The Case Against Bobby Shmurda: Conspiracy Law And GS9 Loyalty : Louder Than A Riot Six years after his arrest, Bobby Shmurda's fans are still anxiously awaiting his return. The rapper ultimately stayed loyal to his crew in court, but the chokehold of conspiracy law also left him with few other options. In our final chapter of Bobby's story, we follow his legal drama: cycling through defense lawyers, being strong-armed by prosecutors and making last-ditch outbursts in court. Finally, we sit down with Bobby in prison as he looks to his future on the other side of his cell.

My Brother's Keeper: Bobby Shmurda (Pt 3)

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A warning before we begin - this podcast is explicit in every way.


Previously on LOUDER THAN A RIOT.


JIMMY FALLON: Please welcome Bobby Shmurda.


MAINO: He was in the street longer than he was famous.

MADDEN: We don't call ourselves no gang members. We a family.

RUDELSIA MCKENZIE: But my son needs justice.

BOBBY SHMURDA: When you get locked up, all the rap shit go out the window. Right now, I'm in jail. And I'm just trying to get home. I'm thinking about my freedom.


CARMICHAEL: There's a song Bobby released about a month before the raid at Quad Studios. It's called "Wipe The Case Away." And if you listen to it now, it feels like a premonition.


BOBBY SHMURDA: (Singing) I told my lawyer I got 40 on me. Is you trying to go to court for me? These [expletive] trying to put a charge on me. Ooh, why they want to lock the doors on me? Why they want to lock the doors? Why they want to put some fraud on me?

MADDEN: Just hours after that Quad Studios raid in December, 2014, that premonition becomes Bobby's reality when he appears in court for the first time alongside his brother Fame and their lawyer.


CARMICHAEL: The court clerk addresses Bobby by his government name, Ackquille Pollard. How do you plead? - the clerk asked him.

MADDEN: Not guilty, Bobby's lawyer responds.

CARMICHAEL: Then the prosecutor says, there's no question that Ackquille Pollard is a driving force behind the GS9 gang and an organizing figure within this particular conspiracy. The prosecutor goes on to talk about all kinds of criminal activity involving Bobby - weapons, drugs, even shootings in broad daylight.

MADDEN: Bobby is facing a long list of charges, including weapons possession, reckless endangerment, conspiracy to sell narcotics and even conspiracy to commit murder.

BOBBY SHMURDA: It's bullshit. That's why they always put conspiracy on you. So if they can't get you on one, they can get you on one charge. And when they get you on one, they going to give you the max. That's what they do. So they put a whole bunch of bullshit charges so you could just blow to at least one. And they give you the max.

CARMICHAEL: Yeah. Bobby, he watched two of his closest friends, A-Rod and Rasha, go to trial and get convicted for the murder of Bryan Antoine and other shootings. Both were handed what could amount to life sentences.

BOBBY SHMURDA: A-Rod got 53. Rasha got 98. How the law works is when you go to trial and stuff like that, they usually paint pictures. They don't go by they law. Motherfucker talking about some 30 years. I said, 30 years? What the fuck. You talking about 30 years for what? These people crazy.


CARMICHAEL: I'm Rodney Carmichael.

MADDEN: I'm Sidney Madden.


MADDEN: Where we trace the collision of rhyme and punishment in America.

CARMICHAEL: In our final episode of the Bobby trilogy, it's Bobby Shmurda versus the law.

MADDEN: We talked to the prosecution, the defense and the man caught in the middle.

CARMICHAEL: Legally, Bobby has two choices on his hands. He could face a jury trial and risk getting decades in prison or plead guilty for a fraction of the time.

MADDEN: But really, the only choice in Bobby's mind is go for crew or go for self.


CARMICHAEL: When Bobby got indicted after that Quad Studios raid, his first lawyer on the case was this guy.

HOWARD GREENBERG: Poor excuse for a criminal defense attorney Howard Greenberg at your service.

CARMICHAEL: Yeah. Howard's earned himself a lot of nicknames over the years, like New York's Last Chance Lawyer. But he's probably best known as a real-life Better Call Saul.

MADDEN: Before Bobby was implicated in this conspiracy case, Howard had previously helped him beat some weapons charges.

GREENBERG: Well, he was my favorite old Jewish man because, you understand, I had never met him. And I'd never heard of him. So when I got a call that someone wanted me to represent Bobby Shmurda, I said, look at this. I'm finally going to get to represent an old Jewish guy in court, Bobby Shmurda. And if that's not a Yiddish last name (laughter), I don't know what the hell is.

MADDEN: So as you can probably tell, Howard is pretty eccentric. He's got dyed, jet-black hair and a baggy suit. His second-floor walk-up office near Copperhill, Brooklyn, is adorned with just as many articles about himself as framed, full-sized, gangster movie posters.

CARMICHAEL: Yeah. Despite Howard and Bobby being different in almost every way you could imagine, he was actually in Bobby's shoes once upon a time.


CARMICHAEL: He'd seen conspiracy cases before from the inside. In the 1980s, a young Howard Greenberg was working as a copywriter for an ad agency...

GREENBERG: When I met the gal who turned out to be the daughter of a well-known Mafioso.

CARMICHAEL: Now, he claims he had no idea about this till after they were married.

MADDEN: Then, in the spring of 1984, their home got raided by the feds.

GREENBERG: They arrested and took into custody, destroyed my then-family by marriage.

CARMICHAEL: Yeah, his wife's family had been implicated in the infamous pizza connection case. The Sicilian Mafia had been smuggling heroin and cocaine into the U.S. and selling it through pizzerias across the country.

GREENBERG: And by the time it was tried, it was the longest federal trial in the history of the United States of America.

CARMICHAEL: Two dozen people were tried under the RICO Act. RICO was created way back in 1970 in order to take down organized crime rings that had plagued big cities like New York and Chicago for decades. You know, think mob families like the Gambinos, organizations with hierarchy.

