On a Monday morning around this time in 2016, Chris Brown woke up and sparked a blunt. He had fallen asleep on a bright red sectional sofa in the living room of his $4.35 million mansion in Tarzana, an affluent area of Los Angeles’ San Fernando Valley. It’s where he would pass out most evenings. Lately, says a former employee who was accustomed to scenes like this, Brown had trouble sleeping in his master bedroom upstairs and would instead watch sci-fi movies all through the night. Empty Styrofoam cups littered the table, a sign that Brown -- who hadn’t been taking his medication for the bipolar II condition he had been diagnosed with in 2014 -- had likely also been sipping lean (a mixture of promethazine/codeine syrup and a soft drink), his comedown of choice after a coke or Molly binge. Brown scrolled through Instagram, hunting for clues about the status of his ex, the 28-year-old model Karrueche Tran. Whom was she with last night, and where? Who was commenting on her most recent photos?

A delivery man arrived and began ringing Brown’s doorbell. “Do your f—ing job!” barked Brown at one of his security guards, a hulking man who had been living for the past three-and-a-half years in the home. But the guard, who was off duty, was asleep, and his partner was outside. Like many other nights, the guard had stayed up late to check Brown’s pulse. The bell rang again — this time, it was a construction worker who had been employed at the house all week. Brown paced back and forth. Finally, he lost his temper. “I’m going to show you what it’s like not to work with Chris Brown for two weeks!” he shouted at the guards, kicking them both out of his house.

At this time, Brown was preparing for the European leg of his One Hell of a Nite Tour, but, according to various members of his team at the time, he would stay up for as long as three days in a row, snorting cocaine and dabbling in Xanax, marijuana, Molly and lean. By the time he finally left for Europe in May, according to a lawsuit filed in June, he had physically attacked his longtime manager, Michael “Mike G” Guirguis. (In the suit, Guirguis also claimed that in the four years they worked together Brown suffered from “addiction, anger control and violence issues.”) In August, Brown was arrested after he returned from the tour, following a standoff with police at his home for allegedly pointing a gun at the actress Baylee Curran. He also, TMZ reported, threw a duffel bag full of drugs and weapons out of his window. (Brown’s lawyer, Mark Geragos, later disputed that claim, and to date, no charges have been filed. Both Brown and Geragos declined to comment for this story.)

Brown’s problems are no secret. Since his brutal attack on then-girlfriend Rihanna in 2009, which sent her to the hospital bloody and bruised on Grammy night, it seems like there’s nothing he can do to shock the world -- or alienate his Team Breezy fan base, which can be as belligerent and defensive as the singer himself. (Brown has had to ask his fans, on occasion, to stop threatening to kill his critics.) Since that assault -- for which he was sentenced to six months of community labor, a year of counseling and five years of probation -- Brown, 27, has been arrested two more times and made two trips to rehab, getting kicked out both times.

Through the years, Brown has descended from the height of stardom to the lowest circle of fame, becoming better known as a sleazy tabloid obsession than a VIP. He has made news the last few months for a variety of unsavory reasons: writing “Somebody tell Aladdin hop off my dick” when Aziz Ansari compared him to Donald Trump on Saturday Night Live; the discovery of his $500,000 Lamborghini Aventador, abandoned on Coldwater Canyon in Beverly Hills, apparently demolished in a high-speed crash (and reportedly driven by one of several friends to whom he had given keys); the saga of his now-canceled boxing match with Soulja Boy, who said he had earned Brown’s ire by liking a picture on Tran’s Instagram; and the restraining order Tran filed for on Feb. 17, claiming that Brown physically abused and threatened to kill her.

Still, while it seems as if Chris Brown the man has yet to find his bottom, Chris Brown the R&B star remains a commercial force and near-constant presence on radio, through songs of his own and features on recent tracks by of-the-moment artists like Gucci Mane and Jeremih. In 2016 alone, he managed seven debuts on the Billboard Hot 100, with “Back to Sleep” peaking at No. 20. And despite an Australian leg that Brown was forced to cancel (after the government warned that it would deny his visa due to his criminal conviction in the Rihanna case), the One Hell of a Nite Tour played 41 shows at arenas across the United States and Europe. Brown has already scored one Hot 100 hit this year -- “Party,” featuring Usher and Gucci Mane, which reached No. 40.

“Chris is an incredible singer and stylist who knows exactly who he is as an artist,” says Brandy, who featured Brown on her 2012 single “Put It Down.” “As a whole, he’s courageous. I loved working with him and would like to work with him again.”

