin earlier that day, October 1, on a courtesy mission. The following day, Johnson would deliver a set-piece speech to Conservative Party activists and publish his long-awaited Brexit plan soon after. Lister visited Dublin with one goal: Keep the window open for a deal. It was crucial the Irish not kill Johnson’s hopes with their reaction. This encounter and other one-to-one meetings between the British prime minister and his Irish counterpart Leo Varadkar, which would reshape Brexit and Johnson’s premiership—accounts of which I compiled based on conversations with five senior officials in London, Dublin, and Brussels who had knowledge of the talks, all of whom requested anonymity because of the sensitivity of the meetings—reveal a fundamental tenet of his approach to leadership: It is one rooted in personal rapport, face-to-face diplomacy, risk taking, and instinct, in which everything orbits around him and his personality. Different officials with different briefs, skill sets, and attributes work around the prime minister and are expected to be ready when an opportunity arises, deal or no deal, domestic politics or foreign policy. It is down to Johnson to create these opportunities.

They also reveal a wider lesson of politics: personality matters. Britain’s Brexit negotiations have largely been characterized as ones that are legal and technical in nature, to be decided by nation-states and international organizations—whether British financial firms will be able to offer their services in the EU after Britain leaves, whether EU nationals can stay in Britain, or how sales tax should be administered when the two sides split. And, to be sure, those are key issues to resolve. Yet often lost are the roles of politics and the individual—the human element, in which such intangible concepts as momentum, confidence, trust, or popularity work to create openings or close them down. Lister’s mission to Dublin was not the pivotal moment in the process—that would come later—but it reveals how much Johnson’s way of working sharply differs from that of his predecessor, Theresa May. It is an approach which ultimately allowed him to pivot quickly, creating the space to seal a deal with Varadkar and later the EU, and leaving his officials to fill in the details. When he delivered the news of Johnson’s proposal, Lister’s counterparts in Ireland were furious, according to an official with knowledge of the meeting. Johnson was about to propose two things almost certain to be rejected by the Irish government: First, a customs border between the Republic of Ireland (an EU member state) and Northern Ireland (a part of the United Kingdom); and second, a mechanism for Northern Ireland’s unionist, pro-British community to give their consent to any new arrangements that would be in place after Brexit.

But when the British leader went public with his plans the next day, while the Irish voiced their displeasure, they did not torpedo the prospects of further discussions. At that stage, that was enough. The meeting in Dublin was a difficult one, but what prevailed was a spirit of cautious trust between the two sides, one that had been built on a budding relationship between the two men who have come to define the prospects of Britain and the EU agreeing to an orderly withdrawal deal: Johnson and Varadkar. Theirs is a relationship that has had only weeks to grow but that has hinged on a few key moments, beginning with a tense introductory discussion in early September; followed by a meeting on the sidelines of the United Nations General Assembly in New York City, in which Varadkar bonded with a despondent Johnson; and culminating in one-on-one talks in rural England which paved the way for the deal which was later agreed to in Brussels. Johnson must still get this Brexit deal through Parliament—and has now accepted he will only be able to do so if he wins a general election first—but the past six weeks have nevertheless illustrated the strengths of his approach. He has reopened a deal May reached with the EU, something the bloc had said it would not countenance; completely reimagined the contentious Irish backstop, which has been a crucial hurdle to any agreement (and remains so); and radicalized Brexit toward a much “harder” divorce, while also managing to build a majority in Westminster that, for the first time, voted for a negotiated exit in principle. It was this final political victory which changed the game in London, forcing parliamentary opponents of Brexit to change tack, giving up hopes of an immediate second referendum on Brexit in favor of a general election, set for December.

Yet, while the events of the past six weeks have revealed the strengths of Johnson’s brand of instinctive, personality-based leadership, they have also exposed its limits: Since the deal was struck with Varadkar, the reality of Johnson’s compromise has begun to emerge, calling into question how much he was on top of important details. This six-week period, whose ultimate success or failure has yet to be established as Britain gears up for the most defining election in at least a generation, nevertheless stands as a test case to the possibilities offered by raw politics, personal chemistry, and diplomatic effort—as well as their limits. However far Varadkar and Johnson were able to move the dial, neither could solve the toxic reality at the heart of Brexit: An economic border must go somewhere, and wherever it lies, someone is going to pay a high political price. An almost universal view among senior officials on both sides of the Irish Sea is that the pivotal moment in Johnson’s Brexit renegotiation was the hastily arranged summit in northwest England on October 10, just over a week after Johnson’s Conservative Party–conference speech. It saw both sides make significant concessions, creating a so-called landing zone for a final agreement that was then hurriedly put together by U.K. and EU officials in Brussels. According to those involved in the diplomatic effort who are close to Johnson and Varadkar, however, none of it would have been possible without the initial opening created in Dublin just a month earlier, on September 9, when the two leaders met for the first time.

