The Curious Rise of Twitter Power Broker Yashar Ali

In just a few years, he’s become one of the most fearsome media figures in the country—mobilizing his vast Twitter following to promote his famous friends and punish foes. Can his own past survive similar scrutiny?
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I’m extremely upset.”

Yashar Ali delivers this news as he settles into a booth in the lobby of Santa Monica’s Proper Hotel. His eyes are red and puffy—he’s clearly been crying—and his voice cracks with emotion when he speaks. Something terrible has happened, the death of a beloved friend, and Ali can’t help but spill his grief into my tape recorder as we start our interview. “He was just so resilient,” he says, sighing deeply.

The deceased, it turns out, is an orphaned elephant named Luggard, who, before he succumbed to a deadly infection, lived in a wildlife refuge in Kenya that Ali has been raising money for through his extremely influential Twitter account. “You can get people to care about animals if you help them realize that they’re just like us,” he says.

To his 800,000 Twitter followers, Ali’s aching sentimentality won’t come as a complete surprise. They know that this 41-year-old scourge of the internet—the political-operative-turned-social-media-muckraker who took down Sharon Osbourne, hobbled the cabinet chances of L.A. mayor Eric Garcetti, canceled food writer Alison Roman, and helped crush Harvey Weinstein—is actually a big softy. At least when it comes to elephants. And orangutans. But when it comes to everybody else who ends up in his Twitter account’s sights—A-list celebrities, media bosses, and politicians (especially the ones he’s become intertwined with personally and financially)—he’s a force to be reckoned with, emerging over the last five years as one of the most feared and powerful voices on the web.

Part investigative journalist, part gossip columnist, and part trusted confidante, Ali is a uniquely twenty-first-century media personality—an openly gay Iranian American convert to Catholicism who claims he attends Mass three times a week. He sends out an average of 60 tweets a day—a manic jumble of jokes, news bites, and gossipy commentary about politics, media, aviation safety, the royal family, Scientology, gay heartthrobs, wildlife preservation, and bath linens.

But his more barbed tweets have also made serious headlines, helping to topple not one but two Fox News anchors—Kimberly Guilfoyle and Eric Bolling (the latter was fired after Ali reported that he was sending dick pics to a colleague). His Twitter bombshells during the Mueller investigation made even Jared Kushner sweat. He’s so well-connected, he could reveal what former president George W. Bush really thought about Donald Trump’s inaugural speech (“That was some weird shit”). Such scoops have brought him serious cred: In 2019, he joined former president Donald Trump, Cardi B, and Alexandria Ocasio-Cortez on Time magazine’s list of the most influential people on the internet. Last year, he was invited by Twitter CEO Jack Dorsey himself to give suggestions to Twitter’s C-suite on how to improve the platform.

Though he’s a contributor to New York magazine and Huff Post, his byline shows up infrequently. Instead, he breaks his biggest stories on Twitter and in his Substack newsletter, unencumbered by the fact-checking and legal vetting required by many news organizations. And while some of his methods may seem suspect to traditionalists, he has nonetheless won the admiration of the biggest stars in the media business. I asked him to suggest a few acquaintances who might comment about him, and he replied by sending a spreadsheet listing the personal emails and cellphone numbers of more than 40 bold-face names, including actresses Busy Philipps, Mandy Moore, and Kristin Davis, along with Piers Morgan, Axios’s Mike Allen, Politico’s Sam Stein, talk show hosts Meghan McCain and Abby Huntsman, and Irena Briganti, the much-feared head of communications at Fox News.

CNN president Jeff Zucker, No. 6 on Ali’s list, is usually a difficult guy to reach but he quickly jumped on the phone to talk about his friend. “Yashar has this incredible Twitter feed with several personalities within it,” he said. “He’s not just an investigative reporter, he’s not just an animal lover, he’s not just a bon vivant and a man about town—he’s all of those things, and that’s actually what makes him so interesting.”

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Ali is a fixture on MSNBC news shows.

