Citizen Jay: How An Eccentric Racing Heir Became King of Hollywood Media

Jay Penske now controls ”Variety,” ”The Hollywood Reporter,” ”Rolling Stone” and some of the most esteemed cultural brands in publishing. And he’s just getting started

The car was designed to make an impression, low to the ground and coated in shiny black and gold, rolling out to a worldwide virtual audience last December to some tense electronic beats and stylishly frantic camera work. The debut of the newest all-electric Formula E race car from the DS Penske team was fittingly high-tech, with zooming close-ups of the dagger-shaped vehicle’s carbon fiber wings and fins, the big threaded tires. And painted in an elegant font around the cockpit was a familiar logo with a certain cultural cache: Rolling Stone.

On the nose was another famous name: Variety. And in back were more: Vibe, Billboard, Robb Report, Sportico and Variety twice again, with WWD painted at a smaller scale on both sides. The titles are notably literate in a racing world more accustomed to sponsors like Pennzoil, but here, they also represented the pride of ownership for team principal Jay Penske, whose day job is chairman and CEO of his ever-expanding namesake Penske Media Corporation.

The Los Angeles company is the owner of all those publications and more, from a near-monopoly of the Hollywood news trades to leading websites and magazines on art, music, TV, fashion, beauty, and real estate. PMC is also a producer of live events and, through subsidiary Penske Media Eldridge, is now an owner of the South by Southwest festivals of music, film, and technology in Austin, Texas. In January, Penske Media Eldridge announced the purchase of Dick Clark Productions and, with it, such legacy shows as the Golden Globes, the American Music Awards and the annual ratings juggernaut Dick Clark’s New Year’s Rockin’ Eve.

Penske, now 44, grew up in Detroit and New York around racing, as the youngest son of motorsports icon Roger Penske, the billionaire owner of the Indianapolis Motor Speedway, IndyCar and various championship-winning Penske Racing teams. Jay Penske has kept his hand in the family racing business by creating his own path, leaning into the future by going all-electric in 2014. So there he was, facing the camera a few months ago in a brief but rare public appearance during the team’s 15-minute online presentation, praising the new third-generation Formula E car, an open-wheel machine with a top speed of 200 mph.

“Our engineers, our mechanics, and everyone on our development team have worked tirelessly to get this car ready to race,” said Penske, handsome and fit in a team shirt covered with the logos of the same PMC brands. He praised the vehicle, a collaboration between Penske Autosports and DS Automobiles in France. Then he was gone.

Meanwhile, things are only getting busier at the office. For the last 14 years, Penske has carefully accumulated media brands at a time when the conventional wisdom—usually the worst kind—suggests that traditional print and online news media are in intractable decline. But Penske saw only opportunity amid a landscape of fading or undervalued titles, and he typically leads them to new financial viability where others have fallen short. As Penske builds this empire, it’s been a long time since he’s had time to sit with a book in the antiquarian bookshop he owned for years in the hills above Los Angeles. “He’s extremely, extremely busy,” says Variety COO Dea Lawrence. “He’s on planes, he’s flying, he’s a dealmaker, he works constantly. He’s the hardest-working person I know.”

“Anybody who’s putting money into fact-based journalism today is an angel,” says Stephen Galloway, former executive editor of the Hollywood Reporter and now dean of Chapman University’s Dodge College of Film & Media Arts. “He made an incredibly smart move in gobbling up as many trade outlets as possible that would effectively give him a monopoly on the business of entertainment news.”

It’s not just a business monopoly, but a cultural one.

Penske’s trajectory began with the 2009 purchase of Deadline, the trenchant online site covering Hollywood, from its founder, the notorious entertainment journalist Nikki Finke, remembered months after her death last year as both trailblazer and “terrorist.” (Finke told the world Penske paid $12 million for what was then a mostly one-person operation; the actual price was just below $1 million, according to one knowledgeable insider.) Then came Variety in 2012, Billboard and the Hollywood Reporter in 2020, along with a growing number of entertainment news sites like IndieWire. They are part of Penske’s ongoing accumulation throughout the past decade, from Women’s Wear Daily to, most recently, Artforum.

