Across the room, an unlikely group of allies tried to persuade him to join them. His son-in-law, Jared Kushner -- the driving force behind the effort -- had invited the liberal commentator and former Obama administration official Van Jones and celebrity Kim Kardashian West to the White House for an impromptu meeting.
But first they had to deal with one problem that had been bothering the President for weeks: Willie Horton.
Horton, a convicted murderer who raped a woman after he was granted a weekend furlough from prison in Massachusetts, was the subject of a withering 1988 presidential campaign ad attacking the Democratic nominee, Michael Dukakis, the Massachusetts governor at the time. The ad, which exploited racist stereotypes, was devastating to Dukakis, and Trump was worried that he could suffer his own Willie Horton moment in 2020 if he backed the bill -- a fear stoked by Sen. Tom Cotton, an Arkansas Republican and chief congressional opponent of the effort.
"He was afraid," Jones said of the President. "He was concerned someone would get out, hurt someone and that would be the end of his political career."
Jones, a CNN host and commentator, and Kardashian West sought to imprint the name of another convicted felon in Trump's mind: Alice Marie Johnson, a 63-year-old woman who had been serving a life sentence for money laundering and a nonviolent drug offense until Trump granted her clemency in June to broad acclaim. Every time Trump mentioned Horton, Jones and Kardashian West reminded him of Johnson.
"We just kind of circled back, Van and I, in talking to the President to explain: But you have Alice now, and Alice is your legacy," Kardashian West, who had helped convince Trump last spring to commute Johnson's sentence, told CNN. "She really opened up his heart and his eyes."
The half-hour meeting was just one of several pivotal moments that ultimately led Trump to endorse a groundbreaking prison and sentencing overhaul bill last month, ramping up pressure on a reluctant Senate Majority Leader Mitch McConnell -- who has doomed similar efforts in the past -- to bring it to the floor for a vote.
On Tuesday night, the Senate passed the bill 87 to 12. Trump is expected to sign it this week before leaving for his Mar-a-Lago resort. The effort cements what is so far the biggest bipartisan victory of his presidency and turns the page on decades of policies that critics say were brutal, racist, ineffective and costly.
The timing is particularly noteworthy given that it comes as nearly every aspect of the President's political and business life is under investigation, and substantive congressional policy making has practically ground to a halt.
The bill's passage is also a win for Kushner, whom the bill's supporters credit with working behind the scenes to steer the legislation past significant opposition within the Trump administration and past shifting coalitions on Capitol Hill.
This story, based on interviews with more than a dozen administration officials, members of Congress, and advocates and opponents of the legislation, tracks the winding journey to push the bill, known as the First Step Act, through Congress to the desk of a President who campaigned on the promise of renewing tough-on-crime policies.
At times the bill seemed poised to fail. Yet at crucial moments a surprising political alliance emerged to keep it alive, one made up of social progressives, black Democrats, members of the religious right, fiscal conservatives and libertarians. The effort has proved so resilient this time around, opponents have dubbed the First Step Act the "zombie bill" for its refusal to die.
Under the legislation, thousands of federal inmates will be able to leave prison earlier than they otherwise would have. Many could secure an earlier release thanks to new credits awarded for good behavior or through participation in rehabilitation programs. The bill also eases some mandatory minimum sentences, gives judges more leeway to eschew certain sentencing guidelines and eliminates "stacking" provisions that leave offenders serving consecutive sentences for crimes committed with firearms.
"If this bill is the only step Congress takes, it will leave the important work of criminal justice reform substantially undone," said Ames C. Grawert, a senior counsel at the Brennan Center for Justice. "But as a real 'first step,' the bill both changes the conversation -- focusing on how we reduce federal prison sentences, not whether we do it at all -- and offers a real, immediate benefit for currently incarcerated people."
A Democratic blockade
Rep. Hakeem Jeffries didn't want to be seen at the White House.
The New York Democrat represents parts of Brooklyn, one of the most anti-Trump districts in the country, and he was wary about the message his presence at the White House would send. So in the spring, when Kushner asked Jeffries to meet him at his office in the West Wing, he and Rep. Cedric Richmond, the Louisiana Democrat who's the chair of the Congressional Black Caucus, refused. Instead, on March 22, Kushner came to them on Capitol Hill for breakfast. Jeffries, who had been working with Richmond on overhauling the criminal justice system for years, saw it as an early sign that Kushner was serious about the issue.
Still, there was deep skepticism among Democrats. Many were averse to delivering Trump a win, and felt that simply being on the same side of an issue as the President was politically dangerous, particularly given his heated rhetoric over policing and inner city crime.
In 2016, Trump repeatedly spoke about bringing back controversial police practices, like stop and frisk, that disproportionately impact black and Latino men. When Rep. John Lewis, a Georgia Democrat, said he would boycott Trump's inauguration in 2017, Trump tweeted in response that the civil rights icon "should finally focus on the burning and crime infested inner-cities of the U.S."