MSNBC.com

When we finally meet, the exuberant Renaissance man described by Zucker and others is only partly in evidence. In person, he is funny, self-deprecating, and disarmingly intimate—full of generous compliments and world-class dish. During our chat, he texts with a former high-level Obama aide, then deftly deconstructs the online-bullying scandal that has enveloped his BFF Chrissy Teigen—No. 30 on his list. He loves suspense, gossip, and high-stakes intrigue. But the combination of the pandemic and the sudden death of Luggard has taken a toll. He’s emotional. On several occasions, when discussing his relationship with his family, he breaks down in tears.

Today, a dusty-skied afternoon in May, he’s dressed in an oversized gray T-shirt, blue sweatpants, and the same San Francisco 49ers cap he sports in his youthful Twitter profile photo, which looks like it might have been snapped for his high school yearbook. (He swears that it was taken just before the pandemic.) Still, he looks about as doleful as a one-eyed dog in an ASPCA ad. He may be on a first-name basis with a platoon of A-list stars, but at the moment Ali’s feeling underappreciated. “I’m a caretaker for many people,” he says, taking a sip of his water. “Something that frustrates me is that people don’t take care of people like me.”

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It’s a strange comment, coming from him. In fact, a full accounting of Ali’s impressive ascent over the past two decades—his humble beginnings as a Hollywood production assistant; his transformation into a powerful political aide to then-San Francisco mayor Gavin Newsom; his tangled relationships with a slew of celebrities; his stunning reinvention as a social media star—are a testament to his uncanny ability to get lots of very important people to care for him. Interviews with former colleagues, friends, and fellow reporters paint a portrait of a highly intelligent and empathetic operator who, despite his knack for exposing the indiscretions of others, has managed to obscure a rather checkered history of his own.

On Twitter, Ali often shares very intimate, often moving details about his family, his friends, and his constantly shifting state of mind. But for a journalist who puts so much of his private life into the public sphere, he is secretive and resistant to scrutiny. Several years ago, when he transitioned out of working in politics, he stopped going by his birth name and switched to Ali, a move he says he made to protect his family. He rarely consents to interviews and ignored several requests before consenting to meet with me, two times over three months. There are very few photos of him on the internet, and he darkens his silhouette during online appearances. He required that all of his on-the-record quotes be pre-approved and firmly rejected a photo shoot, claiming he didn’t want to be recognized by Scientologists. But the church isn’t the only one on his trail. While reporting this story I was contacted by a well-known private investigator, who was digging into Ali’s past on behalf of another client.

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Ali (far left) with then-San Francisco mayor Gavin Newsom and his wife, Jennnifer Siebel, in 2009. Despite a thin political portfolio, Ali parlayed fundraising for Hillary Clinton into a job as Newsom’s chief of staff.

DAVID PAUL MORRIS/GETTY IMAGES

“There’s a little bit of the Talented Mr. Ripley in him,” says a former colleague. Though he has insinuated in public and in various profiles that he’s the scion of a wealthy Iranian family, public records show that he’s encountered a slew of financial hardships in recent years. He’s been evicted from multiple residences, defaulted on several loans, and has racked up tens of thousands of dollars in tax liens. He seems to have no fixed address, preferring to live in the homes of generous friends. (He’s currently installed in the West Hollywood house of an entertainment-industry power broker.) But sometimes he overstays his welcome. He’s been sued by a member of the Getty family over a financial dispute and fallen out with several other powerful members of San Francisco’s and Los Angeles’s entertainment and political elite.

“He’s always attached himself to rich, powerful people and to elected officials and made himself appear indispensable,” recalls a former colleague who worked alongside Ali in Newsom’s San Francisco office. Like many people interviewed for this article, he declined to speak for attribution out of concern that Ali might somehow retaliate. “I don’t exactly fear him, but he can be vengeful and very vindictive.”