“He’s built a company, and he’s stuck with it,” says Richard Rushfield, founder of the online entertainment news upstart the Ankler. “He’s gone beyond the amount of time a mere dilettante would hang around.” But Rushfeld is wary of the concentration of titles Penske has amassed in entertainment. “Monopoly has never been good for any business, and for reporters in particular,” he warns.

Jay Penske during the Julius Baer Punta del Este Formula E race at Playa Brava Beach street circuit on December 19, 2015 in Punta Del Este, Uruguay.

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In the classic arc of fictional media titans, Penske appears to still be in the optimistic early years of Charles Foster Kane. From all accounts, he actively rejects the style of moguldom as perfected by his predecessors, the Murdochs and Bloombergs, who bludgeoned the public with their family brands and edifice-naming charitable largesse and actively sought to be kingmakers and, in doing so, become kings themselves (or, in case of Michael Bloomberg, mayor). Despite his ravenous acquisitions spree, Penske fashions himself as the anti-mogul. He scrupulously adheres to journalistic standards and seems to value his editorial staff. Some reporters at his titles still haul in major salaries—Kim Masters at the Hollywood Reporter is said to earn almost $400,000 a year. His ongoing accumulation of media follows a steady search of the marketplace for opportunities with struggling or undervalued brands. “We don’t go in as predators. We go in as nurturing new parents who recognize the importance of the brand we’re acquiring and how we can help bring it to the next step,” says Gerry Byrne, PMC’s vice-chairman.

While other publishers are retrenching, Penske is doubling down: Rolling Stone and Variety now employ more staffers than ever; in 2022, Variety notched the strongest revenues in its 117-year history. “When I started in the New York office, there were four or five reporters—now we have 15,” says Variety co-editor-in-chief Ramin Setoodeh. Shunning the spotlight, Penske makes a point of meeting with every employee at every new property, seeking ideas and input from the inside. “The thing about Jay is, he asks really tough questions,” says Setoodeh. “So you have to be prepared. You can’t bluff your way through a conversation with him.” Still, to most outsiders, he remains a handsome cypher.

Penske is rarely photographed on a red carpet, though he’s been seen inside exclusive events, like the annual Clive Davis pre-Grammy party at the Beverly Hilton Hotel, and at an Elton John performance at the Biden White House last fall. As publisher of the Hollywood trades and WWD, he’s certainly invited to every premiere and fashion show, can easily score entrée to the Oscars or Cannes, but you’re more likely to spot him from a distance at a Formula E racetrack. Working from L.A. instead of the publishing power corridors of Manhattan, Penske has already amassed more titles than Conde Nast’s Si Newhouse did in his prime, yet he is still no better known to most publishing insiders than he is to the public, who if aware of the Penske name at all, associates it with the family’s ubiquitous trucks with the distinctive PENSKE logo. (It’s notable that Jay Penske’s branch of the family business is identified through the discrete acronym PMC.)

Working from L.A. instead of the publishing hives of Manhattan, Penske has quietly amassed more titles than Conde Nast’s Si Newhouse owned in his prime.

Owning all these media outlets is coincidentally a good way for an especially private mogul to ensure that he doesn’t often appear in their pages. It’s a posture that seems unlikely to survive as Penske’s empire expands while stepping into music festivals (including last year’s LA3C in Los Angeles State Historic Park and Life is Beautiful in Las Vegas) and major television events through Dick Clark Productions. The owner of any one of these entities is by definition a public figure, and the expectations for the company’s namesake to explain himself will only increase. (Penske declined multiple invitations from Los Angeles to talk on the record.)

Most of Penske’s recent interviews are quick on-camera chats with Italian racing journalist Marcelo Padin, a Formula E enthusiast from Electric Motor News. They don’t talk about Hollywood. Penske is otherwise as private in the racing world as he is as a fast-rising leader in the media. “He’s one of the real enigmas still left in racing,” says British journalist Sam Smith, who covers international Formula E contests for The Race, and has only exchanged the occasional pleasantry with the team owner, but no interviews after nine years of trying.  “I don’t know if he revels in that image or not. Maybe he’s just a bit shy.”

Despite controlling most of Hollywood’s trade publications, Penske is seldom seen on the town, as in this rare night out with his wife Elaine Irwin and with Diane von Fürstenburg.