But over months of meetings and calls with Kushner, Jeffries warmed to the idea that a criminal justice overhaul might be feasible under Trump. He found Kushner to be "authentically committed" and spent time talking with the President's son-in-law about the personal connection he had to the issue.
Kushner's father, Charles, served 14 months in federal prison after pleading guilty to charges of tax evasion, witness tampering and illegal campaign contributions. Jeffries also found a willing cosponsor across the aisle in Republican Rep. Doug Collins of Georgia, a pastor who had seen his state's criminal justice overhaul efforts work to reduce recidivism rates.
Yet a difficult path lay ahead. First, Jeffries had to deal with critics in his own party.
On May 17, the Collins-Jeffries bill drew a fiery rebuke from some of the most prominent members of the Democratic Party, including Sens. Dick Durbin of Illinois, Kamala Harris of California and Cory Booker of New Jersey. The trio wrote a letter laying out the bill's faults as they saw them, including its lack of any sentencing revisions. The American Civil Liberties Union, the NAACP and other progressive groups opposed the bill.
Kushner offered to get involved but Jeffries insisted on handling it himself, according to Jones. In a day, Jeffries and his staffers wrote a point-by-point rebuttal to that letter while listening to the title tracks of one of the most famous rap battles, Jay-Z's "Takeover" and Nas' "Ether." As they worked, Jeffries blasted the music on speakers in his office, according to an aide.
The next week, Jeffries stood up in a private House Democratic caucus meeting to defend his bill from the opposition of House Judiciary Committee ranking member Jerry Nadler of New York, former Attorney General Eric Holder and other powerful Democrats. "What I recall is that Rep. Jeffries knew the bill in depth; answered questions fully; and removed the doubts of some completely," said Democratic Rep. Anna Eshoo of California.
A few days later, the bill passed the House with 360 votes, including nearly 70% of the House Democratic caucus and almost every Republican voting in favor of it.
"It's clear that some elements on the hard-left unleashed everything, including the kitchen sink, to try to stop the criminal justice reform effort in the House based on the worldview of all or nothing," Jeffries told CNN. "In the House, we took the position that in order to break the back of the prison industrial complex we needed to begin with a significant, robust bipartisan effort around prison reform that could lay the foundation to get something done."
Administration opposition
As Jeffries was dealing with skeptical Democrats, Kushner was fighting with Republican opponents in the Trump administration, most notably then-Attorney General Jeff Sessions.
In initial drafts, Sessions and his aides at the Justice Department worked to insert provisions that advocates of the bill considered "poison pills," including introducing a new mandatory minimum sentence -- drawing uproar from Kushner's new Democratic partners, who questioned whether the political risk of associating with the White House would be worth it.
"Jared and others at the White House who were working on this went to bat for us," said Jessica Jackson Sloan, who along with Jones co-founded #Cut50, a group that advocates for reducing incarceration in the US. "Jared said, 'I'm going to make sure this is right and I'm not going to let this crap happen again.' "
"That was huge," Jones said.
Within weeks, Jones returned the favor by appearing alongside Kushner at a May 18 White House event focused on the prison legislation. Just walking into the Trump White House, Jones said, felt like "political suicide." He and others who appeared onstage were assailed as "Uncle Toms" on social media.
"They didn't really understand why we were going," said Topeka Sam, a former felon who attended the White House event. "The way we looked at it was, it's our house and despite who's in there, it's our country. And if we're looking to change what's happening to our people that are incarcerated, that we need to be at the table."
But the event offered proof of the bipartisan union that was coming together -- with left- and right-leaning advocates in attendance. It was also an indication that Trump was edging in favor of the bill.
Seated in the front row of the gold-trimmed East Room, Mark Holden, senior vice president of Koch Industries, which has long advocated for criminal justice revisions, watched as Trump strayed from the teleprompter to make an off-script point about how a friend had hired some former prisoners who had turned out to be "superstars." "They would have never gotten the chance," said Trump.
To Holden and several administration officials, the riff was a sign that Trump wasn't just going through the motions. He was in. It was also a notable affront to Sessions, who was also seated in the front row.
Around the time of the event, Sessions attended a meeting at the White House with Trump, Kushner and Energy Secretary Rick Perry -- another longtime advocate of criminal justice revisions. Sessions came armed with a memorandum laying out his arguments against the bill. But he didn't get far before Trump shut him down, according to two sources familiar with the meeting.
It didn't help that by then, Sessions had become a regular target of Trump's ire over his recusal from the Russia investigation. The mere fact that Sessions opposed the effort was almost enough to make the President support it.
"Trump liked the idea of overruling Sessions," said one person familiar with the matter.
After getting his hair cut at the Senate barbershop Tuesday, Sessions declined to talk to CNN about the First Step Act on the record.
August setback
By August, momentum was building behind the bill.
