The Weeknd on the Crew That Boosted Him From ‘Basically Homeless’ to the Super Bowl

What are you talking about?” asks the man in the pinstriped suit. “About me?”

The conversation in question is, in fact, about a nearby Los Angeles recording studio. But much as the sun will rise in the east and set in the west and all roads lead to Rome, so too do all discussions among this group ultimately return to the man in the pinstripes. “Hi,” he says, reaching for a handshake. “I’m Abel.”

Abel is Abel Tesfaye, a quiet charmer who makes small talk about his holiday plans, remembers my name and apologizes when, just once, he interrupts while I’m talking. Abel Tesfaye is also, of course, The Weeknd — the sometimes-brooding, always-intriguing, silk-voiced underground R&B golden child turned pop prince.

In the suit, a fur-collared overcoat and diamond stud earrings for today’s photo shoot, he certainly looks the part — albeit one very different from the role he’s played with the dedication of a method actor over the past year. In music videos, late-night appearances and awards show performances for his blockbuster album After Hours, Tesfaye appeared with a mangled face and wore a blood red jacket — a charismatic sociopath inhabiting an eerie horror movie world equal parts Halloween and Fear and Loathing in Las Vegas.

Tesfaye, 30, didn’t create it alone. He was joined every step of the way by the three equally sharp-dressed men chatting with him now on the patio of a Hollywood Hills mansion. Together, they are the brain trust of XO Records, the four co-founders of the label that has been synonymous with The Weeknd since he blew up out of Toronto in the early 2010s with a dark, relentlessly carnal strain of electronic-laced R&B.

The compact, gregarious man in the gray plaid is their de facto leader: Wassim “Sal” Slaiby, 41, The Weeknd’s manager and founder/CEO of management company SALXCO. Partnered with parent company Live Nation, SALXCO oversees a roster of roughly 20 artists (including French Montana, Doja Cat, Bebe Rexha, Ty Dolla $ign and M.I.A.) and about the same number of heavyweight producers. Some of the latter, like Metro Boomin and London on Da Track, work with a wide network of artists in hip-hop and beyond (including, often, SALXCO’s own); the rest, like Illangelo and DaHeala, essentially function as an in-house production team for The Weeknd.

The stylish, precise man in the black three-piece is La Mar C. Taylor, 30, XO creative director, founder of the Toronto youth talent incubator HXOUSE and companion to Tesfaye since they met in high school economics class half a lifetime ago. The quiet man in the navy is Amir “Cash” Esmailian, 37, the teddy bear of the group; he co-manages The Weeknd with Slaiby, runs his own management company, YCFU, and carries two cellphones — each with a different service provider, so he never misses a work call.

In a year when a pandemic brought much of the industry to a halt, these four men — all immigrants or sons of immigrants to Canada — not only pushed forward, but thrived. Their decision to stick to After Hours’ March release kicked off a year in which the album and its omnipresent lead single, “Blinding Lights,” dominated the charts while Tesfaye dominated virtual performances with his unwavering cinematic vision. And as the music business confronted a historic reckoning with racial justice, the diversity that has always powered SALXCO and XO — among their staff, constellation of artists and the Starboy at its center — set an example other companies are scrambling to emulate.

“Our artist Ali Gatie is Iraqi. M.I.A. is Sri Lankan, Nav is Indian, Abel is Ethiopian, Belly is Palestinian, I’m Lebanese,” says Slaiby. “Cash is Persian. La Mar is Jamaican. [SALXCO executive vp] Lindsay Unwin is Canadian. You’ve got the United Nations over here. That’s how it’s been for almost 20 years.”

They may look like the ultimate industry insiders now, but Tesfaye, Slaiby, Esmailian and Taylor succeeded in 2020 for the same reason they have since first convening 10 years ago as scrappy Toronto upstarts: Their tight, familial bond is the foundation for their success, not the other way around. They’ve counseled Tesfaye out of a bad early management deal and through his crossover to the pop mainstream. They’ve guided him to statement-making career highs, like his upcoming halftime performance at the Super Bowl on Feb. 7 — a “Rubik’s cube of problems,” as Taylor puts it, that took six months of Zoom calls and email chains to sort out. They talk every day, play basketball twice a week and spend holidays together.

And when the going gets tough — as it did when The Weeknd received no 2021 Grammy nominations despite the commercial and critical success of After Hours — they band together, hunker down and push forward. “I know deep down in my heart that everyone would have been successful in their own realm if we’d never met,” says Tesfaye, nodding at his friends. “But us together — [what we’ve created] wouldn’t have happened without every single one of us in this room. All of the decisions I make, I don’t make without these three people here.”

