In early July, former President Donald J. Trump received a somewhat unlikely visitor at his golf club and estate in Bedminster, N.J.: Michael Harris, the founder of Death Row Records, who had been imprisoned for drug trafficking and attempted murder, came to meet privately with the man who had pardoned him.
Mr. Harris was connected to the former president by Mr. Trump’s son-in-law, Jared Kushner, and daughter Ivanka Trump, who had helped push him as a pardon candidate, according to two people familiar with the process. The couple were staying at Mr. Trump’s club at Bedminster when the meeting took place, and Mr. Kushner joined, two people briefed on the matter said.
But their lunch served another purpose for some people close to Mr. Trump: Mr. Harris is the type of high-profile Black celebrity that some Trump associates hope will next year highlight the former president’s signature criminal justice reform law, the First Step Act, which was one of Mr. Kushner’s key priorities during his time as an adviser in the White House.
Although Mr. Harris is not a beneficiary of the sentencing law, having received his pardon on Mr. Trump’s last full day in office after serving decades in prison as part of a series of clemency grants, he has nonetheless become an evangelist for it.
Mr. Trump, who has shown gains among Black voters in some recent polls, is hoping to win a slightly larger margin than he has in the past, with the potential to swing key states. He has been indicted four times, a fact that his advisers and allies insist — without offering any evidence — will somehow be helpful with Black voters because he asserts that he’s a victim of overzealous prosecution. (He has also repeatedly called the three Black prosecutors investigating him “racist.”)
But some of his closest allies who have been trying to impress on him the value of boasting his own record on the issue insist that he has absorbed their message, though it is unclear whether that’s true or more of a projection of their own wishes.
Mr. Harris declined to discuss what took place in their meeting, but he expressed gratitude toward the Trump administration in a statement and praised the sentencing law. “The passing of the First Step Act and similar initiatives surrounding” criminal justice reform “has provided much needed relief for so many deserving individuals and families,” he said.
An aide to Mr. Kushner and a spokesman for Mr. Trump did not respond to requests for comment.
Not everyone around the former president believes that he should highlight the First Step Act, which Mr. Trump himself soured on soon after signing it. Mr. Trump, who is often influenced by what he thinks his core voters want, felt affirmed in that view after a number of hard-core Republicans began to criticize it in 2021 and 2022 amid a rise in crime. Some of his conservative associates, who see the bill as problematic with Republicans, said privately that they were unhappy that he had met with Mr. Harris.
While the issue poses a potential challenge for Mr. Trump’s team, the discussions also underscore a broader challenge for President Biden’s team heading into 2024: how to pin down an opponent who has a four-year record as well as decades’ worth of statements on almost every issue that are contradictory.
Mr. Trump has a long history of making racist statements, including attacking a judge’s Mexican heritage; calling for the death penalty for the teenagers who were arrested and later coerced into giving confessions in a case of brutal rape in Central Park in 1989; telling a group of congresswomen of color — almost all of whom were born in the United States — to go back to their countries; and, perhaps most famously, insisting that the first Black president might not have been born in the United States.
He has also grown increasingly violent in his rhetoric about crime in America, saying that he admires the freedom that despots have to execute drug dealers and that shoplifters should be shot on the spot.
At the same time, he has made clear that he viewed the law, which, among other things, sought to reduce mandatory minimum sentences for some crimes, as something that should have won him support from Black voters.
“Did it for African Americans,” he wrote to this reporter for a book in 2022 when asked about his repeated expressions of regret about the law. “Nobody else could have gotten it done. Got zero credit.”
But the Democratic coalition of Black, Latino and younger voters has frayed since Mr. Biden’s victory, with Mr. Trump picking up support from those groups. And one difficulty in holding Mr. Trump to account is that he often has a contradictory set of words and actions that different people can latch onto.
And the bipartisan First Step Act, which Mr. Trump signed in December 2018, is one part of his record that some of his allies believe they can use in 2024 to downplay his strongman rhetoric and actions around race and violence.
“Trump was both bloodthirsty in his rhetoric but signed the First Step Act, which was significant sentencing reform,” said Michael Waldman, the president and chief executive of the Brennan Center for Justice, who also served in the White House during Bill Clinton’s presidency. “Whether he truly believed in it or not, he did it.”
While Gov. Ron DeSantis, Republican of Florida, attacked Mr. Trump over the law, calling it a “jailbreak” bill despite voting for an early version of it, his criticisms didn’t dent Mr. Trump’s support. And Republican criticisms of the law have become more muted as the party has coalesced around him.
Both praising the legislation and making racist statements would be in keeping with Mr. Trump’s 2016 campaign, which was a mix of demagoguing immigrants and small-time criminals, using law-and-order rhetoric, and accusing Hillary Clinton of racism against Black men.
It is also far from the only issue on which Mr. Trump has decades of action and statements he can point to that allow different people to read what they want into his behavior, and will happily play to whatever audience he’s in front of.
Other than Senator Mitch McConnell of Kentucky, the Republican majority leader, no person is more responsible than Mr. Trump, who gave the Supreme Court its 6-3 conservative majority, for overturning the landmark decision that recognized abortion rights as constitutionally protected. Yet, Mr. Trump called a six-week abortion ban signed by Mr. DeSantis a “terrible mistake,” and has refused to be specific about a national ban. That has alarmed Democrats, who worry he will try to appear moderate on the issue in a general election race against Mr. Biden.
More recently, some of Mr. Biden’s allies watched angrily as the Spanish-language network Univision, which Mr. Trump has attacked in the past but now has new ownership, gave the former president a relatively soft interview, one that Mr. Kushner arranged, and minimized pushback from Mr. Biden’s team.
It remains to be seen how willing Mr. Trump will be, if at all, to speak about the criminal justice law, or whether Mr. Harris might be asked to speak publicly.
The same week that Mr. Harris met with Mr. Trump, the former president received a call from Alice Johnson, whose life sentence on charges related to cocaine possession and money laundering was commuted after a meeting between Mr. Trump and the celebrity Kim Kardashian. Ms. Johnson was the person who recommended to Mr. Kushner and Ms. Trump that Mr. Harris be granted clemency.
“My whole conversation was just encouragement” about the criminal justice reform bill, said Ms. Johnson, who spoke at the Republican National Convention in 2020 and was pardoned by Mr. Trump a short time later. She said no one had asked her to call him or engage in politics for him next year. But, she added, “he actually is proud of that piece of legislation.”