“I don’t need this,” Alex Spiro says. “I could try bond trader cases where the bank pays you a million dollars, no one’s gonna argue with you, there’s no drama, no screaming, you try the case, you win, you move on. Or you lose and that’s unfortunate. You get a plea deal — they either take it or [they] don’t.”

Typically, Spiro would be the high-priced attorney representing a corporate client facing scrutiny from federal regulators. Or he’d be defending a major league athlete against misdemeanor charges of disobedience. Or else he’d be standing before a judge to defend a kid with rich parents against a DUI charge. Typically, Alex Spiro — a Harvard graduate, former CIA employee, and prosecutor turned defender — would be winning.

Instead, these days, Spiro is defending a client — the 21-year-old Brooklyn rapper Bobby Shmurda — who’s spent more than 500 days in jail as he awaits trial on an assortment of drug, gun, and conspiracy charges.

Shmurda’s infamous case presents quite possibly insurmountable challenges for the defense. It’s a Hail Mary. Acquittal is perhaps a lost cause. And as that trial approaches, Spiro is taking on yet another spectacular case: This week, former New England Patriots tight end Aaron Hernandez hired attorneys Jose Baez and Ronald S. Sullivan Jr., along with Spiro as a “trial expert” and forensic science counsel Linda Kenney Baden, to defend him against two counts of first-degree murder in the 2012 shooting deaths of two men near a Boston nightclub.

For Spiro, 33, it’s been a thrilling if difficult year. He’s preparing to try the biggest cases of his career, but neither trial — not Shmurda, nor Hernandez — will be Spiro’s first time defending a celebrity in the pressure cooker of a reporter-choked courtroom.

In the earliest hours of April 8, 2015, there was a stabbing outside the popular Manhattan nightclub 1 OAK. NBA player Chris Copeland was knifed in the gut. Club rats spilled into the street. Witnesses loitered, Atlanta Hawks players Thabo Sefolosha and Pero Antic among them. At the crime scene, where many bystanders were slow to disburse, one cop antagonized Sefolosha specifically. An argument erupted, and multiple New York Police officers kicked Sefolosha’s right leg from under him. They then dragged him back and forth between two parked cars, as if he were a rag doll. Multiple cops then drew their nightsticks and beat Sefolosha to the curb. (This is all on tape.) When he fell, he fell hard; just weeks before the playoffs were to begin, the cops broke Sefolosha’s leg. Later that day, Sefolosha stood on a fractured fibula before a judge to face arraignment on charges of obstructing governmental administration, disorderly conduct, and resisting arrest.

The Atlanta Hawks connected Sefolosha with a lawyer, Alex Spiro, an attorney at Brafman & Associates, a tall white man with a good suit, dark and slick hair, and a booming voice. “I’m not going to make this about, ‘It must have been because he’s big and black and in a hoodie,’” Spiro said in his closing statement at trial. He was doing a bit of reverse psychology, evoking the late Trayvon Martin and invoking the language of #BlackLivesMatter (a movement that Sefolosha had passionately supported in the months following Staten Island resident Eric Garner’s death at the hands of a police officer nine months before Sefolosha’s own beatdown and arrest). Spiro, careful not to demonize the New York Police Department before a jury but confident that the instigating officer was racially biased, outlined the series of provocations and intemperate miscommunications that led the cops to pursue and antagonize Sefolosha as he attempted to leave the scene, as instructed, in a cab.

At another point in his closing statement, Spiro insinuated that the instigating officer lied to investigators. He had denied Sefolosha’s assertion that the officer told the player “with or without a badge, I would fuck you up” before the altercation. The officer “doesn’t know what cards I’m holding,” Spiro said. “He doesn’t know if I have audio to disprove. He can’t just say no. He doesn’t want to say yes. He’s stuck. So he says, ‘I don’t recall.’”

In October 2015, a jury acquitted Sefolosha on all charges. Six months later, Sefolosha and Antic filed separate, multimillion-dollar civil suits against the NYPD and other city agencies. In the meantime, Sefolosha has pressed his case in the media. He’s spoken with multiple outlets about his rude and brutal encounter with New York’s finest — an encounter that left Sefolosha, instead of the cops, facing criminal charges. Sefolosha was the defendant, and yet Sefolosha and Spiro, together, put the NYPD on the defensive. What began as a standard misunderstanding between drunken clubgoers and humorless cops outside a nightclub became a case about race and police conduct in modern New York.

“Is this script right?” joked Roy Wood Jr., the correspondent on a Daily Show segment about Sefolosha’s case. “He got beat up by the police, went to court, and won. Oh my god!”

Sefolosha has retained Spiro in his civil suit against the NYPD to help him win Round 2.