After he released his first album at age 16, 2005’s Chris Brown (which has sold 2.3 million copies in the United States, according to Nielsen Music), the artist didn’t merely become a reliable hitmaker -- he was hailed as the next Michael Jackson. His first-ever performance at the MTV Video Music Awards, in 2007, was an instant classic: He leapt between platforms, flawlessly executed pratfalls and even slipped an ultra-precise snippet of Jackson’s “Billie Jean” choreography into a marathon six minutes onstage. (Rihanna showed up to sing “Umbrella” partway through.) “He’s the most all-around talented person in R&B,” says Ebro Darden, assistant program director/morning host at WQHT (Hot 97) New York. “Trey Songz is talented, but he can’t dance like Chris Brown. Usher is probably the only person who could rival him, but he doesn’t have the songwriting abilities Chris Brown does.”



“He’s a natural. He is almost God’s perfect person,” says Flii Stylz, Brown’s longtime choreographer, who previously worked with Usher. “No matter how he f—s up and no matter what he does, another replacement for him is not on the way in the next decade.”

It may be true that there’s no replacement for Brown. (And in fact, the new generation of rapper-singers like Drake and Bryson Tiller may have rendered the classic R&B singer-dancer nearly obsolete.) But that hasn’t turned Brown -- who, since at least 2014, has sometimes publicly claimed affiliation with the Bloods gang -- from his self-destructive path. And his career now exists in a kind of purgatory. His label, RCA Records, remains supportive of Brown, saying in a statement to Billboard, “We’re proud to be in business with Chris, a uniquely gifted artist who is always striving to be better. Through his ups and downs, we will continue to stand behind him.” But since Guirguis’ departure in May 2016 and publicist Nicole Perna quitting that spring, Brown has worked without a personal rep or manager. RCA has yet to give a release date for his next album, Heartbreak on a Full Moon, which was announced in May 2016. (The label says it is “targeting this summer” and that Brown is still recording.) And there’s no indication of when and where his Welcome to My Life documentary may air, even though a trailer was posted online in April 2016.

On Feb. 22, Brown announced an ambitious spring tour, Party, with 33 dates planned at arenas across the United States and Fabolous and 50 Cent among the special guests. But if his last run of dates -- during which, according to someone who was then working closely with him, he threatened his tour manager in a rage, leading her to quit -- is any indication, life on the road offers no escape from the anger and addiction that haunt him. “He will cuss you out and say, ‘Hey, man, I’m functioning. I’m going to get the work out.’ And he does,” says a current member of Brown’s team. “But [he’s not] the first functional star who thinks they can handle those powerful drugs. I got to say with all my heart, he’s dancing with death.”

Not long ago, it looked as if Brown might turn things around. In early June 2014, he had just been released early from a Los Angeles County jail. (The previous October, Brown had violated his probation by punching a man in Washington, D.C., who was allegedly trying to take a picture with him.)

Three days after Brown’s release, Tran, his girlfriend at the time, led him, blindfolded, into a backyard barbecue she had organized with Guirguis at a Beverly Hills mansion. (Tran, a petite part-Vietnamese, part-Jamaican Wilhelmina model, started dating Brown in 2011, although after trading digs with Rihanna on social media, she and Brown broke up and Brown and Rihanna briefly reunited. She and Brown reconciled in 2013.) Brown’s mother, Joyce Hawkins; T-Pain; Wiz Khalifa; Tyga; Amber Rose; Akon; and various executives from his label, RCA -- including president of urban music Mark Pitts, who has worked with Brown since signing him at Jive Records -- greeted Brown. According to two guests who were there, the singer clapped his hands, took a bow and kissed Tran on the lips. “I love you so much,” he said.

Earlier that year, a report by Brown’s probation officer surfaced, revealing he had been diagnosed with bipolar II disorder, a condition defined by depressive and hypomanic episodes (the latter less extreme than typical “mania”) and often triggered by periods of extreme stress and drug and alcohol abuse. The report also cited “untreated PTSD” and “inappropriate self-medicating.” But at the party, Brown seemed clean, happy and focused. “When he got out of jail, that is the best I’ve seen him,” says Stylz (although, he adds, referring to Brown’s weight gain, “he looked like Sinbad”). Around that time, says Stylz, Brown “would sit down and meditate. I liked that Chris, who meditated when he was frustrated.”

Indeed, Brown was in a reflective frame of mind when he gave Billboard his first post-jail interview that August. (His album X would debut at No. 2 on the Billboard 200 a month later.) He allowed that, before going to jail, “maybe I was out of control. Or I needed something to humble me to the point where I get it.” In November, he told Darden in a Hot 97 interview that prior to jail, he used “the syrup, the Xanax,” and added that while marijuana offset his hyperactive tendencies, “once I started doing the lean, the other stuff ... I’d be sitting in the [recording] booth sleeping.” In the trailer for the unreleased documentary, he admits that, following the Rihanna incident, “I felt like a f—ing monster. I was thinking about suicide and everything else. I wasn’t sleeping. I barely ate. I just was getting high.”