MADDEN: Yeah. And remember, earlier this season, we told you how RICO was used to take down DJ Drama in that mixtape raid in '07. Conspiracy laws like RICO allow prosecutors to hold anyone in the entire enterprise responsible for the worst thing someone in the circle has done.

GREENBERG: Conspiracy is an agreement to do something illegal with one or more people. And then someone who is a part of the agreement just has to commit a single act in furtherance of the conspiracy.

CARMICHAEL: Twenty pizza connection conspirators were convicted due to a wiretap, a paper trail and witness evidence.

MADDEN: Howard's father-in-law and his wife's uncle both were ultimately convicted.

CARMICHAEL: Yeah, and that springtime raid - man, it changed Howard's life for good.

GREENBERG: So anyway, that's how I got into this business. That day, with the FBI locking up people I loved and dogs crawling all over our home in Stone Ridge, N.Y. - that day, I decided to become a criminal defense attorney.

MADDEN: Now, even though GS9 was not being prosecuted under federal RICO law like Howard's former family, all conspiracy laws have similarities. So Howard felt like he knew how to defend Bobby successfully. He decided Bobby needed to distance himself from GS9 in order to make claims of conspiracy as flimsy as possible.

GREENBERG: You're not your brother's keeper, you know? And my theory about defending him - this kid was rich. And he was busy. He didn't have the time to get into this bullshit with the people that were hanging on him and around him. And I still believe that until today.

CARMICHAEL: But see, here's the thing about Howard's theory. It doesn't take into account the code of the streets that Bobby came from. For Bobby, you are your brother's keeper. And GS9 - to him, it was a brotherhood. But Bobby's celebrity would put even more eyes on his crew.

Well, how much do you think that Bobby being this sudden success story...

GREENBERG: Everything to do with his arrest. So he's 19. He just signed on for a million - whatever it is - with a record company. The scumbags, who are hangers-on, in and around him did bad things that were all documented. And he was an easy target for law enforcement.

MADDEN: But Howard never got to use his rich and busy defense in trial. According to Howard, he was fired out of nowhere by Epic Records, who Bobby says was footing the bill.

GREENBERG: Well, I was getting the case ready for trial when I was unceremoniously relieved of my duties by folks who think they know better.

MADDEN: This was also around the time that the Office of the Special Narcotics Prosecutor picked up Bobby's case, and the case was transferred from the Brooklyn court system into Manhattan. And the special narcotics prosecutor was going to make Bobby's case even more of an uphill battle.

CARMICHAEL: Yeah, and this is a super unique office, special narcotics prosecutor. None like it anywhere else in the country. It has really broad powers, too. See, unlike a district attorney's office, it has citywide jurisdiction and takes cases from all five boroughs, especially drug trafficking rings that distribute all over the city.

BRIDGET BRENNAN: Our office's mission is to focus on the critical issues that are facing the city and their relationship to drugs.

MADDEN: That's Bridget Brennan. She's been the head of the special narcotics office for 22 years, and it's expanded under her watch. A decade or two ago, GS9's case probably wouldn't have ended up in her office. But by 2014, crime was on the decline in New York. Arrests for murder and drug felonies had gone down. So even though the amount of drugs GS9 was pushing seemed small, she says GS9's violence is what stood out.

BRENNAN: This organization was involved in a spate of violent crime here in the city. Neighborhoods were terrorized, and it initiated with complaints about dealing drugs.

MADDEN: Notice what she calls GS9 - an organization. That's going to be important later.

CARMICHAEL: Yeah, and with crime as low as it was, Bridget had the bandwidth to take down GS9. Plus, conspiracy law gives prosecutors lots of flexibility to build a case, especially one who's already as powerful as Bridget Brennan.

MADDEN: To prove a conspiracy charge, you have to show that defendants made an agreement to break the law. And Bridget's office brought in evidence like social media posts and phone conversations in order to prove that.

BRENNAN: And what's important about a conspiracy charge, certainly to a jury or to a judge, is that it allows you to put people in the context so that it's not merely possessing a weapon without any kind of context of how or why. And so it allows them more information and a better insight. And so it's an important tool.

MADDEN: Information, insight - she's basically saying that conspiracy law gives her the ability to put together a narrative about the group and tell a story in court that can easily persuade a jury. When it came to Bobby's involvement, the prosecution's story was this - police caught Bobby with guns, artillery for GS9's ongoing gang war. And even though Bobby may not have been part of the shootings of Bryan Antoine or the female bystander, according to Bridget, he was still complicit in those shootings.

BRENNAN: I think the way we characterized him was a driving force.

CARMICHAEL: Now, Bridget - she says she didn't take Bobby's celebrity into account. But she points out that the crimes didn't stop when Bobby got famous either.

BRENNAN: As the group's musical efforts seemed to get more traction and more notoriety, the violence actually escalated and became more reckless and bolder.

CARMICHAEL: Police say five shootings happened after "Hot Boy" went viral, and one of them even happened in Miami while Bobby was there for a scheduled performance. And according to Bridget, Bobby was making a lot of money off music and flipping that money to fund the beefs.

MADDEN: So instead of music lifting Bobby out of trouble like Sha had hoped, Bridget argues it dragged him lower. It actually fueled more violence. And as part of that narrative, Bridget's office used conspiracy law to add conspiracy to murder on top of Bobby's list of charges.

CARMICHAEL: His name even appeared at the top of the initial NYPD press release. His bail was set way higher than most of his friends' at $2 million. If the prosecution was treating GS9 like a modern day mafia, Bobby was most definitely being painted as the mob boss, the kingpin.


MADDEN: And the sentences that were being passed down were as harsh as if they actually were mob family. Remember Rasha and A-Rod? They're going to spend most, if not all, of their lives in prison.