***

Sal Slaiby knows how to make an entrance. He arrives in a tank-size SUV with his wife, Rima Fakih Slaiby — 2010’s Miss USA and the mother of his three young children. (They met at a pajama party at Diddy’s house.)

An excitable guy who wears jewelry that looks to be worth even more than his ride, Slaiby has a gift for negotiation — “There’s stuff where it’s like, ‘No way you’re going to get that,’ and then he gets it,” says Esmailian — and is fiercely protective of his artists and employees. “I’m good under pressure,” he says matter-of-factly. “I’m the guy you call if you have a problem. You don’t need to call me if everything is great today.” He breaks into his signature high-pitched laugh. “But if a fire is going on, ring my phone.”

Born in Ghazir, Lebanon, during the civil war of the 1970s and ’80s, Slaiby spent much of his early life in a bomb shelter. He fled to Montreal, then Ottawa alone at 16 and spoke little English when he arrived. There, he met a neighborhood kid named Ahmad Balshe — a Palestinian-Canadian rapper who’d eventually become XO artist Belly — who introduced him to Esmailian, whose own family had emigrated from Tehran amid the Iranian Revolution.

By the early 2000s, the three had gone into business together, as Slaiby and Balshe co-founded hip-hop/R&B label Capital Prophet Records (Esmailian headed street promotions, then became an artist manager). Three-hundred miles west, in Toronto, Tesfaye and Taylor had their own hustle going. Raised by single mothers in the city’s Scarborough suburb, they were, as Tesfaye puts it today, “basically homeless” high school dropouts posting his music to YouTube and Facebook — without his face on it. “We just kind of played into that mystery for a year or so,” says Taylor, “until we got to the point where we couldn’t hide his face anymore, because he was just that famous.”

In 2010, Esmailian was living in Miami, working to break Belly in the city’s hip-hop scene. But when a friend sent him a few tracks by an up-and-coming Toronto artist who called himself The Weeknd, he dropped everything and booked a flight home to Canada for the next day. “This kid is ahead of his time,” Esmailian remembers thinking. “I knew it right away.”

In the first of what would become many nights on the town together, Esmailian and Tesfaye hit a Toronto club with some mutual friends the very evening Esmailian landed. The pair were fast friends, and with The Weeknd’s debut mixtape, House of Balloons, about to blow up, Esmailian became “the manager, the road manager, security and the driver.” By late 2011, Tesfaye had put out two more mixtapes, and the hype around him had escalated accordingly. Hanging at Balshe’s apartment one night around this time, he and Esmailian met Balshe’s neighbor, Slaiby. “La Mar and Abel were going through a hard time,” says Slaiby. “They had a different team that screwed over their businesses. The songs were flying. Their career was flying. But their business was in a danger zone because they didn’t have the right team.”

“We surrounded ourselves with people who thought they knew everything and almost literally ruined our chances,” explains Tesfaye. Slaiby’s more pragmatic approach — “You get what I’m good at, and I tell you where to go for everything I’m not good at,” he says — appealed, and he and Esmailian extricated Tesfaye from his bad deal. They became The Weeknd’s co-managers, and shortly thereafter, the four men founded XO.

Early on, they figured out that taking chances — and operating on their own timeline — often made sense. The Weeknd’s “whole mysterious aesthetic,” as Taylor puts it, meant his music had to speak for itself. “I think that’s really what captivated everyone and catapulted Abel into the stratosphere,” Taylor continues. That buzz soon translated into big potential paychecks, but the XO crew didn’t jump at them: When an Australian promoter offered a $160,000 gig, they passed on it and others like it, opting instead to play clubs around Canada. “I knew how important it was to build the touring business,” says Esmailian. “At that point, we could have gone to step four or five, but I knew we had to start at step one. We were doing 500-person venues, but there were 2,000 people outside trying to get in.”

When major labels inevitably started circling, that groundswell became leverage. Among those interested were Republic Records co-founders and brothers Monte and Avery Lipman. “They came to Toronto, like, 10 times,” says Esmailian. “These guys are not running a small company — and going to Toronto, you’ve got to deal with customs — but they just kept showing up.”