How Ali acquired so many powerful supporters is a bit of a mystery. Even his closest allies are a bit fuzzy about how they met. “I don’t remember how we became friends,” says New York Times Washington correspondent Maggie Haberman. Zucker has a hard time recalling, too. “That’s a really good question. How do I know Yashar?” So does CNN anchor Jake Tapper. “I couldn’t tell you how we met, but suddenly he was a presence in my life—a wonderful one,” he says. “It just feels like he’s always been in my life. But I don’t know that I’ve ever met him in person.”

According to Ruby Cramer, a writer for Politico who has been a close friend of Ali’s since 2012, “Yashar has a way of immediately becoming close to people, but not as a strategic tactic. You immediately become a part of his world and he becomes a part of yours. People have questions about Yashar because he doesn’t fit into your concept of what a reporter or a political operative looks like. There’s something mysterious about him that people have tried to diagnose—but those questions miss the point.”

Ali grew up in Oak Park, an upper-middle-class Chicago suburb. His father, who emigrated from Iran in the mid-’60s, is a respected professor of mathematics at the University of Illinois at Chicago; his mother worked in the school’s public health department. He attended Oak Park High School for a year before transferring to Holy Cross, subsequently converting from Shi‘ite Islam to Catholicism. He has written extensively about being bullied over his Iranian heritage and says that he didn’t have a single friend until he turned 15. He’s revealed that relations with his family have been strained due to his sexual orientation and that he didn’t speak with his older sister for years. He says he suffers from crippling ADHD and bouts of depression, which have afflicted his life and his finances.

Hoping to break into television, Ali skipped college after graduating from high school and moved to L.A. He found work as a production assistant on ER and Chicago Hope before pivoting to politics in 2002, first as a volunteer for Kevin Feldman’s unsuccessful run to unseat California Congressman Henry Waxman and then on Steve Westly’s gubernatorial campaign. After reading an article about Iranian-born businessman Hassan Nemazee, Ali reached out, and the two struck up a friendship. In 2010, Nemazee pleaded guilty to bank fraud and was sentenced to 12 years in prison, but not before he introduced Ali to Clintonworld fixture Terry McAuliffe. The former DNC chair recruited Ali for Hillary Clinton’s 2008 presidential campaign, and he wound up organizing a series of successful fundraisers, including an event at the Hollywood home of director Roland Emmerich that raised $200,000.

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Democratic donor Susie Tompkins Buell (left) guaranteed a loan for Ali and let him crash in her penthouse.

JUSTIN SULLIVAN/GETTY IMAGES

Ali’s political career really took off when he decamped from L.A. to San Francisco in 2008. His Clinton connections helped him land a staff job on Newsom’s first gubernatorial campaign in 2008. Newsom, then mayor of San Francisco, made an early exit from the race, but before that Ali was able to secure an endorsement from Bill Clinton. That coup led to his appointment in 2009 as Newsom’s deputy chief of staff. Within Newsom’s inner circle, Ali’s scant political experience raised questions. “Yashar didn’t even have a goddamn resumé,” says one former aide, who recalled the team struggling to create a press bio for the new hire due to his conspicuous lack of experience. Many believed he had access to a vast family fortune, a perception that Ali seemed to encourage. “My parents have worked very hard,” he told an SF Gate reporter. “They’ve been very nice to their son.”

Former colleagues from that era remember him as a moody and sometimes impulsive presence who zealously guarded his privileged perch within the City Hall hierarchy. “He left a bad taste in a lot of people’s mouths,” one source said. He wielded total control over Newsom’s social media channels and was reluctant to share any of the passwords. Drama seemed to follow him around. Four of Ali’s former coworkers from that time remember him bringing a gun to the offices of SCN Strategies, a powerful political consulting firm, setting off a minor panic. (Ali claims he just brought along an ammunition magazine—not a gun—to display while he was working on a gun-safety ballot initiative.)