Spiro represents the rich, the famous, and the restless. In November, he defended Cleveland Cavaliers player J.R. Smith after an unrelated altercation at the pizzeria next door to 1 OAK. In 2014, Spiro defended Robert Aaron, a jazz musician and friend of the late Philip Seymour Hoffman, who died of an acute mixed drug intoxication in his West Village apartment earlier that year. A detective stated that Aaron claimed to “rarely” sell dope to Hoffman, a charge that Aaron has denied. Ultimately, prosecutors dropped the most serious charge against Aaron (intent to sell heroin), who instead pleaded guilty to a lesser felony charge of drug possession and agreed to serve five years’ probation. Spiro saved Aaron (full name: Robert Aaron Vineberg) from his worst possible sentence, prison time and possible deportation back to his native Canada, if he’d been convicted of selling.

Aaron, recalling Spiro’s counsel at this particularly dark time in his life, says the attorney was a real, live Perry Mason. “He knows everybody. He knows every trick. He’s so on top of the game. He’s always in control of the ball.”

Spiro is the alpha, the ace optimist who smirks and gestures with utmost confidence in his faculties. “People come in here and tell me stories of what happened on the night in question. About how it all went wrong,” Spiro says. “I feel like I’m good at figuring out why it all happened, whether it’s true, what the answer is, and how to find your way out of the cave with just one small point of escape.”

In our earliest correspondence, Spiro asks me to meet him at a swanky midtown steakhouse. He talks like a guy who’s never left the East Coast. Just reading court transcripts of his oral arguments, you can hear the brawny hints of New York, where Spiro was born, and Boston, where his parents raised him and his three siblings.

Spiro studied psychology at Harvard. His father suffers from multiple sclerosis, so he was initially motivated to become a doctor. After working with adolescent Asperger’s patients at McLean Hospital during his undergraduate term, Spiro retrained his focus from medicine to law. “As I found myself around doctors and lawyers a little bit more, it seemed to me that my skill set would be better served, and I would be better at being a lawyer,” he says. “Or maybe I just wanted change.”

Indeed: In 2007, Spiro graduated Harvard Law School and joined the CIA. He worked in Langley for a year before colleagues and alumni advisers referred him to the Manhattan District Attorney’s Office. “I didn’t go to law school with a particular leaning between defense and prosecution,” he says. “I wanted to be in a courtroom. I wanted to advocate. I wanted high stakes.” And, of course, he wanted to win.

For four and a half years, Spiro worked as a prosecutor. He tried murder cases. He convicted those he called some of “the most dangerous men in the city.” He resolved a 41-year-old case in December 2012, when Rodney Alcala, the “Dating Game Killer,” pleaded guilty to the murders of two New York women six years apart. David Moreno, a criminal defense attorney who worked alongside Spiro in the DA’s office, admired Spiro’s junior hustle. “This guy had been there for two or three years, and there he was every week trying big cases,” Moreno says. “The way homicides are handled in Manhattan, the people in charge have all been in the office anywhere from eight to 30 or 40 years. As a third-year, Alex was on that chart. He kinda forced his way onto it. There was cases in that office that nobody wanted, and he said he’d handle them. He got assigned to them, he rocked it, and then he was on the chart.”

Spiro advanced. Then, in July 2013, the illustrious Benjamin Brafman poached him to work for the accused instead. As an attorney at Brafman & Associates — a pricey, white-collar firm with offices in midtown Manhattan — Spiro typically represents clients who live at the bleeding edge of privilege. Last year, the family of Kathleen Durst, the first wife of notorious real estate heir Robert Durst, hired Spiro for representation in a $100 million wrongful-death claim against the Jinx subject related to Kathleen’s unsolved disappearance in 1982. (As of June 2016, the lawsuit is yet to go to trial.)

Based on the strength of his personal record and Brafman’s reputation, Spiro says, he’s hounded by referrals. There’s no ambulance to chase, he insists, no press conference to call. The cameras find his potential clients just as the clients are finding him.

Spiro’s trickiest pending case is that of the incarcerated rap star Bobby Shmurda — real name Ackquille Pollard — a 21-year-old Brooklyn rapper who stands accused of eight assorted charges, including gun possession, conspiracy, and drug paraphernalia use.

For Spiro, Bobby Shmurda isn’t a typical client. The rapper’s breakout song, “Hot Nigga,” is a survivalist boast of a kid and his rap crew GS9’s Brownsville clout. The song blew up on the strength of a viral Vine clip, cut from a $300 music video, in which Shmurda throws his fitted cap to the sky and shimmies among onlookers. In summer 2014, as “Hot Nigga” was climbing the Billboard Hot 100, Epic Records signed Bobby Shmurda to a recording contract reportedly worth more than a million dollars.