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For now, Penske speaks to the world mostly through press releases, but the few who have met with him at length typically describe him as good company, a smart guy with a plan, a mensch. But his silence leaves empty spaces for confusion and misinformation. Penske has been identified as a Trump supporter and major Republican contributor. He’s neither and, in fact, co-hosted what was supposed to be a Hillary Clinton victory party on Election Night 2016. More recently, he was pilloried in the literary world for closing down the beloved Bookforum magazine when he merely didn’t choose to buy it, while picking up sister publication Artforum.

It was also initially reported, even by some PMC publications, that Penske had accepted money from the same Public Investment Fund directly overseen by Saudi Crown Prince Mohammed bin Salman, which recently handed Jared Kushner’s investment firm a staggering $2 billion. PMC aggressively pushed back, noting the funds came from the Saudi Research Media Group, which has investments with Bloomberg and Hearst and is a public company audited by PricewaterhouseCoopers. And the money came two years before the murder of dissident journalist Jamal Khashoggi which turned the Saudi prince into a pariah. Regardless, some remain uncomfortable with the Saudi connection. “At a time when others would not take it, he lined up to take it, and it’s fueled a lot of this growth,” notes one knowledgeable media insider. 

As on Succession, empires seem to run in the family. Penske’s father, Roger, retired as a race car driver while still in his 20s to begin his larger career in the 1960s, which grew from car dealerships to truck leasing, now with revenues of $32 billion. At 86, and with no plans to retire, the Penske patriarch only recently laid out a succession plan with his two older sons–Greg and Roger Jr.–positioned to take the lead, while Jay, the youngest, charted a personal path on several fronts. Both father and son have stated that Roger provided no funding for PMC, which presently has about 1,800 employees.

Penske’s parents met in a Colorado ski shop. His mother, Kathy, was an English teacher. Jay played high school hockey and lacrosse and was a voracious reader, given to quoting philosophers in casual conversation. He showed flashes of rebellion—he was kicked out of an exclusive prep school for misbehavior—and was disinclined to follow his elder siblings into the family business, starting instead a short-lived automotive title, one of his few publishing failures. In his 20s, he dated actresses Gina Gershon and Lara Flynn Boyle, who nicknamed him “Jaybird.” His early days in L.A. media were greeted with skepticism, and he was brutally dismissed by Gawker (“The Hard-Partying Si Newhouse Wannabe of Bel Air”).

Racing icon and founder of the $32 billion family trucking empire, Roger Penske did not, with his youngest son’s approval, underwrite Jay’s media ventures.

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In 2012, he married supermodel Elaine Erwin and fully settled into Los Angeles as a family man and a captain of industry, but he’s not publicly active in local politics. He endorsed no one in last year’s mayoral contest, though he’s known Rick Caruso for years. In 2019, his father was awarded the Presidential Medal of Freedom at the White House by Donald Trump, drawing a group of family members into the Oval Office. Standing in the back, Jay inevitably stood out, looking like Bruce Wayne or a movie producer in a dark blue suit.

After graduating in 2001 from the Wharton School of the University of Pennsylvania, Penske landed in the Bay Area for his first successful venture, as cofounder of Firefly Mobile, which made cell phones for kids. He then relaunched and sold the successful email portal and headed south to Los Angeles to buy Finke’s Deadline Hollywood Daily, a crucial first step in building Penske Media. He personally recruited the top editors, poaching Variety’s veteran film reporter Mike Fleming to become Deadline co-editor-in-chief with Hollywood Reporter TV writer Nellie Andreeva.

“Like everybody, I had a complicated relationship with Nikki, but she was great at what she did,” Fleming says of the difficult decision to jump ship after 20 years at Variety, where he’d been hired by Peter Bart. “Jay has lived up 100 percent to everything he said to me, kept his word and then some.”

As the new media company began to grow, Penske invested time and money in Dragon Books, a lovingly furnished antiquarian bookstore located next to a Starbucks near the corner of Beverly Glen and Mulholland Drive. Penske would often work from there anytime he wasn’t in the Deadline office. He attended classes at rare book schools, met with book dealers in Los Angeles and at book fairs, and developed friendships with several authors, including historian A. Scott Berg. (One neighborhood customer, Kiss co-founder Gene Simmons, bought a first edition of The Lord of the Rings for his son, Nick.) Penske kept Dragon Books going for 17 years until PMC grew too large and his daughter was born.