“When you come across someone as gifted as Abel, you do everything and anything to hitch your wagon to their success,” says Monte Lipman, “because you know this kind of artist has an opportunity to change the world.” But the Lipmans weren’t solely compelled by his music; Monte calls the XO team “as competitive as anyone I’ve ever worked with,” praising “their expectations, loyalty and wolf pack mentality.”

Republic’s tenacity resonated with The Weeknd’s team, as did the fact that the Lipmans ran a family business. “You feel that in the company,” says Slaiby. “Everyone cares.” In the fall of 2012, XO entered a distribution and strategic partnership with Republic and its parent company, Universal Music Group. “Even just getting music on iTunes and Apple Music, we weren’t fully familiar with that, and they were,” says Esmailian. “Same with radio. They provided the structure.” The deal gave XO independence and Tesfaye ownership of his masters — now a clause Slaiby insists on for any artist contract. “If you’re 70 and want to retire, selling 50% might be a good deal,” he says. “But I definitely vote to own your own shit all day.”

Within six months, Republic’s muscle had paid dividends: Without a radio hit, The Weeknd was headlining venues like London’s 20,000-seat O2 Arena. His team wondered how much more massive these shows could be if he was actually on top 40 radio; still, Tesfaye was cautious. “I didn’t even know if I wanted to cross over at that time,” he says. “A lot of artists that succeed in the underground world, they’re scared to take that leap. I felt that way.”

But after disappointing sales of his 2013 debut studio album, Kiss Land, Tesfaye realized he wanted more — and Republic provided him the perfect boost into the pop mainstream. “Love Me Harder,” a duet with labelmate Ariana Grande, became his first hit on the Billboard Hot 100, peaking at No. 7. (It wasn’t just corporate synergy either: In October, they reunited on her album positions.) Five months later, Republic made his “Earned It” the linchpin of its Fifty Shades of Grey soundtrack — and a No. 3 solo hit.

“To me, ‘Earned It’ is the best crossover song I could’ve ever had,” says Tesfaye, “because it feels like a Weeknd record, but it also feels like it’s transcending. It felt fresh and it felt new and it felt pop.” He’d found a mainstream niche without abandoning his sound, one which defined his subsequent albums, 2015’s Beauty Behind the Madness and 2016’s Starboy. Both went to No. 1 and had tours averaging $1.1 million a night — quite a difference from the days when, Esmailian recalls, “we’d finish a tour and be down $200,000.”

“In the beginning, we went for broke,” says Taylor. “Abel put all of his money back into the production.”

“He has never been driven by money,” adds Esmailian.“I didn’t know what having money really felt like,” admits Tesfaye. “I don’t know what it feels like to lose money if I never had it. Even to this day with the label, it’s like, ‘Guys, I will put my own money into this music video. It’s happening.’ ”

Around that time, Tesfaye became one of only 13 artists to ever replace themselves at No. 1 on the Hot 100 (when “The Hills” overtook “Can’t Feel My Face”) and the guys — who had been living at the SLS Hotel in Beverly Hills for the better part of a year — officially moved to Los Angeles.

Here, they could finally enjoy the trappings of success: money, sports cars and mansions — Tesfaye’s in the Kardashian-strewn enclave of Hidden Hills, his three buddies just down the 101 in Encino and Echo Park. But they weren’t quite ready to kick back by their pools. “Honestly,” says Taylor, “with every project it feels like we’re just getting started.”

***

On Nov. 25, 2019, Tesfaye got behind the wheel of a Mercedes-Benz electric SUV, and the world heard snippets of The Weeknd’s “Blinding Lights” for the first time.

The commercial in which he appeared was, like most decisions, the result of brainstorming with Slaiby and the XO team. “I like brands that are heritage, legacy,” says Taylor, who often meditates and hits the gym before working on performance and video concepts, design and, yes, brand alignments. “I like household names that hold weight in conversation, because that’s how I hold XO.” After a bidding war between several major brands eager to debut the single, Mercedes, says Slaiby, “was our bazooka.”

It was the last time Tesfaye would appear in public as himself for some time. “Blinding Lights” came out the next day, with a video introducing the man in the red jacket — who’d spend the year swaggering through five more videos, plus late-night and awards-show performances, his face morphing through bruises, bandages and an unsettling (fake) plastic surgery. “That takes a lot of bandwidth and determination,” says Taylor, “to stay true to a singular vision for 365 days.”

