In late October, just days before the presidential election, and almost a year after federal authorities had seized a handgun from his private plane, the rapper Lil Wayne spent nearly an hour with Donald J. Trump at the president’s Doral Golf Club in Miami.
The two men discussed Lil Wayne’s upbringing in New Orleans and his budding interest in criminal justice reform, according to Bradford Cohen, a South Florida lawyer who was present and set up the meeting.
“I think they had a very strong connection,” Mr. Cohen, who competed on Mr. Trump’s TV show “The Apprentice” in 2004, said.
The encounter culminated in a smiley, thumbs-up photo-op that the rapper then posted on Twitter — an endorsement that came as Mr. Trump’s re-election campaign was working to improve his standing with Black voters, though he had often vilified Black people and frequently sought to divide the country along racial lines. The support from a largely apolitical artist was met with backlash from some fans.
That sentencing will never come. Early Wednesday, Lil Wayne found himself among the 143 pardons and commutations announced by former President Trump during his final hours in office. He joined three other figures from the hip-hop universe, including the Florida rapper Kodak Black, another client of Mr. Cohen’s; Desiree Perez, the chief executive of Jay-Z’s Roc Nation; and Michael Harris, known as Harry-O, a founder of Death Row Records who has been in prison for 30 years.
The clemency decisions capped a complex, symbiotic and often controversial relationship between Mr. Trump and rap that dates back to the 1990s, when the businessman was a frequent clubgoer and lyrical motif representing wealth and flash.
“He’s in the entertainment world,” Mr. Cohen said of the former president in an interview on Wednesday. “He’s got a style that’s similar in terms of the way that he carries himself, and a lot of rappers and people in the industry relate to that.”
Mr. Cohen said that Lil Wayne’s looming gun charge, which had been under investigation for nearly a year, was not the reason for his pre-election summit or support for Mr. Trump. But he acknowledged that it may have ultimately been a factor in the pardon decision, as thousands lobbied for last-minute clemency.
“It never hurts that someone gets a full understanding of an individual when they’re just looking at a piece of paper,” he said. “In hindsight, I guess it worked out.”
Lil Wayne, 38 and born Dwayne Michael Carter Jr., is widely considered one of the most successful and influential hip-hop artists of his generation. But aside from a song criticizing George W. Bush for his handling of Hurricane Katrina, he had typically avoided politics altogether, distancing himself from partisanship and the Black Lives Matter movement. Asked about Mr. Trump before the 2016 election, Lil Wayne laughed and responded, “Who’s that?”
The gun charge stemmed from a search of his private plane upon landing in the Miami area on Dec. 23, 2019, when authorities found a gold-plated .45-caliber Glock handgun and ammunition, along with a cache of drugs (for which no one was charged) and nearly $26,000 in cash. Lil Wayne was unable to legally carry a firearm, having previously pleaded guilty to felony gun possession in New York in 2009; he had served eight months at Rikers Island.
Howard Srebnick, a lawyer who represented Lil Wayne in the criminal case last year, said in a statement on Wednesday: “A pardon for Mr. Carter is consistent with the views of many jurists — including Supreme Court Justice Amy Coney Barrett — that prosecuting a nonviolent citizen for merely possessing a firearm violates the Second Amendment to the U.S. Constitution.”
He added, “The gold-plated firearm, which Mr. Carter never operated, is a collector’s piece, given to him as a Father’s Day gift.”
Lil Wayne’s application for a pardon was supported in letters by Deion Sanders, the N.F.L. Hall of Famer, and Brett Berish, the chief executive of a sparkling wine brand, according to the White House, which also highlighted the rapper’s charitable giving.
Mr. Cohen said he had started the application process for a pardon right after Lil Wayne was charged in November, and that the rapper was “thrilled” with the president’s decision. Through representatives, Lil Wayne declined to comment.
Mr. Cohen — whose connection to the Trump orbit also included representing the president’s former campaign manager Corey Lewandowski — led the advocacy for Kodak Black, as well. Black, whose legal name is Bill Kapri (born Dieuson Octave), was granted a commutation, which will forgive the remainder of his 46-month sentence for lying on background paperwork while attempting to buy guns. He has served nearly half of that time, and could be released from a federal prison outside of Chicago as soon as Wednesday, Mr. Cohen said.