CARMICHAEL: Now, we asked Bridget if prosecutors like her ever take into account the overarching circumstances that contribute to living this type of life that make it possible for Bobby to be selling crack since the fifth grade, or if they only see long prison sentences for young Black men as the solution to the problem.

BRENNAN: Well, of course, we think about what can be bigger, broader solutions. And I think you also have to keep in mind that this neighborhood, all the neighborhoods in our city, are full of people who struggle. And this kind of behavior is very rare behavior. I mean, people - a lot of people have it tough. And they manage to live their lives peacefully, lawfully. And they are victimized by gang violence. So the real challenge is, how do you balance all that out?

MADDEN: She says Rasha and A-Rod were old enough to know better and pointed out that they never showed any remorse in the courtroom.

CARMICHAEL: Yeah, I mean, basically what she's saying is sometimes you've got to take out the bad apples so they don't spoil the Big Apple.

BRENNAN: And obviously, earlier interventions are critical. But by the time the case or something like this is something we become involved in, it's often long past those times.

CARMICHAEL: But see, this rationale - it totally glosses over the inequalities that plague a neighborhood like Bobby's, the things that distinguish the struggles of East Flatbush from the Upper East Side. Nevertheless, Bobby's day in court was just months away.


MADDEN: It's a dreary day in December 2019.


MADDEN: We're in the car with attorney Kenneth Montgomery. He's the lawyer Bobby hired after dropping Howard Greenberg. Jazz plays on the radio as we drive down Eastern Parkway and debrief about what we saw while shadowing Kenneth in court earlier that day.

We're leaving court.

KENNETH MONTGOMERY: We're leaving 100 Centre St., Manhattan Supreme, and heading to my office in Brooklyn.

MADDEN: Can you tell us about the feeling of the courtroom?

MONTGOMERY: For me personally, it's a sign of oppression. Look who are the people who are going before the judge. Most of them are people - men, particularly - of color, people in the throes of poverty. Most of the judges, most of the prosecutors, are white.

MADDEN: I know you deal with it - you're, like, in and out of courtrooms all the time and might be, like, desensitized to the feeling...

MONTGOMERY: Not desensitized because when you desensitize, you shouldn't do this work.

MADDEN: We arrive at his office in Crown Heights, where his awning reads Criminal Defense, Civil Rights, Personal Injury. And under that, the glass in the front window has been wrapped with a blown-up photo of Black boys in the 1980s, an image shot by legendary street photographer Jamel Shabazz, a close friend of Kenneth's. You get the sense that this isn't just an expression of his work. It's who Kenneth is.

CARMICHAEL: Now, when Kenneth took on Bobby's case, he understood it as pretty much open and shut.

MONTGOMERY: It wasn't anything abnormal about the case. It was a special narcotics investigation. I've represented tons of those cases before, state drug conspiracy cases with some violence. The only thing that made that case unique was that two of the young men had recording deals.

CARMICHAEL: Yeah, so their relationship was pretty much like this - Kenneth wanted Bobby to face the facts of the case, and Bobby - he wanted to do anything but. But Kenneth also understood where Bobby was coming from.

MONTGOMERY: I did feel a certain sense of responsibility in someone who could have been my son, tried to get to him.

MADDEN: We wanted to spend some time with Kenneth to understand why this case was so important to him. But in the process, we also discovered how similar Kenneth and Bobby really are. Just like Bobby, Kenneth came up in Brooklyn - Brownsville, to be exact.

CARMICHAEL: Yeah, and as a youngster, man, Kenneth was kicking up much dust.

MONTGOMERY: Running around acting crazy with my friends, robbing people on trains, fighting other groups of kids, running into stores, robbing stores, boosting - and danger was always a second away.

CARMICHAEL: That was the code of survival that he was learning to live by. Take the time in high school when he and his friends, all from Brooklyn, started hanging out with a kid from Harlem. Now, this guy's Harlem homies - they were not feeling that.

MONTGOMERY: They beat him up, put him in the hospital in a coma. We find out. Everybody from Harlem we see, we beat them up.

MADDEN: And one of those fights got vicious.

MONTGOMERY: He just happened to punch me in the chin. It was wintertime. He had a razor blade in his fist. When - if anybody who's been in a fight in the winter, you don't really feel much. So because it was a razor blade, it was a clean cut, I didn't even know I was - I just kept fighting. I didn't know I was cut to that degree.

I remember all of the old guys that I looked up to who was fond of me had told me, like, I had to get somebody back for that. So it was a period after I got cut in the face where I definitely assaulted quite a few people with razor blades on the trains - A train, four or five line, definitely, as a form of getting back.


MONTGOMERY: You know, there's something about not wanting to be a victim and trying to control your scenario, not becoming a victim. And when you get victimized, you don't ever want that. You hate that feeling. You don't want to be victimized again.

CARMICHAEL: Yeah, but protecting yourself - that was only one part of it.

MADDEN: It was also about projecting - projecting an image in an environment where image is everything.

MONTGOMERY: And when you live in a concentrated neighborhood like that, where you're always on stage, that's very important because that affects how you're accepted by your peers. I mean, that affects how people treat you, how they look at you. And that was peer pressure at its finest.

MADDEN: Sounds a lot like Bobby, right?

CARMICHAEL: But in Kenneth's case, he got a chance to outgrow it.

MONTGOMERY: I think Bobby - and the difference with me and him was that I think he embraced it. I knew all that shit would get you in trouble at some point.

CARMICHAEL: Kenneth eventually went to college and then to law school. And having that opportunity - it really broadened his options, but it also expanded the way he saw himself.

MONTGOMERY: I had internalized being a lawyer with being smart. And I had internalized that America didn't think we were smart. So for me, a lawyer was to be smart and to be dangerous to the system.

CARMICHAEL: Smart and dangerous.

MADDEN: Mmm hmm.

