“Frankly, We Did Win This Election”: The Inside Story of How Trump Lost

by Michael C. Bender

  Trump refused to condemn the violence, partly because he thought it would invite criticism that he was weak. Experts expected that he would pay a political price for failing to soften his tone. It may have limited his reach, but it never caused the floor to drop. Ten days before the Fayetteville rally, Trump had refused to condemn former Ku Klux Klan leader David Duke. Mitt Romney, the 2012 Republican presidential nominee, reproached him for “disgusting and disqualifying” comments about the KKK, Muslims, and Mexicans. Nearly 100 Republican national security experts denounced him in an open letter over “his hateful, anti-Muslim rhetoric” and “embrace of the expansive use of torture.”

  None of that mattered to primary voters. They seemed to interpret the attacks as proof of Trump’s outsider status. During that same ten days, Trump won seven of the eleven Super Tuesday state primaries, convinced Ben Carson—a Black Republican pediatric neurosurgeon—to drop out of the race and back his campaign, and collected an endorsement from Alabama’s Jeff Sessions, the first sitting U.S. senator to back him.

  “In this race for the White House,” Trump declared at the Republican convention that year in Cleveland, “I am the law-and-order candidate.”

  But as soon as Trump arrived in the White House, Jared went to work sanding down his father-in-law’s hard edge with a push to soften prison sentencing guidelines. It was a jarring contrast with the unforgiving strongman image that the newly sworn-in president had feverishly protected. But the issue was personal for Jared. His own father had spent fourteen months in a federal prison.

  Jared was four years old in 1985 when his father was put in charge of Kushner Companies, the family’s New Jersey real estate company. Over the next two decades, the company accumulated more than 25,000 apartments, thousands of acres of land, and millions of square feet of commercial real estate. Charlie Kushner became a boldfaced name in state and national politics, wining and dining with Bill Clinton, Al Gore, and Bibi Netanyahu. In 2002, Charlie Kushner was the single largest donor for New Jersey governor Jim McGreevey, who rewarded his financier by nominating him chairman of the Port Authority of New York and New Jersey, a powerful position in charge of hundreds of millions of dollars in development contracts. But Charlie Kushner had to withdraw from consideration as McGreevey was consumed by a controversy that involved cheating on his wife with a man to whom he’d given a cushy government job. McGreevey’s paramour, an Israeli national with a work permit, had been sponsored by Charlie Kushner, who had also put him on the family company’s payroll as a favor to McGreevey.

  Kushner family ties frayed, too. Legal disputes and bickering with his siblings reached the point in December 2003 that Charlie Kushner hatched a plot for a prostitute to lure his brother-in-law to the Red Bull Motor Inn on U.S. 22 in Bridgewater, New Jersey. The plan worked, and Charlie mailed the incriminating videotape to his sister. But a private investigator he had hired to help with the scheme double-crossed him and cooperated with the FBI.

  The prosecution was led by an ambitious young U.S. attorney in New Jersey named Chris Christie, and Charlie Kushner ultimately pleaded guilty to sixteen counts of tax evasion, one count of witness tampering, and another count of making illegal campaign donations. He was sentenced to two years in federal prison and released after fourteen months at Federal Prison Camp, a minimum-security jail in Montgomery, Alabama. Jared visited him nearly every weekend.

  “This is a great victory for the people of New Jersey,” Christie said after the sentencing. “No matter how rich and powerful any person may be, they will be held accountable for criminal conduct by this office.”

  For Jared, the lesson was that prison sentences were too stiff.

  The new administration was barely two months old when Jared held his first meeting at the U.S. Capitol on criminal justice reform. Jared wanted to revive a proposal to reduce mandatory prison sentences that had failed the year before due to opposition led by U.S. senator Jeff Sessions. Sessions, who was now Trump’s freshly confirmed attorney general, didn’t know about Jared’s meeting—Sessions had been preparing for a speech the next day in St. Louis, where he would blame “viral videos” for the tense relationship between law enforcement and minority communities and lay the ground work for his aggressive prosecution of drug offenders.

