On March 20th, inside the high-security wing of Los Angeles’ Clara Shortridge Foltz Criminal Justice Center, the man once called “the most feared man in hip-hop” is looking more like the 50-year-old with chronic health issues that he is.

Suge Knight sits in shackles, wearing an orange prison jumpsuit and chunky glasses, his beard flecked with gray, listening impassively. It’s the end of the day’s proceedings, and Judge Ronald S. Coen is announcing the bail for Knight, who is facing charges of murder, attempted murder and hit-and-run: “In this court's opinion, $25 million is reasonable, and it is so set.”

A gasp erupts from Knight's row of supporters — some of whom sport red clothing or accessories, a color associated with the Bloods and Piru street gangs. The most shocked are Knight's family, who have attended nearly all of his court dates: his parents, along with his fiancee, Toilin Kelly, and sister Karen Anderson. “He’s never had a bail like that before!” Anderson exclaims.

As attendees exit and Knight is escorted out by the bailiffs, Knight’s attorney Matthew Fletcher pleads with Coen to reconsider. Fletcher points out that Knight has been held in solitary confinement for nearly three months, with next to no contact with family or friends. (“They wouldn’t allow this at Guantánamo Bay,” Fletcher says.) The lawyer goes on to complain about Knight’s treatment in jail for his numerous medical ailments, which include diabetes, blood clots and impaired vision.

The judge is unswayed, especially by Fletcher’s pleas about Knight’s poor health. “He was offered food and refused it,” says Coen. At that moment, as if on cue, Knight re-enters the courtroom, and suddenly collapses, his 300-pound-plus frame tumbling forward onto the padded chair he was just sitting in minutes earlier. Outside, Knight’s supporters have started a protest. “This is a public lynching!” shouts a woman in a red dress and blond Afro. “Black lives matter!” The painful irony is that Knight is being prosecuted for murdering a black man — a man he once called his friend — and seriously injuring another.

This could finally be the end of the road for the record-label head who, a generation ago, helped bring the West Coast gangsta rap of Dr. Dre, Snoop Dogg and Tupac Shakur to the mainstream, pushing aside the pop rap of artists such as MC Hammer and Tone-Loc and putting low-riders and gang signs into heavy rotation on MTV.

In the process, Knight established himself as a legendary music-biz tough guy. His exploits — some mythic, some real — during the heyday of Death Row Records have become part of hip-hop lore: In the early Nineties, he allegedly shook down Vanilla Ice into handing over publishing profits, walking the rapper out to a hotel-room balcony to show him how far his fall would be. ("I needed to wear a diaper that day," Ice said later.)

In his memoir, former N.W.A manager Jerry Heller alleged that Knight and his cohorts, bearing baseball bats, intimidated Eazy-E into releasing Dre from his Ruthless Records contract. (The claims have never been substantiated.) Knight was sitting next to Tupac when he was gunned down in 1996 in Las Vegas; his participation in a fight on the night of the shooting would land him in prison for five years on a probation violation.

As Knight’s fortunes have crumbled, he’s gotten closer to the streets, according to prosecutors. In a motion arguing for the high bail (which would later be reduced to $10 million), the L.A. District Attorney’s office alleged a recent scheme by Knight to “tax” out-of-town rappers for as much as $30,000 just to work in Los Angeles and Las Vegas. Last year, Knight called out Rick Ross in a video interview: “You know you owe that bread, titty man,” Knight said. “I’m gonna beat the dog shit out of you.” His targets aren’t limited to big fish — in 2014 he was caught on surveillance punching a worker at an L.A. medical-marijuana dispensary after being refused service for lacking documentation.

Knight hasn’t been charged for any of the above episodes; his current lawyer Thomas Mesereau says, “He never threatened Vanilla Ice,” and that all the claims of extortion are based on “a lot of gossip and innuendo.” But former associates struggle to understand why such an undeniably talented businessman can’t escape this kind of small-time drama and thuggery. “I watched Suge decline the last 10 years,” says Cash Jones, a.k.a. Wack 100, a former Death Row “foot soldier” who now manages Ray J and the Game. Knight already has two prior violent felonies on his record: If any of his current charges stick, under California’s Three Strikes law, he could be going to jail for the rest of his life.