CARMICHAEL: Now, after he passed the bar, Kenneth didn't go straight into the type of defense work that he's become known for. He started his career - check this - as a New York City prosecutor.

MONTGOMERY: A gang prosecutor, in fact. I was in a unit that - one of the first prosecutor's offices in the city that started cultivating gang cases.

MADDEN: This was in 1997, around the same time Bridget Brennan was moving up through the ranks of the special narcotics office.

CARMICHAEL: And being a prosecutor - it might seem a little out of character for Kenneth, right? But see, he knew that it would make him a better defense attorney in the long run.

MONTGOMERY: And that's the only reason I became a prosecutor.

CARMICHAEL: Just to learn from that other side.

MONTGOMERY: To get the information, to be the spook by the door.

CARMICHAEL: OK, yeah, perfect analogy.

MONTGOMERY: That's the perfect analogy.


MONTGOMERY: Personally, when I look back at it, it gave me a really close-up view to how insanely unfair the system is. You come to work one day, you approach the bench to speak to the judge and the judge tells you no defendants at the bench. You go to brief a case and the prosecutor, supervisor, white supervisor - he sees the kid who's grown up in East New York with an East New York Brownsville address, and he makes racist assumptions about that kid and what his crime or his accusation is or what his bail should be. It's not a mistake that we have 2.5 million people in jail and the majority of them look like that. It's - this is not a mistake. This is what - you want apples, you go to an apple orchard. You want defendants, you go to Black and Hispanic neighborhoods.

MADDEN: And when Kenneth took on Bobby's case, he saw it as an extension of all those problems.

CARMICHAEL: And it was clear to him why the prosecution was using conspiracy charges to bring down Bobby and GS9 all at once. But he definitely didn't believe in comparing GS9 to the mafia.

MONTGOMERY: A group of kids growing up in an oppressed neighborhood with no organization, no structure, no pattern, no suppliers, making no money - that's not an enterprise. A neighborhood is not an enterprise. It's not a gang.

CARMICHAEL: Kenneth definitely thought the charges were overblown.

MONTGOMERY: The conspiracy to commit murder was weak because they cannot point to anything that I thought they can say Ackquille Pollard was instrumental in someone being shot and killed. They were doing that based on the association.

CARMICHAEL: In fact, Kenneth says, just look at the wiretapped phone calls.

MONTGOMERY: There's nothing in these conversations where you can say Bobby Shmurda was some sort of leader ordering and directing these people to do anything.

MADDEN: Remember, prosecuting a case of this kind means creating a narrative - that GS9 was a gang and that Bobby was, quote, "the driving force." And who would that narrative be most effective on? A jury made up of people outside his community.

MONTGOMERY: You take a bunch of kids, a bunch of people from Brooklyn, and all of a sudden now they're being prosecuted in Manhattan.

CARMICHAEL: Why is that distinction important? Why is taking a Brooklyn cat to Manhattan different?

MONTGOMERY: It changes the nature of the prosecution. You take a case out of Brooklyn and you put a young kid in a Manhattan jury, which traditionally know nothing about the issues that happened in Brooklyn, and now they're judging. That's not a judge of your peers.

CARMICHAEL: So you see, it really didn't matter how wrong Kenneth Montgomery or Howard Greenberg performed, though the prosecution was about Bobby and GS9, how many holes they could poke in those arguments Bridget Brennan made. The fact was Bobby would face a tough crowd in court. And on top of that, he could be made responsible for his friend's actions. These tactics - they've become more and more common among prosecutors in recent years, especially against crews like GS9.

MADDEN: And you know what? GS9's prosecution isn't even the most blatant example of this. Prosecutors are still using conspiracy law as justification to round up groups of Black men all the time. Not long after the GS9 raid, there was a federal RICO case that happened in 2016 known as the Bronx 120.


UNIDENTIFIED REPORTER: Sources say hundreds of gang members are being arrested this morning here across the Bronx. It's happening now as we speak. We're in front of the 43rd Precinct station house...

CARMICHAEL: The massive raid, co-organized by the NYPD, DEA and Homeland Security, is considered one of the biggest "gang takedowns," quote-unquote, in U.S. history.

MADDEN: That's 120 people rounded up in the middle of the night. An army of police officers in tactical gear swept through the Bronx neighborhood of Eastchester.


CARMICHAEL: The district attorney at the time said the men were charged with racketeering, narcotics and illegal firearm charges. But that's not all.

BABE HOWELL: There were eight homicides associated with that sweep. That's 112 who didn't do the homicides all getting painted with a - you're in a RICO conspiracy that includes murder.

CARMICHAEL: That's Babe Howell. She's a professor of criminal law at City University of New York and a seasoned defense attorney. Babe's been following the policing of street crews for years, and she draws a huge distinction between crews and gangs. The way she puts it, crews don't have hierarchies of rules. There's no beating in and beating out. But the NYPD and prosecutors - they see it differently. They still call them gangs, and they prosecute crews as organized crime outfits.

HOWELL: Even actual proof of membership is not needed. The colors you wear, the bodega you go to, your cousin, your yearbook photos - all of that can be used as evidence that someone's a gang associate or gang member. Conspiracy laws make a conspiracy incredibly easy to prosecute, nearly impossible to defend, and they carry very, very harsh penalties.

MADDEN: According to Babe's research, when all was said and done, most of them were only guilty of misdemeanors, like marijuana sales. But they ended up pleading to felony charges because of RICO, and the vast majority of those convicted were under 30 years old. So whether they were convicted or not, whether they were found to be in a gang or not, that was 120 young men who were put into contact with the system and strapped with felony charges.

CARMICHAEL: In fact, a recent study showed 86% of federal RICO prosecutions involve people of color - 86%. Now, people who defend conspiracy laws typically argue that they might be a deterrent, a tactic to persuade young folks not to join gangs. But here's what's wrong with that logic - putting people behind bars often has the opposite effect.