  The striking discrepancy between Jared and the rest of the administration received little attention at the time. When it came to Jared, the story focused on the vast gap between his expansive White House portfolio and his limited amount of relevant experience. Both the Washington establishment and his colleagues in the White House derisively referred to him as “the princeling.”

  But that was how Jared operated. In a 2015 interview with Forbes magazine for its “40 under 40” issue, Jared refused to be defined by the real estate company he was running. Asked about Kushner Companies, he instead pointed out that he had bought a newspaper, the New York Observer, and ruminated about his interest in expanding broadband Internet access. He spoke about “creating cultures of results instead of cultures of seniority” and how he could apply that philosophy to any company.

  “Every business I do and every transaction I’m involved with teaches me and makes me better in all the other businesses that I’m in,” Kushner told Forbes.

  In the White House, Jared was brokering Middle East peace and would take the lead on U.S. relations with Canada, Mexico, and China. He would oversee issues related to veterans’ health care. And he spoke broadly and optimistically about plans to transform the federal government into something smooth, sleek, and corporate. That push to streamline government started by creating a new layer of bureaucracy: the Office of American Innovation.

  The new office grew out of an idea that Bannon, as the White House chief strategist, had called the Strategic Initiatives Group, which he had pitched as a McKinsey-style consultancy inside the West Wing to push Trump’s campaign promises into law. Jared liked the idea and added his input. He asked for help from Chris Liddell, a former Microsoft and General Motors executive who had joined the administration. Liddell wasn’t entirely sure what the new group was supposed to do, so he went and found Bannon’s aide, Andy Surabian.

  “Did Steve explain to you what this group is doing?” Liddell asked him.

  “No,” Surabian said. “Not in much detail.”

  “Dammit,” Liddell replied. “I was hoping you could tell me.”

  The group’s early meetings were in Bannon’s office, but Jared packed the room with his own loyalists, including Reed Cordish, a Princeton tennis player who parlayed his friendship with Jared and Ivanka into a gig in the West Wing. White House staff chief Reince Priebus panicked that none of his people were included in the meetings and sent his deputy, Katie Walsh. The only senior White House official not present seemed to be Stephen Miller, even though he was always invited to the group’s standing 7:30 a.m. meeting. Miller’s friends and critics called him many things during the next four years, but a morning person was never one of them.

  In the second week of the new administration, a memo circulated inside the West Wing to frame the ambitious new effort, but it also signaled the disorganization that would doom most of the president’s policymaking attempts over the next four years. The five-page memo was authored by three staffers, each of whom reported to different bosses, and included two organizational charts.

  The meetings quickly migrated from brainstorming sessions in Bannon’s office to the Roosevelt Room, where senior aides could schmooze with corporate executives who had started attending at Jared’s urging.

  Jared’s crew floated criminal justice reform, which deflated Bannon’s staffers.

  “Was that even something Trump supported?” one whispered during a meeting.

  Trump’s first test at addressing the country’s racial tensions came in the summer of 2017. On a Saturday in August, thirty-two-year-old Heather Heyer was killed, and nineteen others injured, when a twenty-year-old neo-Nazi drove his souped-up 2010 Dodge Challenger at about 30 miles per hour into a c
rowd in Charlottesville, Virginia. Heyer and the others were protesting a white supremacist rally organized to oppose the removal of a statue of Robert E. Lee, a Virginian who commanded the Confederate States Army during the Civil War.

  Trump had been golfing at his Bedminster club that morning. He planned to sign veterans’ health care legislation that afternoon, and reporters were already scheduled to attend the ceremony in one of the club’s ballrooms. It had been about two hours since Heyer’s death, and Trump said he wanted to “put out a comment as to what’s going on in Charlottesville.”

  “We condemn in the strongest possible terms this egregious display of hatred, bigotry, and violence on many sides—on many sides,” Trump said.

