Bobby Shmurda Illustration by Andy Friedman

Last spring, a song by a rapper named Bobby Shmurda (given name: Ackquille Pollard) was posted to YouTube. The lyrics were full of violent braggadocio (“I’ma run up, put that gun on ’ em”), and alluded several times to GS9, his Brooklyn rap collective (“Grimey shooters dressed in G-Star”). The song became a hit. Although Shmurda was nineteen and had a discography of one mix tape—he calls them “shmixtapes”—Epic Records signed him to a major contract.

A few months later, a defense attorney named Howard Greenberg (given name: Howard Greenberg) got a call. Shmurda needed counsel. Prosecutors alleged that GS9 was a gang, the G Stone Crips, and that Bobby Shmurda was its “driving force.” In an indictment, handed down in December, Shmurda was charged with gun possession and conspiracy to commit murder, among other things. His associates are charged with close to a hundred more crimes, including murder. “I’ve had lots of high-profile clients,” Greenberg said—Levi Aron, the “butcher of Borough Park”; James Colliton, the “Lolita lawyer”; and “one of the Wu-Tang guys, I think.” He was not familiar with Shmurda’s work—“When I first heard the name, frankly, I thought it was Yiddish”—but he took the case.

Songwriters walk a fine line between fact and poetic license. Art is protected speech. Bob Marley did not actually shoot the sheriff. In 2009, Jay Z rapped that he and President Obama were in touch by text; he later boasted that he “got White House clearance” for a trip to Cuba. “It’s a song,” Jay Carney, then the press secretary, said at a briefing. “The President did not communicate with Jay Z over this trip.”

Still, Shmurda’s lyrics seemed to veer uncomfortably close to the truth. “My music is straight facts,” he told a reporter last year. (He is now on Rikers Island, awaiting trial.)

Greenberg lives in South Jersey, but many of his cases are in Brooklyn. Recently, anticipating snow, he booked a room at a Marriott near the courthouse. “I didn’t want to get jammed up,” he said, ducking into an empty ballroom and taking a seat at a table. He wore a black faux-leather jacket; his hair is shoulder-length and colored in overlapping layers of black, maroon, and natural gray. “At first blush, I might rub people the wrong way,” he said. “But my results speak volumes. There’s no higher calling, by the way, than what I do. Twenty years ago, I heard an angel’s voice, which I can only analogize to Charlton Heston in ‘The Ten Commandments,’ and it said to me, ‘There is no such thing as a dead case!’ And since then I’ve believed that if you look hard enough at any fact pattern, you begin to see reasonable doubt.”

He pounded a fist on the table. “The government hates rap. Not that I’m a fan”—he listens to Roy Orbison—“but I don’t give a shit what you say in your music. ‘I’ve got hos in different area codes.’ ‘I’m gonna bust a cap up your ass.’ It’s all bullshit!”

At a press conference in December, an N.Y.P.D. officer, James Essig, said that Shmurda’s music “pointed us in the right direction,” and that the songs were “almost like a real-life document of what they were doing on the street.” More recently, the special narcotics prosecutor Bridget Brennan said, “Song lyrics play no role in the prosecution’s case and are not part of the evidence.” Still, Greenberg said, “Even if they don’t do it to Bobby, the government has used rappers’ words against them before.”

Last May, in Brooklyn, Ronald Herron was tried for murder and narcotics trafficking. Prosecutors attempted to show that he had a lot in common with Ra Diggs, his rap persona, alleging that Herron was a high-ranking member of a gang called the Murderous Mad Dogs (Ra Diggs: “I’m a Murderous Mad Dog”) who controlled his henchmen by dispensing both carrots and sticks (Ra Diggs: “My generosity givin’ niggas colostomies”).

One of Shmurda’s lyrics is “I been sellin’ crack since, like, the fifth grade.” Last year, a radio host asked him, “Have you really been selling crack since the fifth grade?”

“Yeah,” Shmurda said. Asked about his legal troubles, he said, “I don’t think I should be talking about that on the radio.”

Shmurda recently hired new counsel. Greenberg continues to represent Bobby’s brother, Javase, on related charges. “The record company came in and anointed new lawyers,” Greenberg said. “What Epic Records knows about criminal defense is what you or I know about flying a fucking space shuttle.” Walking out of the Marriott ballroom, he got a call from a client. Greenberg shouted into his flip phone. “Tony? You owe me a thousand dollars, Tony!”

Tony, on speaker, said, “I’m gonna pay you, Howard. I don’t want you to put that white-man voodoo on me.”

They negotiated. “Five hundred dollars, in cash, by Friday, or I’m putting a curse on your ass,” Greenberg said. ♦