HOWELL: Gang membership is a transitional phase. It's - people tend to join in adolescence. They quit a year or two later. They get a job. They have a child. They find a girlfriend. They move out and move on. It's very unusual for a gang member to stay a gang member over years or decades. But if we arrest, prosecute, and imprison at this critical moment in life, then the gang identity becomes the most important part of their life, and they're usually trapped by the criminal justice system, by the felony records, into identifying even more strongly with the gangs.

MADDEN: Even though Bobby's crew was smaller than the Bronx 120, they were facing a similar kind of case. And Kenneth knew that. In fact, he had defended a member of the Bronx 120. He knew the risks of taking Bobby's case to trial. He took a hard look at the evidence and was faced with a difficult reality.

MONTGOMERY: I thought a kid that age with that much at stake with evidence that was - I'd say it was probably overwhelming for the type of case that it was - it was - a trial was nonsense.

CARMICHAEL: Yeah, he actually thought Bobby should plead guilty to avoid trial. I mean, that is the way it goes for 94% of criminal defendants. Prosecutors offer them a plea deal, and they take it.

So what's the first piece of advice that you were giving to Bobby and his family once you've had a chance to, you know...

MONTGOMERY: Look at the evidence?


MONTGOMERY: I told them that I think we should see what's the lowest number we can get and get him in and out of this thing.

BOBBY SHMURDA: I'm like, what you mean, the lowest time? So I said, you're supposed to be going to the district attorney, something, you know what I mean? Not district attorney, the attorney general. You're supposed to be doing a whole bunch of other shit.

MADDEN: Tensions got so bad that there wasn't much more Kenneth could do. So Bobby fired him. He was determined to have his day in court.


CARMICHAEL: By the end of 2015, Bobby had been locked up and awaiting trial for almost a year. He'd spent his 21st birthday in jail. His career was on hold. And all these crucial markers of his adulthood, they were basically frozen in time. That summer, Bobby hired his third lawyer, Alex Spiro.

ALEX SPIRO: I saw a scared kid, and I wanted to help him.

CARMICHAEL: Now, Alex is a well-known Manhattan attorney from a top-tier law firm who's also represented the likes of Jay-Z. He's currently the lawyer on staff at Roc Nation's criminal justice arm, Team Roc. Now, according to court documents we reviewed, Alex had tried everything he could to help Bobby's case by filing motions to dismiss some evidence and throw out some of the charges. But none of that worked. The odds against Bobby had just stacked higher and higher.

MADDEN: And Bobby was never able to raise that $2 million bail. So at this point, he'd been stuck behind bars for nearly two years.

SPIRO: Having an incarcerated defendant disconnects them from society. It makes it harder for them to defend themselves, harder to work with their lawyer, harder to review discovery and evidence, harder to procure witnesses on their behalf.

MADDEN: On a Friday in September 2016, the prosecution finally told the judge that they were ready to begin trial in the case of Bobby and his three GS9 co-defendants - Rowdy Rebel, Montana Flea and Cueno. Jury selection was scheduled to begin in three days.

SPIRO: Trials are very unpredictable. Let's say the chances of losing is 10%, but 10% is life in jail. That 10% has to be weighed awfully seriously.

MADDEN: So the prosecution gave Bobby and his friends an ultimatum - take a plea deal, or go to trial.

CARMICHAEL: But there was a catch. See, the type of deal that they were offering - it's called a global plea deal. And if one co-defendant declines the offer, none of them get it. Bobby is facing more than 50 years if convicted, and even though Alex believes the case against Bobby is overstated, he still saw it as an uphill battle.

SPIRO: Because they had had him in jail - right? - and they had already taken two years from him, they were in a better bargaining position than he was.

CARMICHAEL: So according to court transcripts, here's what went down next.


CARMICHAEL: One by one the judge asked the defendants if they accept the prosecution's terms, if they would take the plea deal. And again, it's Bobby, Rowdy Rebel, Montana Flea and Cueno. Rowdy Rebel is offered seven years. He agrees to plead guilty. Montana Flea is offered seven years. He agrees to plead guilty. When the judge gets to Bobby, he offers him seven years. And this is what Bobby tells the judge - "it's my understanding that my co-defendant is not interested."

MADDEN: The judge says, "I'll have to speak with him separately. My question to you is whether you're interested."

CARMICHAEL: And Bobby thinks for a moment, and then he decides to take the deal. "Yes, Your Honor," he says.

MADDEN: Cueno's up next. He's the co-defendant Bobby was referring to. But unlike the others, Cueno has been charged with committing several non-fatal shootings, so he's being offered the most time - 15 years. Check this - Cueno decides not to take the deal. The judge says he has to take it or everybody's going to trial. Alex remembers this moment as being tense.

SPIRO: For anybody who's in that kind of a situation, how could it not be scary? How could it not be overwhelming? How could it not be frustrating?

CARMICHAEL: The lawyers approach the bench to hash out this deal. And in the end, Cueno gets severed from the deal, so Bobby, Rowdy and Montana are allowed to take the plea without him.

MADDEN: And Cueno - he ends up going to trial and being found guilty, and he's sentenced to a minimum of 117 years for 23 counts, including attempted murder.

CARMICHAEL: Now, that's about eight times longer than the deal he was initially offered.

MADDEN: As for Bobby, he was originally charged with eight counts, including conspiracy to murder and reckless endangerment.

CARMICHAEL: But in the end, he only had to plead guilty to two crimes - one count of weapons possession and a related conspiracy charge.

MADDEN: Yeah, the prosecution dropped the other six counts, including the most explosive one, conspiracy to murder. Howard and Kenneth both told us that evidence for that charge was weak anyway.