Still, when confronted with past mistakes, Brown had often responded with violent outbursts -- like the time on Good Morning America in 2011, when host Robin Roberts asked him about his history with domestic abuse, and Brown stormed off the set and allegedly threw a chair through the window of his dressing room. Stylz remembers walking toward the room with Brown. “He was so upset,” he recalls. “Out of love, he said, ‘Flii, don’t walk with me. I want to hit shit. I want to swing at everything around me.’ I didn’t want to go in the room. He could have knocked anybody out.”

Just two weeks after his 2014 Billboard interview, Brown’s troubles returned: Suge Knight and two others were shot at Brown’s pre-MTV Video Music Awards party at 1OAK in Hollywood. This was just the latest in a series of violent incidents involving Brown and other prominent music figures, beginning with Rihanna in 2009 and including a brawl involving Drake’s and Brown’s entourages in June 2012 and a January 2013 incident in which, police said, he punched Frank Ocean. (Ocean did not press charges, but Ocean’s cousin -- who claimed that one of Brown’s guards injured him in the fight -- sued. Brown reportedly settled a year later for less than $20,000.) Though Brown didn’t appear to be directly involved in the 1OAK incident, Knight later sued both him and the club for not providing adequate security, calling Brown “a known gang associate with a history of violence” (the case is still unresolved).

By March of 2015, Brown had completed a 22-date tour with Trey Songz and rapper Tyga (although he was barred from entering Canada, the second of four places that would deny his visa based on past arrests in the United States). On March 4, Tran broke up with him when she learned that Brown had fathered a daughter, Royalty (then 9 months old) with the former model Nia Guzman. “One can only take so much,” Tran tweeted at the time. “No baby drama for me.”

It briefly seemed like meeting his daughter would overshadow losing Tran. “He didn’t see it coming,” says Stylz, “but Royalty changed his life. He’s a good dad. He really loves her, and he’s not faking that.” In April, Brown posted an Instagram picture of him cuddling her, captioned “God has blessed me with my twin,” and he named his next album, released that December, after her.

God has blessed me with my twin. #ROYALTY-- A post shared by @chrisbrownofficial on Apr 16, 2015 at 7:46pm PDT

Perhaps Brown saw an opportunity to make good in a way he had previously said his own father figure -- the man he has called his stepdad — hadn’t. Early in his career, Brown spoke openly about witnessing his mother’s physical abuse at the hands of Donnelle Hawkins. Hawkins later denied his stepson’s allegations, saying, “It is a way of not accepting responsibility for his own actions.” But Brown remembered that Hawkins “made me terrified all the time,” and said, “I don’t want to go through the same thing, or put a woman through the same thing that that person put my mom through.”

But he did. In June 2009, Brown pled guilty to felony assault for brutally attacking Rihanna while the couple were arguing in his rented Lamborghini after a pre-Grammy party that February. Longtime friends before they admitted to dating in 2008, Rihanna and Brown were the leading couple of R&B -- an image swiftly shattered when photos widely circulated of the gruesome facial injuries Brown had inflicted on Rihanna. The incident became one of the biggest news stories that year, with Brown excoriated in the press and Rihanna criticized too, when, in 2013, she and Brown for a short time rekindled their relationship.

Now, Brown is occasionally in contact with his biological father, Clinton Brown, who split with Joyce Hawkins when Chris was 6. Clinton, though, “isn’t happy with Chris,” according to someone who observed their relationship in recent years. “Look at the things he hears and sees. He’s not dumb.” During Brown and Rihanna’s reunion in 2013, Clinton told New York’s Daily News that he “personally really didn’t want him and Rihanna back together,” and compared his son to “Michael Jackson, Whitney Houston and Amy Winehouse.”

Brown’s relationship with his mother has shifted through the years. Hawkins co-managed Brown early in his career, a former member of Brown’s core team says, until her son asked her to step aside, and in November 2013, he threw a rock through her car window following a family session in rehab. “Nowadays, she’s not involved with [Brown’s] business anymore, and she keeps a distance from Chris,” says the former team member, though “when the baby came into play, they became much cooler.” Hawkins now “does everything” with Royalty. Brown -- who shares custody of Royalty with Guzman -- is “a great Instagram dad,” the source dismissively says. Hawkins, who declined comment through her publicist, remains a staunch supporter of her son on social media, regularly tweeting defenses of him in an exclamatory, all-caps fashion not unlike Brown’s own.

