A few Republicans have managed—really—to work successfully with the president. Here’s what the new speaker could learn from them.

But there’s no formula for successfully negotiating with this mercurial, ad hoc chief executive. Pelosi’s first attempt to do so, an agreement in September 2017 to protect the Dreamers from deportation in exchange for border security funding, fell apart not long after it was announced.

Still, there’s no reason to think Pelosi, or anyone in the nation’s capital, can’t find a way to a win with Trump. Here’s what we’ve learned about the art of making a deal with Trump from the few successful people in Washington who have figured out how to get what they want out of the president.

Convince Him He’ll Be Loved

Trump may want nothing more than to be well-liked and appreciated. The bipartisan criminal justice reform bill seems to have been sold to him as an opportunity to do just that. Versions of the First Step Act, a major reform that liberalizes federal prison and sentencing laws, had floundered in Congress for years. The policy already had support from across the political spectrum—but it needed a Republican president who could provide political cover to bring enough members of the GOP on board.

Trump wasn’t an obvious champion for sentencing reform. He ran a campaign promising “law and order” and selected the tough-on-crime Jeff Sessions as attorney general. Sessions’ Justice Department had issued reports critical of the bill. The president has suggested that convicted drug dealers deserved the death penalty. To get his support, the criminal-justice reformers would need to conduct a conversion.

The evangelist was White House adviser Jared Kushner, who, all accounts say, worked hard to persuade his father-in-law. Kushner met with everyone from members of the Congressional Black Caucus to Koch-funded interest groups to the news media to bolster an already large coalition. It helped that Kushner was able to deliver plenty of groups and individuals on the right.

“I think the broad popularity of the policy was the gateway,” says one of the bill’s advocates, who watched the process at the White House up close. “The president was also given a booklet of dozens of conservative organizations and individuals making supportive statements on the bill to show grassroots political support. And then it took some convincing that law enforcement was on board.”

The last piece proved crucial, because there’s perhaps no interest group Trump cherishes more than law enforcement. The marquee names—the

• Fraternal Order of Police, the
• International Association of Chiefs of Police, the
• National District Attorneys Association—

were enough to get the president on board. With seemingly few people opposed (Tom Cotton, otherwise a devoted Trump ally, the most prominent) and even staunch critics in the media like Van Jones making the trek to kiss Trump’s ring at the White House, Kushner and his partners succeeded in selling Trump on the most important provision of the First Step Act: Mr. President, you will be loved for signing it.

It won’t be easy for Pelosi, but the Democratic speaker may be able to use similar tactics to goad Trump into supporting some bipartisan health-care initiatives. The administration has already begun proposing some form of federal intervention to lower prescription drug prices, while Democrats have long argued that Medicare should negotiate with Big Pharma on bringing down drug costs. Some kind of compromise bill could get the support of both Capitol Hill and the White House. Your older, Medicare-using base will love you for it, Pelosi might tell the president. That would get his attention.

Remind Him of His Campaign Promises

Earlier this month, Trump and Kentucky Senator Rand Paul were having one of their frequent conversations about the American military presence in both Syria and Afghanistan. Paul, a persistent, longtime critic of the continued deployment of troops in the Middle East, has found the strongest ally of his political career on the issue with Trump.

After their discussion, Paul sent the president some news articles supporting his view that the time was right to withdraw from Syria, says top Paul aide Doug Stafford, who says Trump sent back a note alerting him that he would “see some movement on this soon.” On December 19, Trump announced the forthcoming withdrawal of the roughly 2,000 U.S. troops fighting ISIS in Syria. The move was resisted by just about everyone around Trump, inside and outside the administration, including John Bolton, Jim Mattis and Lindsey Graham. All, except Paul.

“I think people mistake it like Rand is trying to get him to do what Rand wants. But this is what Donald Trump ran on,” says Stafford. “Rand sees his role more as keeping the president where he wants to be and where he said he would be against some people who are inside of the White House and other senators who are trying to push him off of his beliefs and his position.”

Paul’s strategy was partially to ingratiate himself with the man he once, in the primary season, called an “orange-faced windbag.” Trump and Paul have played golf together, a favorite pastime for the president and a way other former antagonists have overcome bad blood.