Over time, Ali became less concerned with City Hall minutiae than with building his relationships with the Bay Area’s power elite. His job with Newsom brought him into frequent contact with the city’s wealthy and well-connected donors—none more impressive than Susie Tompkins Buell. The billionaire cofounder of apparel brands Esprit and The North Face is one of the Democratic Party’s top donors. She’s given tens of millions to support the presidential campaigns of Bill Clinton, Al Gore, John Kerry, and her close friend Hillary Clinton. Ali and Buell first met at a political dinner around 2008 and soon became friendly, trading small talk at political events and gossip over drinks. As their relationship deepened, he advised her on art purchases, helped her recoup a valuable book that had been stolen, and organized an auction of her furniture. Ali started referring to Buell as his “godmother” and she grew fond of the young man, telling friends how sensitive and gentle he could be. Eventually, he moved into one of her houses in Bolinas, occasionally crashing at her penthouse in Pacific Heights.

By then, Ali had also befriended heiress Ariadne Getty, a member of the San Francisco-based oil dynasty that has backed Newsom throughout his political career. Ali and the heiress, an extremely private person who in recent years has been a major donor to LGBTQ causes, became close through Ali’s work for Newsom, and soon he was flying in regularly from San Francisco to visit Getty at her $14 million condo at the Beverly Hills Montage. But sources say their relationship began to sour after Ali began borrowing large sums of money from her in 2012. In a civil complaint she filed against Ali in 2017, Getty claims the loans eventually totaled $179,000. The former friends reached an agreement under which Ali promised to pay the heiress back in monthly installments. He made only two of those payments before defaulting, according to court documents. The debt is still outstanding.

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Heiress Ariadne Getty (left) sued Ali to recover $179,000 she loaned him; and Ali lived rent-free at Kathy Griffin’s Bel-Air mansion for nine months. “Kathy, you’ve got a grifter,” warned an acquaintance.

AURORA ROSE/PATRICK MCMULLAN VIA GETTY IMAGES | GARY MILLER/FILMMAGIC

Starting around 2013, members of Buell’s inner circle also began growing suspicious of her ever-present new friend. Ali persuaded Buell to auction off a world-class collection of midcentury photographs, bringing in a seven-figure sum and pocketing a hefty commission for himself. Soon after, a source says, he began urging Buell to unload additional collections, with the implicit understanding that he’d earn a fee for his assistance.

He sat in on financial meetings with Buell’s accountant and family members, too, to the discomfort of some who attended. In 2016, while working on Newsom’s first gubernatorial run, Ali tangled with top Newsom strategists and fled his office, never to return, leaving behind a large cache of Buell’s sensitive financial documents. Though the items were mailed back to Buell, the family was furious about the breach. Two years later, following some other financial disputes, Ali’s relationship with Buell completely fell apart. Reached for comment, Buell would say only, “I cared about Yashar until I couldn’t anymore because he was doing things that were unacceptable. He did a lot of good things for me, but he doesn’t understand boundaries. It’s painful to think about.” She hasn’t spoken to Ali in over a year.

By then, Ali had found a new friend. In the spring of 2017, comedian Kathy Griffin’s life was quickly unraveling following a photo shoot in which she posed holding a prop resembling Donald Trump’s decapitated head. Death threats poured in by the thousands. Griffin was promptly fired from her gig at CNN, venues canceled her upcoming comedy tour, and lucrative endorsement deals disappeared overnight. The Secret Service launched an investigation. Griffin was as radioactive as a celebrity could get. Desperate, she turned to an unlikely savior—one of her favorite Twitter personalities who’d often been complimentary about her on the platform.

She DM’ed Ali, and as fate would have it, they discovered a weird connection: they’d both attended the same high school in Chicago, and Ali recalled attending a party at her house in L.A. years later. Initially, they discussed simply doing an interview to clear up the Trump matter. But as their relationship grew closer, Ali morphed into Griffin’s unofficial advisor and shadow publicist. He introduced Griffin to sympathetic journalists, schooled her in the intricacies of social media, and strategized about which publications and late-night talk shows would best serve her career rehabilitation. Eventually, Ali took an even more active role in her comeback, writing a glowing profile of Griffin for New York. When Ali said he was coming to L.A. in the spring of 2018, Griffin invited him to stay at her 13,000-square-foot Bel-Air mansion. According to a source close to Griffin, he ended up living there for nine months. (Ali insists he stayed less than six.)