Bobby Shmurda rode high for about five months before the NYPD arrested him and 14 other GS9 affiliates on 69 felony counts, including murder, assault, weapons possession, reckless endangerment, and criminal conspiracy. In a press release outlining the indictment, New York Special Narcotics Prosecutor Bridget G. Brennan described the Brownsville crew’s alleged criminal behavior as “an escalating pattern of violence spreading from their home community of Brooklyn to South Beach, Florida.” Brennan and New York Police Commissioner Bill Bratton — who recently disparaged “so-called rap artists who are basically thugs” following a backstage shootout at the popular Manhattan concert venue Irving Plaza — presented the charges and much of the physical evidence against GS9 in a dramatic, televised press conference. A judge trumped the rapper’s fresh, million-dollar recording contract with a $2 million bail requirement. Shmurda and his family have pulled together several bail applications, with various funding arrangements, for consideration. The court has rejected them all. After more than 500 days in jail and a half dozen bail hearings, Bobby Shmurda has yet to face a jury of his peers.

With his trial most recently postponed to September 12, 2016 — that’ll be 635 days after his arrest — Shmurda now sits in Rockland County Correctional Center, 40 miles north of New York City. “Pretrial detention is one of the major problems with our system,” Spiro says. “The presumption of innocence is a piece of gum we walk over, not the statute that hangs above us as it should be.”

In Sefolosha’s famous case, the abundance of camera-phone footage and testimony from Sefolosha’s teammate Antic favored the defense. In the GS9 case, however, there’s a landslide of evidence against the crew, including Rikers Island phone taps and 21 confiscated guns. As much as Spiro resents Shmurda’s predicament, I’m sure he also resents his own odds at trial. “I never became a public defender, but I feel like a public defender right now,” Spiro says. “It’s unbelievably trying.”

Spiro says that the judge, the prosecutor, and the media have all wildly overestimated Bobby Shmurda’s criminal intent. “The kids with the concrete shoes are washing up in Brooklyn, and they put Bobby Shmurda back on the news as if it has anything to do with him,” Spiro says, referring to reports last month that Brooklyn resident Peter Martinez, a Crip who had been missing since February, was killed and dumped in Sheepshead Bay, where his corpse recently washed up fitted with concrete. The abundance of charges and evidence leaves little hope for exoneration. In April, a jury convicted GS9 members Rashid Derissant and Alex Crandon of second-degree murder for the death of 19-year-old Bryan Antoine in a 2013 gang shooting in Brooklyn. Derissant got 98⅓ years to life. Crandon got 53⅓ years to life.

Bobby Shmurda will not plead guilty to any of his charges. His bail is stuck at $2 million. Shmurda’s case, with charges falling under the jurisdiction of New York City’s Special Narcotics Prosecutor, will be tried in Manhattan. “We pulled the census,” Spiro says. “Brownsville is 99.9 percent African American and Caribbean, less than 1 percent Caucasian. And he’s gonna be tried by an all-white jury.” At this point, Shmurda’s family trusts no one, and they see little difference between a four-year bid if Shmurda did strike a deal and a far longer term if a jury convicts him of all his charges. Either way, the momentum of Shmurda’s rap career has been squandered. All his recording contract has afforded him is the best lawyer money can buy.

All that’s left for Bobby Shmurda, then, is the potential spectacle of a criminal trial in Manhattan. In a city where the criminal courts held the late Kalief Browder at Rikers for a thousand days without due process. In a nation that has, more than 20 years after the act, gladly resurrected the spectacular minutiae of the ancient O.J. Simpson murder case. But in a system that’s fascinating at televised distance but tedious up close, a charismatic and telegenic attorney is perhaps the best defense against certain institutional disadvantages. Gloria Allred, who bills herself as a “discrimination attorney,” has famously — controversially — courted causes célèbres since the U.S. Supreme Court decided Roe v. Wade in 1973. The late Johnnie Cochran, who represented O.J. Simpson and 2Pac in their notorious criminal trials, was once a quite polarizing figure — not simply the celebrated underdog of American Crime Story.

In a 1997 profile of Cochran, the Los Angeles Times wrote that “as he becomes more visible [in New York], Cochran also becomes more vulnerable to the kinds of attacks that focus on him as a celebrity lawyer who takes fewer underdogs and more high-profile clients.” For Alex Spiro, the GS9 case is a Gordian knot of both client types, Shmurda being a celebrity but also an underdog who will likely lose a few more years of his life at trial. Spiro, for all his passionate discussion of justice, mostly just loves to win.

At trial, Spiro says, a great attorney will be “entertaining, deep, and persuasive,” which is to say: captivating. The broad audiences for 24/7 cable news coverage require spectacle to win their attention and tension to sustain it; jurors, too, require such captivation, lest apathy and fatigue mire their deliberations. It turns out that even the most comprehensive recitation of stats and biases will get you only so far.

Lucky for his defendants, Alex Spiro gets a thrill out of juries. “When I stand up and start addressing them,” he says. “I’m hoping they think, ‘This might be interesting. This might be important.’

“‘This might be something I want to stay for.’”

An earlier version of this piece incorrectly stated that Alex Spiro got Rodney Alcala to confess to the murders of two women. Alcala pleaded guilty to the two murders.