CARMICHAEL: Now, Bridget was pretty reluctant to talk about anything Bobby was charged with but didn't plead guilty to. So we asked her, did you have the evidence to convict Bobby of conspiracy to murder if it had gone to trial? Or was it just a negotiation tactic to secure his conviction?

BRENNAN: What difference does it make in the end, right? I mean, he pled guilty to charges that he agreed he was guilty. We agree he's guilty. I'm not going to talk about the murder conspiracy because we didn't prove that charge beyond a reasonable doubt. We wouldn't have brought it had we not thought we could prove it beyond a reasonable doubt. But I hardly view his plea as anything but appropriate. So I'm not going to now talk about how they might be guilty of other crimes that they did not plead guilty to. It wouldn't be fair, and it wouldn't be right.

CARMICHAEL: Critics of plea deals see it differently. To them, what isn't fair is how prosecutors throw everything but the kitchen sink at defendants in order to get them to agree to a plea deal with little justification, especially when 94% of state-prosecuted cases end in a plea deal.

MADDEN: So what's clear is this - Bridget Brennan withdrew the conspiracy to murder charge in Bobby's case, but it's still helped her get a guilty plea out of Bobby in the end. Bobby says he only took this deal to help Rowdy and Montana Flea avoid trial. Otherwise, he says he would have fought for less time or gone to trial himself.

CARMICHAEL: Yeah, that's the reason why Bobby is still seen as a hero and even a martyr to a lot of folks. It's why so many in hip-hop are really rooting for him when he gets out.

SPIRO: So the irony, of course, is that where this conversation started is that these kids, like I said, stuck together like brothers. And at the end they were told, if you don't stick together now, your brother may get more time.

CARMICHAEL: One month later, Bobby's back in court. And this time, it's for his sentencing hearing. Now, at this point, the plea deal is already locked in, so this should just be a formality. But then something goes left. And this right here - this is the climactic part of Bobby's sentencing hearing that doesn't get talked about enough. It's here where Bobby tries to renege on his plea deal in court.

MADDEN: On this day, Bobby's alone. None of this GS9 co-d's are with him. According to court transcripts, Bobby tells the judge in the middle of the hearing, "I want my plea back. I was forced to take this plea. I don't want it. Take it back," he says again. "I don't want the plea."

CARMICHAEL: And that's when his lawyer, Alex, jumps in, trying to smooth over the situation. Alex says, "my client is clearly frustrated." He explains that Bobby is concerned about, quote, "the way conspiracy laws work to make him responsible for his friend's actions."

MADDEN: "Leave me alone," Bobby tells Alex. "I withdraw my plea, and I'm firing you."


CARMICHAEL: Now, all of these details come from court documents. We don't know what Bobby looked like or how he sounded in the moment. But based on the transcripts, it definitely seems like he's frustrated and unwilling to accept this outcome. Prosecutors have used these conspiracy laws to rope him into pleading guilty, and to him, it obviously feels unfair.

MADDEN: Yeah. I mean, think about where he's at. He's on his third lawyer. He's not satisfied with the deal he's getting, but he's also seen his friends go to trial and get some brutal sentences. Bobby sees this moment as his last chance to challenge a process that doesn't make sense to him. We asked him about that when we interviewed him.

BOBBY SHMURDA: I wasn't going to take the plea because I didn't feel like - the evidence wasn't good enough for me to be taking a plea.

CARMICHAEL: We also asked his lawyer Alex about the moment Bobby tried to fire him.

SPIRO: All I can say is on something that has this much on the line and this much emotional charge with somebody young who the system, in many ways, failed, I would expect that a person would have second thoughts about it on a day by day basis - right? - I mean, because you never know what would have happened down road No. 2.

CARMICHAEL: The judge tells Bobby it's too late and that his outburst is also not a formal way to submit that kind of request. I was satisfied when I accepted your plea that your plea was voluntary, the judge tells him. Then he sentences Bobby to a maximum of seven years in prison.

MONTGOMERY: And by the way, guys - hold on.


MONTGOMERY: These guys in the back are from NPR.


MADDEN: When we catch up with Kenneth Montgomery again, it's on the last day of the fall 2019 semester of his class at Brooklyn College called Blacks and the law. We're sitting in the back of the classroom, observing him teach.

CARMICHAEL: And Kenneth hasn't spoken to Bobby in five years, but, man, it's clear that he's still thinking of them, especially as he addresses his students.

MONTGOMERY: Because I also represent - I do a lot of federal work. I do capital murder. I get the calls when the young rappers who supposedly gang get jammed in Brooklyn. And it seems like everybody getting signed from Brooklyn has affiliation to gang, you know, whether it's Pop Smoke or - it's true, right?


MONTGOMERY: Bobby Shmurda - who else is involved...

MADDEN: He's basically recapping the entire semester, pointing out how these cases involving rappers are part of a bigger history of systemic injustice.

MONTGOMERY: And that's more or less what we talked about a couple of classes ago when I said that there was this gentlemen's agreement by both sides, the most powerful political parties in this country, that this society would be run and inspired by a racial caste system. And one of the ways that it's done - it is the legal system.

MADDEN: At the end of class, Kenneth passes out final papers.

MONTGOMERY: Denzel, Gabriella - and that's it, guys. I really enjoyed it.



MADDEN: Some students stick around after class to thank Kenneth. But after that, we sit in empty classroom with him to chop it up. We asked him what he thinks Bobby's story says about the link between hip-hop and mass incarceration and what's missing from the way we talk about Black and brown men and their entanglement with these systems. He tells us about an image that went viral right around the time he was repping Bobby in court.

MONTGOMERY: You know, it's this stupid meme that goes around of me, him and a court officer boy of mine. I don't know if you've seen it.

MADDEN: Yeah, yeah. We've seen it.