Playing a similar role for Griffin that he’d played for Newsom and Buell, Ali became the comic’s confidante-slash-executive assistant, though he was never on Griffin’s payroll. He took an active role in managing Griffin’s social media accounts, helped her set up a merchandise company, and came to her defense in a property dispute by posting an embarrassing audio clip of a wealthy neighbor screaming expletives. He made a brief cameo in a Keeping Up With the Kardashians Christmas special, which he attended as Griffin’s guest. He did Griffin’s grocery shopping and cooking, jobs that usually fell to Griffin’s paid staff. In exchange, she let him live in her home rent-free and lent him one of her cars. But as the months wore on, Ali became increasingly reclusive, holing up in his bedroom and rarely leaving the house. Staff members assumed he was busy writing, but people around Griffin grew concerned when he started receiving official government mail at her home address.

One evening in the fall of 2018, Griffin invited journalist Joan Walsh, the national affairs correspondent for The Nation and a former political analyst for CNN and MSNBC, to join her for dinner. After Ali made an appearance, Walsh began probing Griffin about the nature of her relationship with him. Walsh says she got the sense that Griffin wanted Ali to leave but was too intimidated to force the issue. “I completely believed that she was uncomfortable and maybe even afraid, and I sympathized with her,” says Walsh. After listening to Griffin’s story and seeing her evident anxiety, Walsh told her host, “Kathy, you got yourself a grifter. You have to get him out of here.”

It would take several more months, but Griffin finally asked Ali to leave in early 2019, enlisting two part-time male assistants to help oversee the packing of his belongings. Then they ordered him an Uber and sent him on his way. (Ali says he only stayed with Griffin at her urging, and left of his own volition. He says the comedian even threw him a going-away party when he moved out.) Griffin declined to speak about Ali on the record. However, a representative for the comedian offered a statement on her behalf: “Sometimes you make a new friend and that friend turns out to be quite a different person than you thought they were.”

Asked about this trail of tarnished relationships, Ali says that NDAs he has signed with Getty, Griffin, and Buell limit his ability to respond to their version of events. “I have grappled a lot with entering into codependent relationships of all sorts over the past decade,” he explains in an email. “Wanting to fix things and wanting to fix too much was one of my dysfunctional behaviors. It’s something I’ve talked about in therapy at length and something that I’ve worked past but it . . . still makes me sad when I think about it.”

Even as Ali was dealing with all these personal travails, he was carefully constructing his own media brand, building an exalted perch in the tangled hierarchies of Twitter, and amassing an audience that included some of the most recognizable names in entertainment and media. Gradually, he became one of the most effective users on the platform, deploying his account not merely to make famous friends but to promote his political ideas, castigate his enemies, and, of course, break news. He’s been front and center in the ongoing culture wars amplified by Donald Trump’s presidency and the #MeToo and Black Lives Matter movements. And he’s used his social media muscle to help expose some of the most infamous malefactors of our times. Harvey Weinstein? Ali landed an early scoop from accuser Lauren Sivan. Les Moonves? Ali reported that the disgraced former CEO and chairman of CBS harbored a nasty vendetta against Janet Jackson. At Fox News, he broke embarrassing scoops about several hosts, including Bolling and Guilfoyle. Weinstein now sits in prison in upstate New York while Moonves and Bolling were fired and promptly exiled from public life. Ali, meanwhile, has been busily collecting accolades: he made National Journal’s 2020 NJ50 list, which honors those who are “changing the game in Washington.”