It’s not out of character for Tesfaye though. Over the course of four studio albums, he has always seemed more interested in building a consistent sonic world than drastically reinventing himself from project to project. But Tesfaye admits that’s not always his natural inclination. “They call me ‘Diapers’ because I always change my mind,” he says, eliciting a laugh from his cohorts. “La Mar keeps me on track, for example, with music videos and keeping a [consistent] body of visual work. I have a knack to be like, ‘I want to do something else. I want to look different. I want to drop more music.’ They’re there to be like, ‘Let’s just keep this focused.’ ”

Tesfaye appeared on Saturday Night Live on March 7, 2020, 13 days before the planned After Hours release. It ended up being the show’s last live taping before pandemic lockdown. Other stars soon began delaying anticipated albums, and the Republic/XO teams agonized over the best course of action. The final decision came down to Tesfaye. “Abel was like, ‘You know what? F–k it,’ ” says Taylor. “ ‘We’re going to double down. We’re going to put it out, and whatever comes of it comes.’ ”

The Weeknd’s new music, it turned out, was oddly well-suited to the strange early days of quarantine, a time when the real world, much like that of After Hours, felt dark and often surreal. A week after its release, Dua Lipa’s Future Nostalgia arrived — another pandemic album strongly influenced by ’80s dancefloor sounds, though of a more purely euphoric variety. After Hours offered a different kind of escapism: tunes for when your grip on reality was starting to slip, or for grasping at some joy amid the dystopia of 2020.

“One of my favorite moments was during the middle of the pandemic, seeing kids on TikTok dancing to ‘Blinding Lights,’ ” says Esmailian. “Just having fun with the people in their house and their families.”

“And the hospitals too,” adds Tesfaye, “and the nurses.”“The album was therapeutic for a lot of people,” says Taylor.

“To be honest,” says Slaiby, “it was therapeutic for us.”

After Hours spent four weeks at No. 1 on the Billboard 200 and collected nearly 900 million on-demand U.S. streams in 2020, according to MRC Data. “Blinding Lights” spent a record 43 weeks in the top 10, and The Weeknd topped a slew of Billboard year-end charts, including Top Hot 100 Artist, Pop Songs Artist and R&B Albums Artist. Critics loved the album. So did those dancing nurses. You may have loved it, too.

Most might assume, then, that when Tesfaye woke up in his L.A. penthouse on Nov. 24, the day would have gone roughly as he had imagined. But when the 2021 Grammy nominees were announced, a seemingly auspicious day turned into a situation the XO team now calls “shocking ” (Taylor), “disrespectful” (Slaiby), “nightmarish” (Esmailian) and, as Tesfaye himself puts it, “an attack.”

***

They were the 80 characters heard round the world. “The Grammys remain corrupt,” Tesfaye tweeted shortly after nominations were announced — with none for him or After Hours, an album of the year favorite. “You owe me, my fans and the industry transparency.”

“I use a sucker punch as an analogy,” Tesfaye says today. “Because it just kind of hit me out of nowhere. I definitely felt … I felt things. I don’t know if it was sadness or anger. I think it was just confusion. I just wanted answers. Like, ‘What happened?’ We did everything right, I think. I’m not a cocky person. I’m not arrogant. People told me I was going to get nominated. The world told me. Like, ‘This is it; this is your year.’ We were all very confused.”

As Tesfaye fielded messages from “people I haven’t spoken to in ages, the entire music community, all my peers,” Slaiby called interim Recording Academy president Harvey Mason Jr. “I wasn’t mad,” says Slaiby, whose use of the F-word increases significantly as he talks about the Grammys. “I was a gentleman. I said ‘Hey, bro, how are you? How’s your day? Our day is shit. What the f–k just went down?’ ”

Mason expressed his own surprise and asked Slaiby what he’d do if their roles were reversed. “I’m the CEO of a company,” says Slaiby. “I understand things go wrong. I said that I’d call a 911 staff meeting and figure out what the f–k happened and then call me back so we can figure out how to handle this, because the whole world is talking about it.”

Industry speculation hovered around a few theories — one being that Tesfaye might have incurred academy wrath for planning to perform at both the Grammys and, a week later, the Super Bowl. Mason quickly dispelled that, telling Billboard that “at no time would we be upset if he were to perform on the Super Bowl.” (The Grammys have since been postponed to March 14.) And anyway, as the XO team sees it, their artist shouldn’t have incited any bad blood.

“Historically Abel has ‘played the game,’ so to speak,” says Taylor. “He’s rubbed those shoulders; he’s done those performances; he’s talked to those high-level people. We’re very well respected. A lot of people know us, individually and as a collective.” Tesfaye, like plenty of other industry onlookers, wondered if something else entirely was at play.