With the help of a loan from Daniel S. Loeb’s hedge fund, Third Point, Penske made his first shocking move: buying Variety in 2012 for about $25 million, less than half of the $60 million paid when it previously sold in 1987. He started with changes in the executive offices, recruiting Michelle Sobrino, Variety’s first female publisher, and veteran entertainment journalist Claudia Eller as co-editor-in-chief. Penske ended the online paywall for most content and killed the foundering Daily Variety in 2013 but surprised many by upgrading the weekly print edition into a glossy magazine that survives a decade later. Many of these changes had been in discussion for years, but it was Penske who finally pulled the trigger, upending the stasis he mocked as “NATO”–or “no action, talk only.”

The acquisitions of Deadline and Variety were only the beginning. In a move that sparked antitrust concerns from the Department of Justice, PMC signed a $225 million deal in 2020 to acquire 80 percent of Media Rights Capital, the parent company of the Hollywood Reporter and Billboard. The Reporter’s editor-in-chief, Janice Min, had earlier made a splash by transforming the tired trade into a glossy lifestyle title and later embarked on a similar revamp at Billboard. But according to one insider, both publications had been losing more than $20 million every year for more than a decade prior to PMC buying them. After PMC took control, there were meaningful cuts to the lavish photography and feature-writing budgets and layoffs of non-editorial employees.

The PMC headquarters in West Los Angeles.

With PMC’s addition of the Hollywood Reporter, the two historic Hollywood trades were owned by the same entity for the first time. Unlike other media consolidations, there was no advantage to consolidating or finding “synergies” because maintaining the status quo is essential, as studios buy lucrative “For Your Consideration” ads in all of the trades rather than just one. And even as the awards shows themselves have lost audience share, the FYC ad campaigns target a much smaller constituency. Which means the Oscars could regress all the way back to a nice dinner at the Cocoanut Grove, and it wouldn’t affect ad sales.

“It’s conceivable that as the awards become nothing but an inside vanity game that these granular little trade publications may be the last thing standing because they make economic sense,” says a journalist at one of the PMC trades. Another industry source complains, “[Penske’s] got Variety, Deadline, Hollywood Reporter, and IndieWire all doing the same story, written by different people. That is only a real business if the FYC market is justifying it. And it has.” Counters Variety’s Setoodeh, “It’s as competitive as it’s ever been. And if that means getting a scoop on a story from [the Hollywood Reporter], it’s all hands on deck. My staff doesn’t want to lose that story to anyone, even if it’s another brand in the building.”

The competition for entertainment news remains intense. If anything, there are only more outlets, reflecting an insatiable appetite far beyond an industry readership. Like Deadline beginning in 2006, and TheWrap a few years after that, a new generation of online upstarts is taking on the trades, led by the Ankler and Puck. Any one of them might break a big story that takes all the oxygen out of a particular Hollywood news day. “The trade mentality is a vortex,” adds the PMC journalist. “It’s imposed on itself by all of the people who work there. A certain kind of person goes into that, where they have to win every minute. Everything’s a crisis. When they lose, they don’t distinguish much between important, not important.”

This year, PMC stepped aggressively into television with the purchase of Dick Clark Productions, the company founded by the late host of American Bandstand and TV’s Bloopers & Practical Jokes. From his ivy-covered headquarters in Burbank, Clark, who died in 2012, built a lasting television empire that includes the American Music Awards, Academy of Country Music Awards, and the Golden Globes. The deal comes just as traditional awards shows are losing audience share (though the Oscars were up for the second straight year with nearly 20 million viewers in 2023).

Jennifer Coolidge celebrates at the Golden Globes, now owned by PMC through its acquisition of Dick Clark Productions.

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In 2016, Dick Clark Productions was valued at $1 billion but is now in rebuilding mode as awards show contracts with various networks expire. Two weeks after Penske’s purchase, the company laid off 15 percent of its staff, according to Deadline. PMC is looking to follow the 30-year example of Billboard’s Latin Music Week, a conference and several days of live music in Miami built around the Billboard Latin Music Awards, according to one insider. Similar events centered on its awards brands for country music and the Globes seem inevitable.