“Suge lost focus of the business, and who he is,” says Jones. “He could’ve been a lot of things, but he chose not to.”

Knight’s most recent troubles apparently began like many Suge Knight stories: with him thinking that somebody owed him money. The upcoming N.W.A biopic, Straight Outta Compton — co-produced by Dre and Ice Cube, and due out in August — was getting attention after a teaser leaked in December. “People working on the set were calling and telling Suge, ‘Hey, man, this movie is really [becoming] a Death Row movie,’ with a Suge look-alike in the movie beating up people in the studio and all that,” says Reggie Wright, a childhood friend of Knight’s who worked at Death Row from 1994 to 2002. “Suge felt like they were using his likeness in this movie without consulting him.”

On the afternoon of January 29th, Knight drove up to the production’s base camp in his red Ford Raptor pickup, breezing past the film’s security. Dre’s bodyguards would not move him while Knight was on the premises, leaving producers in a panic. Cle “Bone” Sloan – a “nonactive” gang member who was working as a technical adviser to the movie – stepped in, confronting Knight. Sloan said later that he had heard there was a “problem” between “[Knight] and Dre or somebody.” The confrontation turned into a shouting match. Sloan said he told Knight, “Why don’t you leave so we can move forward? You got the white folks scared!” Eventually, Knight left the set.

Shortly after clearing out, Knight received a call from a respected South Central entrepreneur named Terry Carter who was at the shoot that day and was perhaps hoping to mediate the dispute. Carter, 55, was a self-made man who, after losing his mother and brother in the space of a year when he was 18, had built businesses in music, cars and real estate — most notably co-founding Heavyweight Records with Ice Cube in 1998. “Ice Cube and Dre would come by the house like it was nothing,” says Carter’s daughter Nekaya about her childhood. Carter was a family man, with three children; he had also taken in his sister-in-law’s five kids when she couldn’t care for them. People who knew Carter call him a “peacemaker.”

There are different accounts of Knight’s relationship with Carter. His daughters say that he and Knight had done little more than “cross paths,” but Knight’s friend and bail bonds agent Jane Un says that Carter and Knight were “friends” and had even “explored going into business together.” Carter was now requesting Knight’s presence at a Compton burger joint, Tam's, a few miles from the movie’s base camp.

Minutes later, Knight pulled up outside the Tam’s parking lot, where Carter and at least one other man had already gathered. According to Sloan’s interview with police, Knight started bad-mouthing Sloan — just as, unbeknownst to Knight, he pulled up. “He was talking shit,” Sloan recounted, “and I just popped out like a jack-in-the-box.” Sloan came at Knight saying, “Let’s do it!” and began throwing punches at Knight through the Raptor’s window.

“Every day, I try to forget it,” Sloan said later. “I screwed up, and Terry’s dead.” Knight turned himself in to police about 12 hours later, around three in the morning. Knight’s initial counsel in the case, James Blatt, told the Los Angeles Times that Knight was “heartbroken” over Carter’s death. A subsequent lawyer, Fletcher, has suggested that Carter helped lure Knight into a deathtrap. Carter’s friends and family are still deep in mourning. “It was a tragedy,” says Lydia Harris, an early Death Row partner. Nearly 2,000 people attended Carter's funeral.

Knight’s strategy will almost certainly be self-defense. But even if he wins, he is facing another case, which has received less media attention, but may prove harder to beat. Last September, Knight and comedian Katt Williams were leaving a Beverly Hills studio when they encountered celebrity photographer Leslie Redden. Believing Redden had photographed Knight’s son without permission, Knight is alleged to have told her he had a “bitch” who was going to beat her “motherfucking ass,” and to have shown Redden his waistband. Redden fled, but was stopped by Williams and an unknown woman, who allegedly knocked the photographer to the ground and took her camera. In addition to criminal charges against Knight and Williams (who have both pleaded not guilty), Redden has also filed a civil suit against Knight, alleging severe injuries to her back, head and neck.