CARMICHAEL: Yeah, man. And in this meme, Bobby's in a prison-issued gray sweatsuit, and his hands are cuffed behind him. And Kenneth is standing beside him in a sharp gray suit. He's wearing a nice watch. His arms are crossed, and he's looking down like he's contemplating his next move. But behind them, there's a law enforcement officer, full uniform - you know, like a bailiff - standing there super-straight and at full attention. All three men are Black, and The caption says, three men in three different positions - in America, your color doesn't define your future. Your choices do.

MONTGOMERY: And it looked like it was probably drafted by some young Proud Boy or right-wing guy who wants to inject in the social meme factoidal world we live in now. But everybody don't have autonomous choices. Everybody got choices. Everybody don't have free, autonomous choices. Your free - your ability to have a free and autonomous choice is impacted by the community you come from. I think Bobby was doing in the street what he was bred to do.

White America, corporate America saw the commodity in it. So it's like America commodified Black pain, Black death. And it did it really, really well. It did it so efficiently and seamless that we don't even question it anymore.

CARMICHAEL: But, see; then on the flipside, like, you also got to acknowledge that for a lot of cats, hip-hop is a way out.

MONTGOMERY: Yeah, but listen. Let's do the numbers on that. What's the numbers on that? Like, yo; the numbers is - like, yo, you're going to need fairy dust if you think that - you know, here's the problem. With media, it gives the impression that the odds are greater than what they actually are. White kids are getting the same music and information. Why is it that white kids want to be entertainers?

CARMICHAEL: They have more options.

MONTGOMERY: Entertainers have now become synonymous with Blackness.


MONTGOMERY: We have to have a serious reflection process. Our solutions have to be appropriate - not only to the problem, but they have to have room to breathe to create an opportunity and a roadmap for a future generation of young people.

MADDEN: Young people like Bobby, who Kenneth still has hope for.

MONTGOMERY: His mother approached me one day when she saw me outside of court in Manhattan and she said she's sorry, that, you know, she should have listened. I said, you don't owe me an apology. I told her the best thing that I think could happen is that this kid is going to come home still a young man and hopefully with some maturity and a different perspective, and he gets to control his narrative a little bit better. And I wish him well, you know?

CARMICHAEL: Bobby's been serving out his prison sentence for about six years now up at Clinton Correctional Facility in Dannemora, N.Y. Now, this prison - man, it's held inmates since 1845. And Bobby's far from the only rapper to be imprisoned there. Rappers ranging from Shyne to Ol' Dirty Bastard to Maino and even Tupac, who immortalized Clinton Correctional when he namedropped the prison in his '96 track "Picture Me Rollin'" after doing a bid there.


TUPAC: (Rapping) No. 1 on my list, Clinton Correctional Facility. All you bitch ass COs, can you niggas see me from there, ballin' on y'all punk asses?

MADDEN: In 2018, we made the five-hour drive up to Clinton Correctional to visit Bobby. And the first thing you once you get up there is how much the prison seems like the center of gravity for the whole town. It's just scattered houses, a couple of car dealerships, and then these 60-foot-high gray walls shoot straight up to the sky.


MADDEN: It takes us about 20 minutes to get through security. After that, the CO sets us up in a small interview room with barred windows, a table, two chairs and a rotating fan.

CARMICHAEL: Then, after a few minutes, Bobby comes in through a separate doorway with two officers who stay in the room during the whole conversation.





MADDEN: What's up? Good morning.


MADDEN: I'm Sidney. Nice to meet you. We talked on the phone.

CARMICHAEL: I'm Rodney, man. Good to meet you. You been waiting on us long?

MADDEN: When he first walked in the room, the first thing I noticed was how much more grown he looked, much more filled out than that little kid jumping around in the "Hot Boy" video in 2014. And his smile was really bright.

CARMICHAEL: Yeah, but behind that smile, man, his eyes looked a little sad to me, kind of distant.

MADDEN: Especially when we asked Bobby about his case.

How do you feel about them kind of, like, painting you as the ringleader in the whole indictment?

BOBBY SHMURDA: They only did that because of the Bobby Shmurda shit and that I was CEO of the label. It was painted as, I had the money, I'm the gang leader. And the people I grew up with - they murderers and stuff like that, all this crazy stuff. And that's how they painted the picture, and people just go along with it, you know what I'm saying? Because they have a badge or something, so now they look that their word is golden.

MADDEN: What's something people don't know about you that you feel they should?

BOBBY SHMURDA: I'm not a criminal (laughter).

MADDEN: Elaborate on that.

BOBBY SHMURDA: Oh, I'm not a criminal. I always looked at myself - like, even people in here, they call me, like - they say convicts. We felons. But I don't look at myself as a convict or a felon. I look at myself as a hostage right now.

CARMICHAEL: Bobby says he read through his own case file for the first time in jail while he was in protective custody.

BOBBY SHMURDA: I knew it was bullshit. The bail, everything - I knew it was bullshit.

MADDEN: Do you feel like - have you learned more about, like, gun charges and conspiracy laws now on the other side of it?

BOBBY SHMURDA: Yeah. I know I got to get security when I go home this time. I know that (laughter). So I got like - I learned about the gun law more because that been my problem. So I learned that even as a felon, I still can't have a gun, but I can have security. So I told my bros who don't got felonies and stuff, go get your license and stuff like that. You know what I'm saying? I tell a lot of people, rappers, these days all that, too. You know what I'm saying? Because nobody wants police as security.

CARMICHAEL: Now, this is the closest Bobby ever gets in our interview to acknowledging any wrongdoing associated with his conviction, to basically admitting that he had guns for security, and security will probably still be a necessity for him when he gets out and jumps back into the music game.

MADDEN: Yeah, and he's ready to get back. He's still keeping his ear to the streets.

Do you stay up-to-date on what's happening in hip-hop right now?

BOBBY SHMURDA: Yeah because all my bros out there - they running around with a lot of new rappers.

MADDEN: Nice. And how do you get it in here? How do you get to listen to...