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Latimes.com

But last October, Ali was more focused on local politics, training his sights on L.A. mayor Eric Garcetti. In a Substack post, Ali accused Garcetti’s longtime aid Rick Jacobs of inappropriately kissing him on the lips at dinner parties and embracing him for uncomfortable periods of time. He also accused Garcetti of condoning the behavior. The mayor, an early Biden supporter and a member of his vice-presidential vetting team, was reportedly on the short list for several cabinet jobs, including leading the Department of Transportation. It’s widely acknowledged within political circles that Ali’s series of blog posts accusing Jacobs of sexual misconduct helped foil Garcetti’s chances of landing a cabinet position. While Garcetti is now being considered for an ambassadorship in India, Ali’s crusade against him has continued. On Tuesday he Tweeted that his lawyers had sent a letter to the City Attorney’s Office demanding the release of several deposition transcripts related to a sexual harassment lawsuit against Jacobs filed by a former LAPD officer who was once part of the mayor’s security detail.

Of course, not all of Ali’s postings—some 200,000 tweets in total—are journalistic in nature. He has also detailed his experiences as a gay Catholic Iranian American, ruminated on ear-lavage procedures, and even written eloquently on the menstrual cycles of Orcas. “I’m vulnerable on Twitter, and that creates trust,” he says. “I share things that I care about personally, and I also share the stuff that people would consider to be messy. Somebody I’ve never met tweeted at me the other day, ‘We refer to you by your first name in our household.’ As in, ‘Today Yashar said this, and today Yashar said that.’ Whatever that is, reporters don’t have that. I don’t know any reporters who have that, which is fine. I’m unusual.”

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When he’s not working as a journalist, Ali finds time to raise funds for a wide array of worthy causes. In addition to elephant conservation, he’s mounted drives for the rehabilitation of Black churches. Previously, he’d worked in partnership with two nonprofits—Robin Hood in New York City and Tipping Point in San Francisco—to raise more than $1 million for COVID victims. To do this, he used the donation site GoFundMe, which has built-in transparency tools. So eyebrows were raised last March when Ali announced his latest COVID-relief crowdfunding effort, which involved simply retweeting requests for funds from needy Twitter followers or offering to collect money himself and parcel it out. “If you want to give to the folks who lost their jobs and are replying with their @CashApp or @Venmo, but don’t want the hassle of figuring out who to give money to, you can send me the money and I will distribute 100% of it in a transparent fashion,” Ali tweeted on March 22, 2020.

According to experts in philanthropy, soliciting charitable funds from a private Venmo account raises red flags. The FBI has a warning on its website urging people against wiring money to Venmo and CashApp, calling it “a favorite scammer tactic.” An IRS spokesman told Los Angeles that using a peer-to-peer payment app like Venmo to solicit charitable donations was a “bit of a gray area for us—it’s certainly not something we would encourage.”

To be sure, there’s no evidence that Ali has done anything illegal with the funds. Indeed, Venmo, which has an explicit policy discouraging freelance fundraising, raised Ali’s spending limit in support of his effort. He does seem to be doling out at least some of the money he collected, though how much he has raised and how much has been distributed is unclear. Ali says he raised around $7,000 to his Venmo account and gave it all away in $100 and $200 gifts. He claims he donated $150,000 of his own money during the pandemic to people in need.

Ali’s own struggles with the pandemic were abundantly evident last April, when we met for the first time, at the Four Seasons in Beverly Hills. He claimed I was only the second person he’d seen since L.A.’s lockdowns began and, though he had been vaccinated, was skittish about being in public. He said he’s been contending with several health issues and rarely leaves his house other than to see his therapist. He spends most of his day tweeting and talking to sources.

Taking stock of Ali’s journalistic accomplishments is tricky. Many of his major scoops have held up, including one—the news that Jared Kushner was a “significant person of interest” in the Russia investigation—that was served up simply as a tweet reply. And the range of topics on which he’s had an impact is impressive. In a recent profile of Endeavor CEO Ari Emanuel in The New Yorker, Connie Bruck cited previous reporting by Ali. He chalks up his successes to a mix of hard work, hyper focus, and crack research skills that he sharpened as a political operative.