Early that month, the President huddled at his Bedminster golf club with a group of Republican governors supportive of a criminal justice overhaul. There -- as he would in the Oval Office a month later -- Trump raised his concerns that he could face a Willie Horton moment of his own if he backed a bill that would grant early release to some convicted felons. The governors, a senior administration official said, helped assuage Trump's concern and pointed him to the benefit of sentencing overhauls in their states.
But then -- just as supporters of the bill expected a presidential endorsement was afoot -- Sen. Tom Cotton, an Arkansas Republican, managed to get face time with Trump while he was at the White House, reviving the President's fears of Horton and reminding him of the political danger of endorsing the bill. That same day, McConnell told Trump the prison overhaul bill was too divisive among Republicans to bring to a vote before the midterm elections, multiple sources familiar with the call told CNN.
Under pressure, Trump agreed to table the issue until after the midterms.
"At that point, we thought everything had died," said Jones.
Kushner extracted a promise from McConnell to bring the bill to a vote after the midterms if a whip count showed they had the votes. The delay gave supporters a chance to regroup and expand their coalition. Kushner began calling Sen. Mike Lee of Utah so frequently that when he interrupted Lee's family dinner during a vacation in Canada, they knew who it was. "My family said, 'Oh it's Jared, isn't it?' " Lee recalled.
To gain the backing of law enforcement groups such as the Fraternal Order of Police, and National District Attorneys Associations, supporters offered a few key concessions, including one that excludes people convicted of certain fentanyl-related offenses from being eligible for early release. That helped undercut the position of Cotton and other opponents, and positioned Kushner to present a strengthened bill to the President.
McConnell boxed in
On November 14, Trump delivered his endorsement in the White House Roosevelt Room, giving shout-outs to a number of Republican senators who wrote the revised bill -- Chuck Grassley, Lindsey Graham, Lee, Tim Scott, Rand Paul -- and Rep. Collins, an original co-author.
By then, most Senate Democrats had also jumped on board after some key sentencing provisions were added, including one that Senate Democratic Whip Durbin fought for in 2010 that reduced the disparity between sentences for powder vs. crack cocaine. The new legislation will apply that change retroactively to about 2,600 inmates who had been convicted under the previous statute.
There was still just one problem: McConnell was dragging his feet. The day after Trump gave his endorsement, the Senate majority leader told Trump in the Oval Office that he would not bring the measure up for a vote until next year, two administration officials said, pushing the careful compromise into the pit of divided government just as Democrats regain control of the House. Advocates were worried that decision could kill the bill, just as McConnell's reluctance to bring up a previous Senate bill sponsored by his whip, Sen. John Cornyn, and others stifled another effort at the end of the Obama administration.
Kushner and his allies began to ramp up pressure on McConnell. Conservatives flooded his office with calls, including thousands organized by the conservative grassroots group FreedomWorks, which also mounted a pressure campaign in Senate Majority Whip John Cornyn's home state of Texas.
McConnell needed to "hear from everyone who matters to him and that the cost to him of not doing this was going to be greater" than moving forward, a senior administration official said.
Even Trump put on the pressure, urging McConnell several times over the phone to bring the bill to the floor. And while some urged the President to attack McConnell on Twitter, Kushner convinced him to hold his fire, trusting McConnell would ultimately relent.
Lee unleashed
By the end of the month, Cornyn's office was telling the White House they didn't have the votes, claiming support for the bill was softer than it appeared, two sources familiar with the matter said.
Even after Vice President Mike Pence and members of the White House legislative affairs team did their own whip count and concluded they had over 60 votes, McConnell still wouldn't commit to bringing the bill to a vote before the end of the year. So Lee went into overdrive, lobbying his fellow senators day and night, by phone, by text, in person on the Senate floor, at lunch in the Senate cafeteria. "I went nuts," Lee told CNN.
A pivotal moment came when Lee's friend, the conservative Republican Sen. Ted Cruz of Texas, signed on after they added certain provisions that would make it harder for some offenders to get an early release. Cruz was number "29 or 30" in Lee's mind -- more than enough to get the bill up for a vote and easily pass the Senate.
On December 10, Darrell Scott, a black pastor and early Trump supporter, warned McConnell's legal counsel that he would send hundreds of black pastors and activists -- in his words, "500 angry black people" -- to the Senate majority leader's office if he didn't take action.
That evening, Kushner made his most public push yet, appearing on Trump's favorite show -- "Hannity" on Fox News -- to plug the bill.
The next day, McConnell announced he would put the bill on the floor at the request of the President. Scott called McConnell to shower him with praise.
"I told him, 'We're going to build statues of you in the hood,' " Scott recalled.
A week later, on the day the bill passed the Senate, Jones and Kushner had an early-morning phone call to coordinate their efforts.
"The next 48 hours are critical," Jones jokingly told Kushner, echoing a phrase he had heard from Kushner at the end of nearly every one of their calls.
But the goal line was actually much closer, Kushner replied. "I actually think it's only the next 12," he said.
CLARIFICATION: This story has been updated to reflect that Freedomworks is no longer associated with the Koch family.
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