  The White House tried in vain to focus cable networks and newspaper reporters on the first words of his statement instead of the final phrase—“on many sides”—that he’d ad-libbed and then repeated. But the obvious question they couldn’t answer was how the president could put any blame on the peaceful counterprotesters. His remarks seemed to justify the white supremacist violence, and Trump’s silence over the next twenty-four hours unnerved even those around him.

  Back at Trump Tower in New York two days later, one of his few visits back home as president, Trump had a news conference scheduled to discuss the nation’s infrastructure. Hope and Sarah Sanders, the White House press secretary, urged Trump not to take questions. Trump agreed, then he took the elevator down to the lobby, where reporters were waiting, and promptly invited questions after a brief infrastructure statement.

  “If you have any questions, please feel free to ask,” he said.

  Predictably, nearly every question that followed focused on Charlottesville. Trump criticized executives who’d quit his business councils. He defended his controversial statement and even reread his quote—except for the phrase he’d ad-libbed. He lamented the removal of Civil War statues. He disputed that he had support from neo-Nazis. Then, after the news conference, David Duke, the former KKK grand wizard, publicly thanked Trump for his “honor and courage to tell the truth about Charlottesville and condemn the leftist terrorists.”

  At one point, Trump pleaded for an infrastructure question.

  He again blamed the counterprotesters.

  “You had some very bad people in that group, but you also had people that were very fine people, on both sides,” Trump said.

  The next day, Stephen Schwarzman, a longtime friend of Trump’s and chief executive of Blackstone Group, called the president and told him he had disbanded the White House Strategic and Policy Forum. There weren’t enough executives left who would stand by Trump after his repeated failures to adequately address Charlottesville, Schwarzman said. Trump hung up and beat his friend to the punch by quickly tweeting that he was shutting down the panel.

  Gary Cohn, the president’s top economic adviser—and a registered Democrat—was even more despondent. Raised Jewish on the East Side of Cleveland and a longtime New York resident, he stood next to Trump for the infrastructure news conference and grew increasingly alarmed and uncomfortable.

  Later, in a private meeting inside the Oval Office, Cohn unloaded on the president. Cohn told Trump that his lack of clarity had been harmful to the country and that he’d put an incredible amount of pressure on people working in the White House. He told Trump that he might have to quit.

  No one backed Cohn up. Others in the room, including Pence, remained quiet.

  Cohn returned to his office after the meeting broke up. Following a few minutes behind, Pence climbed the flight of stairs and appeared at the threshold of Cohn’s door.

  “I’m proud of you,” Pence told him, safely out of earshot of the president.

  Trump remained skeptical about Jared’s push to change criminal justice laws. Trump worried about upsetting law enforcement groups, whose backing he touted at nearly every campaign rally. He didn’t want to create any space for other conservative politicians to criticize him. In a speech about the opioid crisis in March 2018, Trump mocked blue-ribbon commissions tasked with finding detailed solutions to systemic problems like drug abuse. The problem was drug dealers, Trump said, and the only thing they understood was toughness.

  “That toughness includes the death penalty,” he said.

  Trump was one of the few politicians in the country willing to consider capital punishment for drug dealers. Still, Jared remained undaunted.

  He appealed to Trump as his children’s grandfather and reminded him of his own father’s ordeal. He suggested that addressing the issue would bring new support for Trump from Black voters, and he scheduled meetings with conservative politicians who supported prison reform, including Georgia governor Nathan Deal and Florida attorney general Pam Bondi.

  But the break came when Jared and his allies used Trump’s own language against him and presented it to Trump as if it were another campaign promise kept—even though it was to a pledge he’d never explicitly made.

  “You campaigned that you were going to work for the forgotten men and women of this country,” Reed Cordish told Trump in a private meeting early in the administration. “And there’s nobody more forgotten or underrepresented than people in prison.”