And yet, to many, there’s also something unsettling about his journalistic approach. In focusing on the overlapping worlds of media, politics, and the entertainment industry—where the stakes are extremely high and personal grudges abound—he relies heavily on anonymous sources, sometimes by the dozens. For example, in June 2020, Ali published a story about Barbara Fedida, a veteran ABC News executive, alleging that she had made racist comments to her staff, provoked dozens of HR complaints, and cost ABC millions of dollars in confidential settlements. His story relied on comments from 34 sources—none of them on the record. Five days after Ali’s post appeared, ABC fired Fedida, after an internal investigation confirmed that she’d made “racially insensitive comments.” But the network knocked down most of Ali’s other assertions, denying that she had provoked any legal actions or HR complaints.

Some of the charges in Ali’s story had been floating around for awhile; other news outlets had sniffed around the accusations after being approached by an agent representing an ex-CBS employee who’d recently been fired by Fedida. None of these other outlets bit, however. “We didn’t feel comfortable going with someone who had an obvious ax to grind,” says one media reporter who looked into the allegations but passed on the story. What makes the fact that Ali did bite so curious is that Fedida had been a friend of Ali’s—they texted frequently and dined together—as well as a news source. But then that appears to be something of an ongoing pattern with Ali.

Before he published the story that upended Rick Jacobs’s life, they too had been on good terms. Over the course of a friendship dating back to 2005, Ali had attended at least a half dozen events hosted by Jacobs at his home. According to several sources present at these parties, the kisses had seemed like a long-running gag between the two men, so they were shocked when Ali framed them as sexual harassment. But nobody was more surprised than Jacobs, who thought of himself as a mentor to Ali and often counseled him on his career.

Which is not to say that Ali turns on all his friends. Sometimes he can be ferociously loyal. Take, for example, Leah Remini (No. 5 on Ali’s list). Ali and the King of Queens-actress-turned-activist have been close for years—she’s the one who inspired his anti-Scientology crusade. When she was fired from her yearlong stint at The Talk in 2011, Remini publicly blamed cohost Sharon Osbourne of orchestrating her departure. She’d later retract the accusation (telling Howard Stern the reason she got fired was that “I am not good at interviewing celebrities”) but then retracted her retraction last April, when Osbourne found herself in hot water for defending controversial comments by Piers Morgan (No. 43 on Ali’s list). The outlet where Remini resurfaced her allegation? Ali’s Substack, where she was the only on-the-record source in a brutal post—citing 11 other anonymous sources—accusing Osbourne of a long list of offenses, including bullying and using racist language. Days later, Osbourne was fired after more than a decade on the show.

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Ali has been a guest on CBS’s The Talk, with Sharon Osbourne (left) and Julie Chen.

LIZZY SULLIVAN/GETTY IMAGES

In defending his friends—not to mention going after his enemies—Ali can be unflinching, even in the face of high-powered Hollywood publicists. While he was reporting the Osbourne story, he received a text from Howard Bragman, a well-known crisis PR agent who was representing the embattled talk-show host at the time. Bragman offered to explain Osbourne’s side of the story off-the-record, and to provide Ali with documents and emails that supported her version of events. “Try to control your enthusiasm,” he urged the reporter. “There are two sides to every story.” But Ali wasn’t interested. “I don’t do well with lectures or scolding, my friend,” he replied to Bragman. “I’m not some regular entertainment reporter. I’m Iranian and focus on investigations… I don’t need anything from anyone and throw cease-and-desist letters in the shredder… I am not scared of anyone and no one can do anything to me.” He added, somewhat surprisingly, that he has a “long-standing policy” against using off-the-record sources.

That righteous moxie propels a lot of Ali’s reporting. But it also makes many of his pieces highly reductive—most have clearly identifiable villains and victims and a crusading hero in the person of Ali himself. While no one can doubt he’s helped expose serious malfeasance, the public fallout that often results from his crusades has at times been hurtful and troublingly lacking in nuance. Once, when he was talking about the impact of his stories, I asked him if he ever felt any remorse about attacking people who once considered him a friend. “Never,” he said. “It doesn’t bring me down because I’ve been getting results. If I wasn’t getting results, it might. There’s no story I’ve ever done where it was a one-time mistake.”