It is a counterintuitive conclusion: The initial reaction had not been great. The pair spent only 40 minutes together and agreed on nothing tangible, according to three officials with knowledge of the meeting. The Irish leader had been blunt in his message to Johnson at a joint press conference before their talks, warning that there was no such thing as a clean Brexit and that Britain could not escape its obligations to Northern Ireland by simply walking away from the EU without a withdrawal agreement (Johnson had spent the preceding weeks threatening just such a no-deal Brexit).

Still, on the way back to London that day, on board a small Royal Air Force plane with his closest advisers, Johnson had been in a buoyant mood, full of bravado. “We’re going to get a deal,” he declared to his aides, pacing up and down the aisle, throwing his arms out wide and pushing out out his chest, according to one firsthand account. At this point Johnson had been prime minister barely a few weeks, but the mood had changed inside 10 Downing Street. A new team had moved in, with new tactics and ideas. It had already suspended Parliament—a move that had yet to be declared unconstitutional by the Supreme Court—and its poll numbers were looking good. While nothing of substance had been achieved in Dublin—indeed, even now, with the House of Commons yet to ratify a Brexit deal and the EU once again delaying Britain’s departure from the bloc, Johnson could still be said not to have achieved anything of substance—the British leader had still come away from his meeting with something unquantifiable: an opening. According to officials, Johnson had simply wanted to convince Varadkar that he wanted a deal, and that message landed. In Dublin, I was told, the Irish leader and his team got the clear impression that despite Johnson’s gung-ho promises and “do or die” commitments to leave the EU on October 31, he was actually someone whom they could work with. “They were personality meetings,” one official involved said. Johnson “did a bit of freewheeling, but he convinced Varadkar he wanted to do a deal.” A second official confirmed that account, saying Varadkar “came away thinking we can do business.”

The contrast between Johnson’s relationship with Varadkar, even in those early days, against that of his predecessor’s with the Irish leader could not have been clearer. May’s instincts were toward caution, detail, and hard work over more ethereal concepts like trust or warmth. She spent months weighing the risks and rewards of different options before making a decision, failing to build momentum and letting potential openings slip by. Throughout her three years in power, despite being seen in Dublin as grown-up and serious, she did not develop a personal relationship with Varadkar or senior EU figures like Donald Tusk, the president of the European Council. Even behind closed doors, May stuck so rigidly to script that Irish officials saw it as almost offensive, aides told me. At a meeting before the publication of some key British proposals, according to one account given to me, Varadkar asked what he should expect. May smiled and said he would have to wait until it was published. Johnson’s meetings with Varadkar point to a different modus operandi entirely. In many ways, he is an atypical politician—anarchic, short on detail and long on jokes. Yet in others, Johnson is actually more über-politician: high on showmanship and charm, with vaulting ambition and self-confidence; prone to ups and downs and angst, and curiously susceptible to criticism. After the first meeting in Dublin, having concluded, cautiously, that Johnson was willing to compromise to get a deal, Ireland took a risk: It began talking to the British on the substance of Brexit. Officials in 10 Downing Street also believe that Johnson’s commitment to preparing for a no-deal exit, and apparent willingness to go down this route if he could not reach an agreement, played an important role in encouraging the Irish—and the EU—to the negotiating table. For years the Irish government, particularly after Varadkar became prime minister in June 2017, had insisted negotiations be channeled through Brussels. Some bilateral communications took place, largely thanks to a close relationship between May’s deputy and his Irish counterpart, but the real negotiations were strictly an EU matter as far as Dublin was concerned. In September, the Irish began, bit by bit, to dilute the purity of their position.