“If you were like, ‘Do you think the Grammys are racist?’ I think the only real answer is that in the last 61 years of the Grammys, only 10 Black artists have won album of the year,” he says. “I don’t want to make this about me. That’s just a fact.”

The Weeknd’s music had been submitted in six categories: three general field awards (record, song and album of the year); one pop; and two R&B, the latter of which were moved to pop by a genre screening committee (which exist across genres to oversee a first round of properly categorizing potential nominees). After a first round of voting open to all academy members, nomination review committees — which each comprise 15 to 30 voting members whose identities aren’t disclosed — narrow down top-vote getters to those on the Grammy ballot. Many categories, including pop, are not overseen by those committees, but the Big Four are.

“What is that secret committee? What the f–k?” Slaiby demands. The only way, as he sees it, to right what happened is “they cancel the f–king secret committee and become full transparency. It’s a powerful, special award,” he continues, “but the leadership there has got to go. They’re weak.” (The Recording Academy declined to comment further for this story.)

“Look, I personally don’t care anymore,” says Tesfaye, sounding 90% at peace and 10% like maybe he still cares a little bit. “I have three Grammys, which mean nothing to me now, obviously. It’s not like, ‘Oh, I want the Grammy!’ It’s just that this happened, and I’m down to get in front of the fire, as long as it never happens again.

“I suck at giving speeches anyways,” he adds. “Forget awards shows.”

That’s actually not quite true. As his incendiary tweet proved, Tesfaye has found power in brevity when it comes to using his platform to speak out, particularly in the past year. When he won the award for best R&B at the MTV Video Music Awards in August, he accepted with a succinct statement: “It’s really hard for me to celebrate right now and enjoy this moment, so I’m just going to say justice for Jacob Blake and justice for Breonna Taylor. Thank you.” In the wake of George Floyd’s murder, he donated $200,000 to Colin Kaepernick’s Know Your Rights Camp Legal Defense Initiative, $200,000 to the Black Lives Matter Global Network and $100,000 to National Bail Out. The day after, he posted the logos of Spotify, Apple Music, Sony Music, Warner Music and UMG to Instagram, writing that “no one profits off of Black music more than the labels and streaming services” and challenging them to “go big” with their own donations.

At the Super Bowl, he’ll have a unique opportunity to show how much he can make of a moment. Last year’s halftime show, headlined by Jennifer Lopez and Shakira, drew 102 million viewers. The Weeknd’s performance will be the second curated by JAY-Z’s Roc Nation. That makes him the first Black artist to anchor halftime since the company entered its partnership with the NFL in 2019 — a move widely perceived as an attempt to transcend backlash to the league’s treatment of Kaepernick and the other largely Black players protesting racial injustice.

“We always had the Super Bowl on our bucket list, and we’ve always had timelines for all of our goals,” says Esmailian. “It came a few years earlier than we expected.” To capitalize on the event’s vast audience, XO and Republic curated a just-released 18-track highlights album. And though the game will happen in a stadium only about a third full, the XO team is well prepared. “We’ve been really focusing on dialing in on the fans at home and making performances a cinematic experience, and we want to do that with the Super Bowl,” says Tesfaye. Slaiby adds that, though the organizers are as usual covering all production costs, Tesfaye put up $7 million of his own money to “make this halftime show be what he envisioned.”

Once it’s over, he’ll have to figure out what role, and what universe, he wants to inhabit next. Public health permitting, he’ll set out on a 2021 summer/fall tour that has already nearly sold out six dates and is on track, Billboard estimates, to average $1.2 million to $1.4 million per show. “Is the tour going to be the After Hours tour still? Is it going to be this new album’s tour, with the same tickets?” Tesfaye wonders aloud. A year from now, he says, the man in the red jacket won’t be around — though maybe he’ll make an appearance for a few songs on tour. “It’s a whole puzzle I’m trying to wrap my head around right now.”

No doubt, Slaiby, Esmailian and Taylor will be beside him to help him put the pieces together. “Those guys were my groomsmen for my wedding,” says Slaiby. “Those are my brothers — my everything.” When our conversation ends, all four pile into that giant SUV, carpool to his place and order in sushi. Like a regular family, but with nicer suits.

Correction: A previous version of this story incorrectly stated that The Weeknd’s Super Bowl halftime performance would be 24 minutes long. As in previous years, it will be roughly 12-13 minutes long.  

This story originally appeared in the Jan. 30, 2021, issue of Billboard.