It’s probably not a coincidence that Ali has amassed his power and influence just as traditional journalism outlets have been suffering through a death spiral. Between 2008 and 2019, newsroom employment has dropped by more than 23 percent. The bleeding out of the industry has led to new levels of desperation. Every day Ali is inundated with pleas from journalists to retweet their stories, which can result in significant traffic boosts. A top editor at Insider (formerly known as Business Insider) recently circulated an internal memo urging staffers to seek out retweets from Ali to optimize the impact of their stories. The fact is, like it or not, Ali’s feed is impossible to ignore, and traditional newsrooms are struggling to keep up. After Ali published his Rick Jacobs piece, the L.A. Times dispatched a team of reporters to pursue the story and ran a string of follow-ups. Ten years ago, it was a link on the Drudge Report that prompted newsroom backslapping. Now it’s a retweet from @Yashar.

“[Ali’s ascent] says something good about the media—that it can still be a meritocracy, and if you’re smart and resourceful and industrious enough and you righteously stand up for the causes you believe in, and if you break a lot of stories, you can rise,” says Tapper. Asked about Ali’s financial problems and the Getty lawsuit, the CNN anchor seems surprised but holds his ground. “He’s out there doing what journalists are supposed to do—providing comfort to the afflicted and afflicting the comfortable.”

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New York Times food writer Alison Roman (right) parted ways with the paper after Ali posted unflattering remarks she’d made about his friend Chrissy Teigen (far left).

MTV AWARDS: CHRISTOPHER POLK/MTV1415/GETTY IMAGES; ALISON ROMAN: CLINT SPAULDING/GETTY IMAGES

But at a time when reporters are losing jobs over college tweets or even the appearances of conflict, Ali’s own history and tangled connections rarely receive much scrutiny. Take his reporting on Alison Roman, formerly a star food writer and personality for the New York Times. In May, Roman gave an interview in which she criticized design guru Marie Kondo as well as Ali’s good friend Chrissy Teigen. The interview, which appeared in an obscure newsletter, may well have gone unnoticed had Ali not taken a screenshot of it. Roman’s remarks—while clumsy—took aim at excessive consumerism and celebrity branding, but many thought they smacked of racism. The Times promptly suspended the food columnist, who issued an abject apology. Unconvinced of her sincerity, Ali then resurfaced an old Halloween photo of Roman in what he deemed a “chola” outfit, accusing her of cultural insensitivity. Roman explained she was actually dressed up as Amy Winehouse, but the Times reported on the incident anyway. Roman left the paper in December and, according to a source close to her, remains furious with Ali and her former employer.

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A few weeks ago, Ali’s Twitter feed took a decidedly darker turn. Just days before this story went to press, and in the midst of fact-checking, he shared on Twitter that he was suffering from suicidal ideations. “Going to bed hoping to not wake up,” he wrote. His revelations about his suicidal thoughts continued for well over a week, prompting concern and warm words of support from thousands of people, including his eclectic mix of bold-faced friends. Everyone from Rabbi Wolpe, the famed rabbi of Temple Sinai, to atheist Sam Harris offered words of encouragement. An array of public figures from Megyn Kelly (“You are too important to too many ppl”) to Valerie Jarrett to Sarah Silverman (“We got you”) to Mark Duplass (“Value the shit out of you”) chimed in. Even Trump lawyer Jenna Ellis expressed concern. (“Love you, Friend”). It was more proof, though he sometimes can’t see it, that people care for Yashar Ali.

Back at the Four Seasons, as I turn off my recorder and get up to leave, Ali is in an upbeat mood, eager to share. (I later discovered he had been secretly recording me, as well.) He tells me he’d be happy to sit and chat for several more hours, but it’s getting late. I affix my mask and we exchange pleasantries, bump fists, and make plans to talk again. It’s now dusk, and the snarled traffic on Doheny is an unwelcome sign that the world—after a truly horrific year—is finally getting back to normal.

As I exit the driveway, I steal a glance over my shoulder and notice that Ali is still seated at our table, alone, avidly scrolling through his phone.


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