Following the September talks, a back channel was set up between 10 Downing Street and Varadkar’s office in Dublin. The Democratic Unionist Party in Belfast was kept in the loop. The DUP was Johnson’s parliamentary ally in Westminster, but a major roadblock to a Brexit deal. The arrangement was not without risk: If Dublin was drawn too far from the position Brussels had held for three years, the EU—which has successfully insisted its member states act as one in Brexit negotiations—might reasonably respond with fury. In the end, it was seen as a risk worth taking. Throughout, there were concerns in the minds of Irish officials that they were being played—that any movement in private would be used against them in public by Johnson’s more hard-line Brexit-supporting staffers. This fear never went away, but was slowly overtaken by the sense that Johnson was for real. At the core of this calculation was the emerging relationship between the two leaders, which was further cemented when they met in New York City later in September. It was at this meeting, on September 24, that Varadkar glimpsed a different side to his British counterpart, widely seen as the caricature that Johnson himself created: bumbling, chaotic, and amusing, but ultimately not serious. At the UN, Johnson was tired and distracted by events at home, where the Supreme Court had ruled his suspension of Parliament unconstitutional, and was unable to hide his vulnerability.

According to three people familiar with the events, Johnson’s demeanor that day had the effect of drawing Varadkar out. Both leaders went off-script, going back to the basics of Brexit and offering ideas, Johnson gesticulating with his arms in a physical expression of frustration that they had not found a compromise. The meeting—a moment in which one national leader who understood the vicissitudes of political life saw the struggles of a counterpart—revealed a genuine desire on both sides to find a compromise. Varadkar, according to one senior official, concluded that despite Johnson’s political difficulties at home, a deal was still possible. “The currency between leaders,” the official said, “is something they both understand.” By the time Johnson and Varadkar met on October 10 in northwest England, a turning point appeared to have been reached. Two days prior, the British leader had been on a testy phone call with German Chancellor Angela Merkel, details of which Johnson’s aides leaked to the press. The conversation bode poorly, but the fact that only British officials were briefing the contents of the exchange worried the Irish: Would they soon also find themselves on the sharp end of a hostile anonymous briefing from Johnson’s aides, potentially fracturing European unity on the Brexit issue? After the Merkel call, Johnson got on the phone with Varadkar and said they needed to meet. Varadkar agreed, a sign that a baseline of trust had been established. The two leaders, by that point, had built enough of a relationship that the risks—of a backlash domestically, or from Brussels—were still worthwhile.

It was Varadkar who suggested the site of the meeting, an apparently neutral venue near Liverpool, an English city with a substantial Irish population. Irish journalists were only informed at 5:50 the previous evening, receiving an email telling them that the two leaders would hold talks at an undisclosed location and that no media would be allowed to attend. (Infuriated, four Irish reporters went to Liverpool anyway, frantically going from one potential site to the next, making educated guesses at which venues might be suitable, eventually stumbling upon Thornton Manor. There, they were greeted by serious-looking men with distinctive pin-badges—protection officers from the British police’s Special Branch. Shortly after, they saw Varadkar and his officials being driven into the estate.)

Inside Thornton Manor, a grand provincial hotel and wedding venue, large entourages of British and Irish officials gathered, and waited. Among them were the British ambassador to Ireland alongside his counterpart, the Irish ambassador to Britain, as well as aides from both sides and the head of each country’s civil service. They had long been preparing for such an eventual head-to-head, game-planning what the other might offer, and how far they could go themselves.

Yet once at the site, they were all kept apart from Johnson and Varadkar, who sat, one-on-one, in a separate room for an hour and a half. Until this meeting, indeed only two days before, Johnson was clear there could be no customs checks within the U.K. (between Northern Ireland and Great Britain) and insisted that once the U.K. left the EU’s customs bloc, they should be placed on the island of Ireland somewhere away from the border. The EU, however, had insisted that if the U.K. was intent on leaving the European-wide customs zone, checks would have to take place between Britain and Northern Ireland, viewing this as a compromise between guaranteeing some measure of security on the island of Ireland, where a largely invisible border was seen as a foundation of peace following decades of violence, and ensuring the inviolability of its bloc-wide market. Equally, the Irish government had been clear that Northern Ireland should not be given special powers to “consent” to any deal, because the region had voted against leaving the EU and in any case had not been given such powers over international treaties in the Good Friday Agreement, which ended the 30 years of bloodshed there. In the meeting, though, both leaders changed their positions to a remarkable degree, going further than either side’s officials were expecting, according to those I spoke with. Johnson gave way on customs and Varadkar agreed to allow Northern Ireland a voice to consent to any deal imposed upon it. In effect, a simple majority of Northern Ireland’s elected lawmakers could erect a border on the island of Ireland—the exact scenario Ireland and the EU have sought to avoid.