“It don’t matter if it’s $100 or $100,000,” says Cash Jones, “when you take somebody’s property and harm them in the process, it’s robbery” — a felony charge that could also put Knight away for years. “Suge was already out on bail for that case, and now he has this hit-and-run situation — and there’s video of it that’s not in his favour. He’s over with.”

“He was always the same guy,” says Wright, “boisterous, a bully.” Marion Hugh Knight Jr. grew up on the east side of Compton, in what was, by all accounts, a strong, loving family. “The irony is that you would think this guy comes from a broken home,” says former Death Row publicist Jonathan Wolfson, “but his parents have been married to this day, and they are the nicest.”

“Suge’s daddy was lovely!” says Knight’s ex-girlfriend, the R&B singer Michel’le, talking about Marion Knight Sr. and mother Maxine. “Oh, he’s just a dream. His mother is nice too, but she has a mouth on her like Suge: She’d curse you out one minute and then go, ‘Well, you know, baby, it’s OK’ the next. Suge is a mama’s boy, definitely.” Many who have dealt with Knight cite his keen natural intelligence. “Suge had huge potential,” says Wolfson. “He could’ve done anything — he was a force.”

A charismatic, gifted athlete, Knight wanted more than his parents’ two-bedroom home. “As soon as I was old enough,” he told The Guardian in 2001, “I told myself that I’d never live or end up dying in a place like that. I made up my mind that I wanted everything, and nothing would stop me.” Knight started playing on the Lynwood High football team; he was fast as well as strong. “I remember our coach chastising me because Suge beat me in a race, and I was a running back, and he was a lineman,” says Wright. Knight said that he would shake down wealthy white kids outside their Hollywood high schools, but he was more of an alpha-male football player than a hoodlum as a teenager. “He had twin cousins, Ronald and Donald,” says Wright, “and they pretty much ran Lynwood High School.” His neighbourhood was a Piru Bloods zone — Knight has said he sometimes saw bodies in the alleys on the way to school — but “gangbangers didn’t mess with the athletes,” says Wright.

Knight had two impressive seasons at the University of Nevada-Las Vegas, and a short-lived NFL career, going undrafted but making it onto the Los Angeles Rams as a replacement player for two games during the strike season of 1987. That same year, he shot a man in Las Vegas while allegedly trying to steal his car, and was arrested for attempted murder. Knight pleaded no contest to a misdemeanor and was put on probation, but his pro football career was over.

Interestingly, Wright attributes some of Knight’s unpredictability and rage to diabetes, which has shadowed him throughout his life. “A lot of people don’t know Suge has diabetes real bad,” Wright says. “He doesn’t have the correct medication to treat it, or go to the doctor to get it controlled correctly. So a lot of the times when he gets angry, it’s because his sugar is up.”

With the door to the NFL closed, Knight used his size to get into the music business, working as a bodyguard for Bobby Brown. Knight began moving in the same circles as rapper the D.O.C., as well as Dre, Eazy-E, Cube — and a young MC named Mario Johnson, who complained that he’d written much of Vanilla Ice’s To the Extreme. Knight saw his opportunity, which supposedly led to the notorious hotel-room confrontation with the white Florida rapper. Ice settled with Knight for an unspecified amount. It was his first big payday.

The next breakthrough came when D.O.C., Dre and Knight hatched a plan to get the rappers out of their contracts with Heller’s Ruthless Records. Death Row was founded in 1991, and the next few years were gilded with hits: Dre’s 1992 classic The Chronic went triple-platinum, followed by Snoop Dogg’s quadruple-platinum Doggystyle. In the space of a few years, Knight had inserted himself into the heart of West Coast hip-hop and taken over.