“I don’t think he hates women,” says one female former employee of Brown’s. “He’s actually a very sweet, sensitive guy. But they’re an easy target, and he’s a bully. It’s not just women -- it’s everyone, and he can get away with it.”

In the year following the spring of 2015, Brown slid deeper into the habits he had adamantly vowed to kick after leaving jail. Around April 2015, members of his team at the time say, he had broken a 15-month stretch of sobriety, going out on Xanax and lean. At a February 2016 Vanity Fair Italia shoot, a member of Brown’s team says he observed Brown snorting cocaine, which he was turning to more frequently. His moods became even more unpredictable. “We would ask, ‘What’s the temperature today?’ ” says a member of his security detail at the time. “You didn’t know how he was going to wake up. Were you going to get cool Chris? Or depressed or artsy and focused Chris, who would be very productive? Or the happy-go-lucky Chris, who would just joke around and have fun? It was a different person every day.”

On May 10, 2016, Brown was rehearsing his choreography for the One Hell of a Nite Tour at ShowBiz Studios in Van Nuys, Calif. As he would later detail in his lawsuit, Guirguis arrived at the studio at Brown’s behest, expecting to discuss the upcoming tour. A Coptic Christian of Egyptian descent who’s fond of posting Bible verses and inspirational phrases on his Instagram, Guirguis started his own management company, NiteVision, in 2008 and began working with Brown in 2012, reportedly to help clean up Brown’s image and get him off drugs. (Brown met Guirguis through his then-co-manager Abou “Bu” Thiam -- the singer Akon’s brother -- and subsequently hired Guirguis to manage him solo.)

“Let’s talk,” Brown immediately told Guirguis. According to the lawsuit, Brown, who was in a “(drug-fueled) rage,” led Guirguis to a private room down the hall, closed the door and said: “We are going to go for 30 seconds” -- fight, that is. Guirguis turned away to leave, but, the suit alleges, Brown smashed him in the face with his fist. As he fell backward, Brown punched him three more times in the face, jaw and neck. Guirguis was stunned. The two were very close; only a few weeks earlier, Guirguis had wished his “brother for life” a happy birthday on Twitter. He briskly left the studio and took an Uber to an emergency room. He quit that day. “Mike G was and is scared,” the suit reads, “not just for his own safety from Brown and Brown’s gang member friends, but also for the safety of others.”

Brown, according to a close creative collaborator at the time, “was ticked off” because Royalty had underperformed compared with his previous albums. (It’s his poorest-selling solo release, having moved just 366,000 copies in the United States.) “He sets himself up in situations where he can’t lose,” says another former core team member from that time. “Like, ‘I am so angry at myself, and I can beat up on [Guirguis] because I’m surrounded by people whom I pay to protect me. I can be the big man.’ And he can get away with it.”

“He’s basically the new Bobby Brown,” says a onetime member of Chris Brown’s management. “Think about how big [Bobby] was in the ’80s -- but you know he was a bad boy.” Another close past associate says, “He doesn’t know how to deal with the sins of his past. It’s always someone else’s fault. He becomes the victim. And I think he tries to numb whatever he is feeling.”

“It’s a tough transition to go from a teenager to a man and have the world at your fingertips,” says Dennis Ashley, the co-head of ICM Partners’ West Coast urban music division, who worked with Brown until 2010. Says Darden: “Many people who are thrust into the spotlight [as kids] are traumatized when they make a mistake and realize how fast that love turns to hatred. When I look in Chris’ eyes, I think that’s some of the pain.” Meanwhile, Brown, who recently posted an Instagram photo of himself standing amid a fleet of sports cars and motor bikes, “spends money before he has it, whether it’s cars, jewelry or drugs,” says a former Brown team member. “He has no appreciation of it. He never wants to hear he has no money, and he blames everyone [else] when his funds run low.”

By the time One Hell of a Nite launched in Europe on May 22, 2016, Brown lacked any kind of day-to-day management, according to a member of his security team at the time, and was lashing out at anyone who challenged his authority. That member of Brown’s personal detail recalls Brown screaming at his recently hired tour manager, Nancy Ghosh, threatening to beat her up because she asked his cousin not to smoke marijuana on the managers’ bus. She quit that day, May 23, sending an email, TMZ reported, in which she said that she felt unsafe because Brown had been acting “irrational and high on drugs.” (Ghosh declined to comment.)