BOBBY SHMURDA: It's like 18th century in here. We've got cassette players. This shit's crazy. I ain't never seen a cassette player in my life since I got here. I'm like, what the fuck? You've got cassette players. That shit is crazy, like, the 1800s (laughter).


In the years since Bobby went away, the sound of New York has definitely changed. U.K. and Chicago Drill has migrated to New York and been mixed with the West Indian flavor of the Brooklyn streets Bobby grew up on.


MADDEN: Now, Brooklyn drill has taken over. And artists like the late Pop Smoke or even GS9-affiliated acts like Fivio Foreign or Fetty Luciano, they're making waves.


POP SMOKE: (Rapping) She like the way that I woo.

MADDEN: And a lot of the seeds of this movement trace back to that viral whirlwind that Bobby and Rowdy created back in 2014. That's another reason hip-hop fans can't wait for Bobby to come home, to see and hear what he'll do with the evolution of this sound.

SHA MONEY XL: It's going to be that shit. That nigga going to spit, rip - he going to go. He don't lose that. That shit is him. It's in him - DNA.

CARMICHAEL: Even after how everything went down, Bobby's former A&R Sha Money XL still believes Bobby's future is bright. And unlike the last big-name Brooklyn rapper, Tekashi69, who came home from prison regarded as a snitch for testifying against his crew on the stand, Bobby's set to be celebrated as a hometown hero for sticking to the G code.

SHA MONEY XL: This next shot he got, make the wisest decision. I want him to grow, do his thing, make all the money he didn't make plus more - become a Jay-Z, become that guy that will become an example. You know what I'm saying? Change it. Change the paradigm, man. He could do it. All eyes is on him like Tupac, man. You know what I'm saying? Don't do the wrong thing, man. Do the right thing. Be - stay righteous.

MAINO: He's going to come home even more respected, even more popular.

MADDEN: Yeah. Maino's got hope for Bobby, too.

MAINO: Man, all Bobby got to do now is just take advantage of the system. You know, he's going to come home, he's going to come home hot. So take advantage of that. Get to the money. Get to the bag. Get in the studio. You want to wake up and see cars in your driveway. You want to - man, come on.

MADDEN: You want to have a driveway.


MADDEN: (Laughter) Yeah.

MAINO: And live, man. Live. Live. We don't have nothing else to prove no more. Everything else - everything that we proved, it's already proven, right? So it's like, how real can we keep it? How real do we want to keep it? No, it's already done. Live. Live.


MADDEN: In a sense, living is the one thing Bobby never got a chance to do.

CARMICHAEL: Because when labels prioritize your authenticity, your friends prioritize loyalty and the criminal justice system prioritizes convictions, it can be hard to remember that living should be your top priority.

MADDEN: And that's still about to be the case even when Bobby gets out. Earlier this year, his parole was denied. So instead of coming home this December, like fans had hoped, he'll be getting out in December 2021. And he'll spend the next five years on supervised release.

So when you get out, you're going to go back to rapping...


MADDEN: ...But you're not going to be in Brooklyn?


MADDEN: But you're still going to be at Epic?

BOBBY SHMURDA: Yeah. I'll be in New York to handle business or do a show. But I don't want nothing to do with New York.

MADDEN: What do you think is the biggest lesson you've learned out of everything?

BOBBY SHMURDA: That my Black ass should've started rapping since I was 10 or something.

MADDEN: You should've started rapping...

BOBBY SHMURDA: I should've started rapping before it. Yeah (laughter).

MADDEN: And never been in the streets?

BOBBY SHMURDA: Yeah. I'd have never been in the streets. You know what I mean? So a lot of people - my biggest regret is not following it earlier than I should have, not following my dreams earlier. Yeah.

CARMICHAEL: But in a sense, the streets gave you your flavor, too.

MADDEN: Right.

BOBBY SHMURDA: Yeah. It gave me a whole lot.

MADDEN: It gave you the story.

BOBBY SHMURDA: It gave me the story, the flavor, 20 hours in a cell (laughter) - you know what I mean? - dead friends, a bunch of shit. Yeah.


MADDEN: Hey, y'all. We're taking a break for the holiday. We'll be back with our next story in two weeks on Thursday, December 3. In our next episode, Isis Tha Saviour breaks down the ways women are written off in prison and in hip-hop. How can rap help heal carceral trauma?

ISIS THA SAVIOUR: Think about the music industry. It's really, like, only five labels in the world. And who owns them? Old white men funding Black toxicity.


MADDEN: This episode was written by me, Rodney Carmichael and Adelina Lancianese.

CARMICHAEL: Michael May edited this one, with help from Chiquita Paschal and Chenjerai Kumanyika.

MADDEN: It was produced by Adelina Lancianese and Dustin DeSoto, with help from Matt Ozug and Sam Leeds. Josh Newell is our engineer.

CARMICHAEL: Senior supervising producers are Rachel Neel and N'Jeri Eaton.

MADDEN: And shoutout to the bigwigs, Steve Nelson, Lauren Onkey and Anya Grundmann.

CARMICHAEL: Original music by Kassa Overall and Ramtin Arablouei.

MADDEN: Our digital editor is Jacob Ganz. Our fact checker is Jane Gilvin. Our lawyers are Kimberly Sullivan and Kaitlin Gurney (ph).

CARMICHAEL: And special shoutout to all our interns who helped make this trilogy possible over the last two years. Angela Velez (ph), Alec Cowan, Erin Slomski-Pritz, Sam Leeds and Babette Thomas.

MADDEN: Hit us up on Twitter. We're @LouderThanARiot. Rate and review us on Apple Podcasts. And to follow along with all the music you heard in this episode, check out the LOUDER THAN A RIOT playlist on Apple Music and Spotify now. And if you want to email us, we're at


CARMICHAEL: From NPR Music, this has been LOUDER THAN A RIOT.


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