Michel’le, who was signed to Ruthless and then Death Row, says that things began to sour between Knight and Dre when Tupac came into the picture in 1995. Knight felt that Dre didn’t have Tupac’s gung-ho work ethic; Shakur would become both Death Row's commercial focal point and Knight's close friend in a way Dre never was. At the same time, Knight began to feel disrespected by the superstar producer. “Dre did not want to listen to Suge, and that bothered him,” Michel’le says. “Suge was like, ‘You were getting two cents a record [with Eazy-E and Heller], but I helped you make real money.’ ”

In 1996, Dre split with Knight, forming his own label, Aftermath — like Death Row, under the umbrella of Iovine’s Interscope Records. Knight was relentless in trying to get back master recordings that he believed belonged to Death Row. According to Randall Sullivan’s Labyrinth, Knight talked his way onto Dre’s property claiming to be Iovine: “When he opened the door, Dre said, ‘In comes Suge with eight or nine niggas,’ ” demanding the tapes.

Both friends and foes agree that Knight never quite recovered from his five-year prison bid, which started in 1996.

When Knight got out of prison in 2001, “He was different,” Wright says. “And he was more notorious than ever.” Knight quickly returned to the high-roller lifestyle he’d enjoyed in the Nineties. “There was a lot of partying — in New York, Houston, Chicago, Malibu, staying at the Four Seasons in Hawaii,” says Crooked. “We took Suge’s yacht out a couple of times and got DJs and caterers on there, called up some well-known strippers. We spent a lot of time just enjoying life.”

There were signs that the party was going to end. Death Row had split with distributor Interscope in 1998, which meant less of a financial safety net.

Knight’s dreams of restoring Death Row to its former glory soon fizzled. Not long after he got out, “He said, ‘Let’s go to New York — we’ve got to let the world know that we're back!’ ” says Crooked. “So we hit the media trail very hard — went to all the main stations, all the magazines, everything. It just felt like, ‘OK, it’s about to pop off.’ ”

It never did. “Crooked was one of the hardest rappers on the West Coast back then — lyrically, he could stand with anybody,” says Jones. “But he had no distribution — and, ultimately, no album on Death Row.” Nearly all of the label’s projects from that era suffered similar fates.

“A lot of people didn’t want to see Suge succeed,” Crooked says. "People were intimidated by him. The ball would start moving, and then it would just stop dead.”

“No one wanted to do business with him,” says Jones. "He had no artists, radio showed him no favours, his office building was in foreclosure, and there were all kinds of tax liens and lawsuits. He had to revert back to what he knew — which was the block.”

“We were getting into brawls, and our CEO was throwing punches too,” Crooked says.

At the 2004 Vibe Awards ceremony in Santa Monica, Knight allegedly paid an associate to punch Dre as he prepared to accept a lifetime achievement award — after which Dre’s attacker was stabbed, apparently in retaliation, by G-Unit rapper Young Buck. (Buck was sentenced to three years’ probation; his victim suffered a collapsed lung; Knight was investigated but never charged.) “We were at the Vibe Awards for one reason and one reason only: for a problem,” admits Jones, who attended the event alongside Knight.

The authorities, meanwhile, were keeping an eye on Knight and Death Row. “There was pressure from the police,” Crooked remembers. “If you were on Death Row, your car and house were definitely marked. A cop would just knock on your door and say, ‘We’re just checking on you. We know you Death Row rappers, we know how you all like to live.’ ” One day in 2002, the L.A. County Sheriff’s Department stormed the label’s office in a morning raid involving a gang-related homicide. “They made everyone get on the ground,” Crooked says. “Then they cut up the ceiling and took all the computers.” Crooked had enough: “I’m an artist. I got tired of living this lifestyle and not putting out music.” (Crooked is currently signed to Eminem’s Shady Records as a member of rap supergroup Slaughterhouse, and also performs as a solo artist.)

The final blow for Death Row came in 2005, when Lydia Harris was awarded a staggering $107 million damages judgment. Death Row had been started with money from Harris’ then-husband, imprisoned drug dealer Michael “Harry O” Harris. But her reasons for suing Knight were personal as well as financial. “Years had gone by, and then Suge got on national TV, saying that I slept with so many guys,” says Harris, who was also awarded damages for defamation of character as part of the larger lawsuit.