  “That’s right,” Trump said, as if the idea had been his all along. “We’ve got to do something about this.”

  Trump had mobilized his 2016 campaign around the promise to fight for the “forgotten man.” The phrase referred to any worker who felt unfairly treated by a list of imperfect social institutions: government, economic, religious, or otherwise. But it was a generic and pliable rhetorical device that Franklin Delano Roosevelt had most famously invoked during his first presidential campaign in 1932. But where FDR used it to help sell the working class on massive government programs and regulations like Social Security, a minimum wage, and union protections, Trump used it in his bid to dismantle many of those same programs—the “deconstruction of the administrative state,” as Bannon described it.

  Trump told Jared that any criminal justice legislation required support from the police groups that had endorsed him. Then, in May—two months after supporting capital punishment for drug dealers—Trump’s White House hosted its first prison reform summit.

  Even during the summit, Trump signaled he wasn’t fully on board. He veered off the script and threatened to veto a bad bill, even though the effort was led by his own White House. He recalled how he’d had a friend who once hired three felons, one of whom turned out to be “not the greatest” worker. Near the end, Trump openly questioned his own prepared remarks, which made it clear he hadn’t bothered to read the script until it was scrolling through the teleprompter at the event.

  “America is a nation that believes in second chances, and third chances, in some cases, and…” Trump said and then paused as he stared at the teleprompter.

  “I don’t know,” he continued. “I guess even fourth chances? I don’t know about that.”

  Nervous laughter rippled through the room.

  “That’s where I think you and I may differ,” Trump said as he turned to CNN political analyst Van Jones and other prison reform advocates Jared had invited to the event. “You know, we’ll go two or three, but maybe we won’t go that extra length. Okay? You’re a little more liberal in that way, but that’s okay. But we’re both well-intentioned, I can tell you that.”

  Two weeks later, Jared found the final puzzle piece to unlock Trump’s full support: celebrity endorsement.

  At the end of May, Jared and Ivanka enlisted Kim Kardashian, the reality TV star whose rapper husband, Kanye West, had voiced support for Trump after the 2016 election and visited the president-elect in Trump Tower during his transition to the White House. In an Oval Office meeting with Trump, Kardashian lobbied the president to release from prison a woman named Alice Johnson. Johnson had spent two decades behind bars after running a multimillion-dollar cocaine operation with ties to a Colombian drug cartel. Kardashian described her to Trump as a grandmother, a first-time delinquent, and
an offender of a nonviolent crime.

  On June 6, 2018—one week after the meeting with Kardashian and over the objections of White House staff chief John Kelly and White House counsel Don McGahn—Trump granted Johnson clemency. The reelection campaign sent video cameras to record her release from prison. The footage would be turned into Trump’s Super Bowl commercial.

  One of Jared’s top priorities for the campaign was expanding Trump’s share of the Black vote.

  The campaign’s focus group testing showed there was some room to grow with minority voters if the campaign explained Trump’s policies in a positive and carefully tailored way. Brad viewed that as an opportunity, too, and prioritized the campaign’s coalitions department, which was designed to reach out to specific groups of voters, including Black voters, religious voters, and law enforcement officers.

  He hired Hannah Castillo from the White House to oversee the coalition-building, making her one of his top deputies, on par with digital chief Gary Coby, political boss Chris Carr, and communications director Tim Murtaugh. Brad tasked Castillo with building a coalitions department that was effectively a series of mini-campaigns inside the broader reelection effort. The major coalitions—Black voters, Hispanic voters, and women—would each be staffed with their own political strategist, communications director, and chief fundraiser to market Trump in a way that would persuade targeted voters. The campaign also created separate websites—and branded merchandise available for purchase—for a lengthy list of other coalitions: evangelicals, Catholics, Chaldean Catholics, Mormons, “Hindu Voices for Trump,” as well as veterans, lawyers, truckers, and even felons, or, as the coalitions department referred to them, “Second Chance Voters for Trump.”2