While many paid thousands of dollars to lobby for clemency, Mr. Cohen said he instead relied on a monthslong social media and letter-writing campaign, recruiting notable figures like Lamar Jackson of the Baltimore Ravens and the former New York Police Department commissioner Bernie Kerik to vouch for Black’s character and philanthropy.
“Our route was less conventional. We had supporters like Gucci Mane and Lil Yachty and Vanilla Ice,” Cohen said. “We did everything that we could to get eyes on it.”
President Trump has discussed potential pardons that could test the boundaries of his constitutional power to nullify criminal liability. Here’s some clarity on his ability to pardon.
- May a president issue prospective pardons before any charges or conviction? Yes. In Ex parte Garland, an 1866 case involving a former Confederate senator who had been pardoned by President Andrew Johnson, the Supreme Court said the pardon power “extends to every offense known to the law, and may be exercised at any time after its commission, either before legal proceedings are taken or during their pendency, or after conviction and judgment.” It is unusual for a president to issue a prospective pardon before any charges are filed, but there are examples, perhaps most famously President Gerald R. Ford’s pardon in 1974 of Richard M. Nixon to prevent him from being prosecuted after the Watergate scandal.
- May a president pardon his relatives and close allies? Yes. The Constitution does not bar pardons that raise the appearance of self-interest or a conflict of interest, even if they may provoke a political backlash and public shaming. In 2000, shortly before leaving office, President Bill Clinton issued a slew of controversial pardons, including to his half brother, Roger Clinton, over a 1985 cocaine conviction for which he had served about a year in prison, and to Susan H. McDougal, a onetime Clinton business partner who had been jailed as part of the Whitewater investigation.
- May a president issue a general pardon? This is unclear. Usually, pardons are written in a way that specifically describes which crimes or sets of activities they apply to. There is little precedent laying out the degree to which a pardon can be used to instead foreclose criminal liability for anything and everything.
- May a president pardon himself? This is unclear. There is no definitive answer because no president has ever tried to pardon himself and then faced prosecution anyway. As a result, there has never been a case which gave the Supreme Court a chance to resolve the question. In the absence of any controlling precedent, legal thinkers are divided about the matter.
- Find more answers here.
Kodak Black remains under indictment on charges of criminal sexual conduct in South Carolina from 2016, although a trial has been repeatedly delayed. He faces up to 30 years in prison if convicted.
Boldfaced names may have helped in the cases of the other hip-hop world commutations, too. Snoop Dogg reportedly lobbied on behalf of Mr. Harris, or Harry-O, an early financial backer of his former label, Death Row Records, which helped bring gangster rap to the mainstream. Mr. Harris, 59, had his sentence for conspiracy to commit first-degree murder commuted by the president after serving three decades of a 25 year-to-life punishment.
Snoop Dogg worked alongside the reform advocate Alice Johnson, who was herself pardoned by Trump last year, following a campaign by Kim Kardashian West and others. “They did some great work while they was in there and they did some great work on their way out,” Snoop Dogg, once a vocal critic of Trump, said of the administration upon hearing the news, according to The New York Post.
A longtime associate of Jay-Z, Desiree Perez, 52, woke up this morning at 5 a.m. to a phone full of text messages letting her know that her pardon had been granted. Now the chief executive of Roc Nation, the management company and label with a social-justice component, she was convicted in 1994 of conspiracy, with intent to distribute drugs. Ms. Perez said she had applied for the pardon just two days earlier, after seeing news reports of Mr. Trump’s plans for his final hours in office.
“I feel good, but a little numb,” Ms. Perez said in a phone interview. “I haven’t forgiven myself and I’m not sure I ever will.”
Ms. Perez works closely with the N.F.L. in its partnership with Jay-Z, and the White House called her “an advocate for criminal justice reform in her community.”
“There is so much judgment that goes along with a conviction without the time and reflection from others about, ‘How did someone end up in that place?’ My story has a reason,” Ms. Perez said. “Everyone’s story has a reason. I’m just a girl from the Bronx, and to think about all the things I had to overcome and how I persevered to get where I am, well, now you’re making me cry.”
But asked for her personal feelings about Mr. Trump, Ms. Perez deflected. “I would prefer not to answer that question today,” she said. “It’s not the best etiquette.”
Katie Rosman contributed reporting.