.. in recent months, Paul has ramped up his public praise for Trump and joined the chorus of Republican criticism for the president’s treatment in the press. Trump has returned the favor with praiseworthy tweets. Paul had raised concerns about two of Trump’s high profile nominations in 2018, for their defenses of the government’s data surveillance apparatus. But he dropped his public skepticism of Brett Kavanaugh and, earlier in the year, did an about-face on his opposition to Mike Pompeo.

Stafford gives credit for Paul’s success to the senator’s constant prodding of the president to be true to himself and his base. “It’s not just Rand’s voice. People who voted for Donald Trump don’t want to still be there either,” Stafford says. “He ran on it, he was loud and clear on it, and he believes it.”

Like opposition to military interventionism in the Middle East, an increase in infrastructure spending is one of the few major Trump campaign pledges that aligns him more with Democrats than his fellow Republicans. Trump’s failure to embrace a major infrastructure bill in favor of the divisive travel ban at the outset of his presidency may have doomed his ability to work across the aisle on the issue. Yet Pelosi could get more than enough of her caucus to embrace some form of new infrastructure spending by reminding the president of his 2016 promise to invest more federal dollars in roads and bridges. If she persists in nudging Trump to fulfill his pledge, Pelosi could deliver a longtime Democratic wish list item.

Stay Outside the Room Where It Happens

Before he was the White House national security adviser being overruled by the president on Syria, John Bolton was arguably more influential with Trump as a private citizen—albeit one with the right platforms to reach him. A fixture on Fox News for the first year of the Trump presidency, Bolton used his cable perch and the host of outlets that would publish him to make an argument directly to Trump: Get out of the Iran nuclear deal.

Trump, who had run hard against what was officially called the Joint Comprehensive Plan of Action, had been persuaded to recertify the deal in early 2017 until the new administration could get off the ground. His national security team, particularly Mattis and Rex Tillerson, were insisting Trump recertify at the next deadline, in July. Trump was resistant but acquiesced to the pleas of his team to allow them to finish crafting a new interagency strategy on Iran. On July 13, my colleague Stephen F. Hayes and I reported in The Weekly Standard that Trump would recertify the deal a second time.

But four days later, on the day of the deadline, an article by Bolton in the Hill made its way to Trump via Iran-deal opponent and White House aide Steve Bannon. The headline read: “Trump Must Withdraw from the Iran Nuclear Deal—Now.” In his op-ed, Bolton argued that Trump “should stop reviewing and start deciding” how to exit the deal. For several hours that day, according to reporting by Hayes and me, Trump reversed his decision to recertify the deal. The White House team scrambled to roll out a brand-new policy. In one meeting that day with his national security team, Trump called up Senator Tom Cotton and placed him on speakerphone as Cotton made the case against recertification.

In a final meeting in the late afternoon, Tillerson and national security adviser H.R. McMaster prevailed on Trump to follow through on the plan to recertify, at least once more. Trump eventually assented, but not before vowing it would be the last time he would do so. It was: Trump did not recertify in October 2017 and, in May 2018, pulled the United States out of the agreement. Bolton and Cotton, working from the outside, won.

This may be the most difficult tactic for Pelosi, who so far has been unable to demonstrate she has Trump’s trust or respect—something the outside voices have always been able to draw on. She’s not

• one of Trump’s old business friends in New York,
• a consistent defender in the conservative media,
• or a former campaign or White House aide.

The best way for Pelosi to persuade Trump from the outside is to do perhaps the unthinkable for a liberal Democrat from San Francisco: Go on Fox News. A lot. Pelosi or her deputies won’t be the obvious choices for the booking producers at Fox & Friends and Hannity, but House Democrats would be wise to take every opportunity to speak directly to Trump on his favorite cable network. A few solid appearances on Fox News Sunday, for instance, would help Pelosi immensely.

Pelosi herself already seems to recognize the necessity of making a public case, most obviously on television, for compromise with Trump. “You know how I talk to him?” she told Draper. “I just say it in public. That’s what he hears: what people say in public.” A Democrat in Trump’s Washington could do worse.