“Once he did what he did to Mike G, there was no structure,” that former security team member says. “We had no manager telling us what to do or where we were going. He would make people sleep on the bus [instead of hotels] when he was mad at them. He was threatening people and cops. He was calling himself the devil.” By that June, Brown’s personal publicist of three years, BWR’s Nicole Perna, quit after a heated string of texts in which, TMZ reported, Brown accused her of not sufficiently promoting his new clothing line, Black Pyramid, and Perna replied, “Anna Wintour doesn’t want to f— with you. These editors don’t want to f— with you. The majority of my time is spent on damage control.” Brown had to fend for himself -- on social media, of course -- when, the next month, a landlord in Ibiza alleged that Brown and a group of friends had trashed a villa they were renting. Brown posted a series of videos showing a spotless house and calling out the landlord for “slandering my name.”

“Sober Chris is a solid guy with a big heart. High Chris and Chris coming off drugs is ungrateful, unappreciative and a foul person who most people don’t want to deal with,” says a close former associate. “Good Chris? You’ll fight for him. Unfortunately, the last couple of years, it has been drug Chris. That Chris is not a good dude.”

Lately, Brown seems to be locked in a holding pattern, his self-destructive tendencies offset by minor career successes. The single “Grass Ain’t Greener” charted on the Hot 100 last fall, but only after a chaotic August video shoot in which, according to a witness, Brown -- who was flown through a forest outside Fresno, Calif., in a harness while wearing gold teeth and a purple ponytail -- threatened a cameraman by saying his cousin would “knock his ass out,” then excused himself to the restroom where he was found two hours later, taking a nap.

In February, Brown posted a photo of Vanessa Vargas, a model with whom he had been romantically linked, on Instagram, apparently confirming their relationship even, says the former member of his personal detail, as he continued obsessing over Tran: “He’s always on social media, looking up who Karrueche was with, what she was looking like, what club she was at, who posted to her Instagram.” In her restraining order request, Tran wrote that in February 2017 Brown “threatened to kill me to others; threatened me via text messages; [and] threatened to harass my friends,” and that a few years ago, he had “punched me twice in the stomach” and “pushed me down stairs.”

“My biggest frustration is that we’re seeing someone who’s literally one of the most talented people in R&B and hip-hop, and he’s once again allegedly putting himself in a situation that makes it harder and harder for his music to be in the forefront of his brain,” says Darden. “I can be critical and talk about how Chris Brown needs to be a man, grow up and really take control of his life -- that’s easy for me to say. But some people need more than that, or a different kind of support.”

These days, former employees of Brown say, some of his closest friends are members of the Los Angeles Bloods. “He just doesn’t have the right people around him, people who are going to say, ‘Hey, dude, we shouldn’t be here,’ ” says one former management team member. “He lost Rihanna and Karrueche, two people he loved,” says Stylz. “Right now, he doesn’t trust anybody. I’m probably the one who loves him the most out of everybody who is not his real family, and he won’t even talk to me. I can’t get to him.”

In addition to the Party Tour, Brown has at least one other gig coming: a show at the Las Vegas club Drai’s, on March 18. Last summer, the club suspended Brown’s residency after he called its employees racist on Twitter, but now, management told TMZ, they “look forward” to Brown’s return. He is still signed to RCA Records and is represented by UTA, where he came on in late January 2016 -- and where Guirguis is in talks to join the music department. Brown employs Geragos, a well-known crisis attorney, and the veteran music attorney Kenny Meiselas. (RCA credits Meiselas and UTA with organizing the Party Tour.) But “he’s got no security, no management,” says the former security team member, who worked with Brown until recently. Several of Brown’s remaining business associates refused to speak to Billboard for this story, citing nondisclosure agreements or fear of Brown’s retaliation.

“You can talk to any drug addict or chemically imbalanced person -- it doesn’t just go away,” says a former member of Brown’s inner circle. “It’s something you have to work on. You have to change your lifestyle. And he’s not doing the things he needs to do to get well, so he’s never going to be well. The kid is going to hit rock bottom.”

The ultimate question may be just when he will hit bottom -- or so badly hurt himself or another person that the fragile balance between his personal life and career is upset. In the meantime, though, “there is always someone who wants to take care of Chris Brown,” says the former member of his personal detail. And “for some reason, Team Breezy fans are still strong and still behind him.”

“He does, believe it or not, have a kind heart, and he just wants to be loved,” says the former member of Brown’s inner circle. “At the same time, he’s incapable of being loved and loving.”

“My brother is going through a lot,” says Stylz. “But he’s not crazy. This isn’t why I invested all this time into him. He goes in and out of being angry, but we want to see Chris dancing and singing.”

This article originally appeared in the March 11 issue of Billboard.