The following year, Death Row declared bankruptcy, and the label’s assets were eventually liquidated and sold. “They auctioned off everything,” Crooked claims. “They even sold Suge’s boxer briefs that they found in the penthouse suite on top of the Death Row building! Here was one of the only African-American men to own a major building on Wilshire Boulevard, and they sold the man's fucking drawers. That either inspires you to get up and create something even bigger — or you crumble up inside and become bitter.”

Knight’s finances have never fully recuperated. He was recently in negotiations to sell his life rights for film, TV and technology projects to a company called Everlert. Its president, Mark Blankenship — a Yale-educated former attorney and one-time Republican congressional candidate who sports a long braid down his back — says that, thanks to Knight’s latest ordeal, those life rights are becoming “more and more valuable every day.” But in the meantime, Blankenship says that Everlert had to help pay the school tuition for Knight’s young son Legend.

According to Wright, the bankruptcy “broke the man down.” Knight was busted for marijuana possession in 2005 (the charge was later dropped), and in 2008 he was arrested for beating his then-girlfriend Melissa Isaac while in possession of Ecstasy and hydrocodone. (Knight pleaded guilty to misdemeanor battery, was charged a $340 fine and ordered to undergo counseling.) “Suge didn’t do drugs back in the old days — he didn’t smoke marijuana, or anything,” Michel’le claims. “All he'd do was have a glass of champagne to toast with at celebrations. That was it.”

Knight’s ongoing embrace of the thug life may have destroyed any remaining credibility he had as a businessman. “When it comes to the Piru shit, he should’ve stepped away a long time ago,” says Jones. “Instead, he got neck-deep into it.” With proceeds from Dre’s chart-topping hits a distant memory, and no new breakthrough artists to profit from, Knight has apparently had to find alternative sources of income. “Suge had to go back and adapt to what he knew: going around and getting money from people that he felt owed him,” Wright says. In 2007, when a reporter for The Washington Post asked Knight how he still had money, he preferred to evade the answer rather than lie. “I don’t lie,” said Knight. “The only people I lie to are the police.”

Meanwhile, Knight’s former circle is debating the outcome of his current situation. “The lowest I can see him getting, realistically, is 20 to 30 years,” says Jones. “Worst-case scenario, he’ll get life. Either way, he’s out of business.”

After hiring and firing a number of lawyers in rapid succession — including Fletcher and, for a brief reunion, Death Row’s infamous legal consigliere in the Nineties, David Kenner — Knight has recently retained the powerful Mesereau, who successfully defended Michael Jackson in his 2005 child-molestation case and has represented controversial figures ranging from Mike Tyson to actor Robert Blake. “I am convinced of Knight’s innocence, and I am convinced these cases should not have been filed. I look forward to defending him,” Mesereau told Rolling Stone. “All I am going to say at this point is that he was defending himself at all times, and should not be facing any charge of murder, attempted murder or hit-and-run. If I had been driving the truck, I would not even have been charged with a misdemeanor. And as far as his robbery case goes, it’s utterly ridiculous.”

As many of his associates have noted, Knight has gotten out of seemingly impossible situations before. “I still consider Suge a friend, but I can’t deal with that nigga — he’s crazy,” says Wright. “He’s been knocked out three or four times, and he's still walking and talking like he’s the baddest brother around. He’s got some wiggle room, though. Don’t count him out yet.”

“The Suge Knight story has twists and turns, don’t it?” Crooked says. “We don’t have any clue how it will end. He seems to think that he’ll be back on the streets.”

Crooked goes on to relate a story about the day that Knight turned himself in to police.

“He was smoking a cigar, and he put it up in a tree,” says Crooked. “Then he said, ‘I’ll get back to that.’ ”

•Excerpted from Rolling Stone magazine. Photo shows fallen rap mogul Suge Knight in prison uniform.