Buying Rolling Stone was another turning point for Penske and PMC, bringing into the fold a title with deep history and lasting influence, with a general readership deep­ly engaged with pop culture and politics, hip-hop, Hollywood and rock and roll. Over the years, Penske has told friends and colleagues about an uncle up in Portland, a lifelong music lover and musician, who used to send him cassettes of classic rock. His uncle once urged the youngest Penske that if he wanted to be cool, he had to read Rolling Stone.

When Penske approached owner Wenner Media, it was in precarious financial health in part from selling a 50 percent share of Us magazine and then buying it back from Disney, adding new debt to the company. There was also a devastating loss in a defamation lawsuit over a 9,000-word Rolling Stone investigative article about a gang rape at the University of Virginia that turned out to be false. At first, the magazine’s founder, Jann Wenner, sold 49 percent of the company to BandLab Technologies, a Singaporean company, which left him in control of his magazines, but he ultimately chose to sell the remainder. There were many suitors for that 51 percent stake, said to include music industry titan Irving Azoff. Equally surprising was who didn’t bid–Conde Nast and Hearst, experienced publishers of general interest magazines–suggesting the uncertain position Rolling Stone was in by the end of 2017. The winning bid went to PMC. Penske ultimately purchased the remaining 49 percent of ownership in 2019. When the deal with Wenner Media closed, Penske told friends, he called his uncle and sang to him “The Cover of ‘Rolling Stone,” the hit by Dr. Hook & the Medicine Show. The magazine was his.

In his 2022 memoir, Like a Rolling Stone, Wenner described the new owner as “a good-looking young man with a terrible haircut. . . . I was impressed with his energy, ambition, and smarts.” But he was alarmed by changes in the new era: “Jay took direct control of the editorial budget and enjoyed cutting costs. . . . many of our good writers were forced out. The new mantra was clear: What counted was not the power of the printed word but the number of ‘hits’ on the website.” Wenner was notoriously slow to embrace the web and, for several years, even licensed to RealNetworks. Penske hired a new top editor for the magazine and website, Noah Shachtman, who spent seven years leading the hard-charging Daily Beast, who emphasized the magazine’s political reporting, drawing new eyeballs to the site. Wenner’s son, Gus, remains as Rolling Stone’s CEO.

Penske’s interest in general readership publications has continued with PMC’s $100 million investment in February in Vox Media, in a deal that, true to the Penske playbook, valued Vox at half of what it was just seven years earlier. Vox already runs New York, its flagship magazine, with multiple sub-brands (Vulture, Intelligencer, the Cut) that enjoy large, engaged readerships. New York has a history as celebrated as Rolling Stone’s but, in the last year, Vox has seen falling ad revenue and the furlough of 7 percent of its staff. At a time when many legacy media brands are teetering financially, Penske has apparently figured some things out in the digital age. “We’re learning from each other,” says Vox Media CEO Jim Bankoff. “I’m certainly impressed with how he is able to both run quality publications and a quality business that respects the product, respects the employees, and respects the business partners.”

Team Penske’s flagship Formula E race car sports the logos of Variety, Billboard, and other PMC titles.

Penske Autosport

Part of that involves Penske personally meeting with every employee at a newly acquired business for 30 minutes each. He held about 200 meetings just with the staff of SXSW, says Byrne. “Jay makes it a point to sit down with every person who is part of the enterprise that’s coming into the Penske Media operation–from the editor-in-chief to the publisher to the person who’s cleaning the floors at night,” says Byrne.

Not every act of kindness has been appreciated. One Thanksgiving, Penske bought a spread from the Beverly Hills Hotel and personally delivered the meal to Finke, a notorious shut-in. Hours later, she called, enraged that chocolate cake was included since she was diabetic. “She said I was trying to kill her,” Penske told the New York Times. A day or two later, Finke posted on Deadline: “Jay Penske is the worst CEO in history.” Penske allowed the post to remain on the site he now owned, and today has a printout of the words framed in his office. Finke and Penske continued working together for another three years. Their relationship was a peculiar mix of professional and personal, employer and problem child. When she died last year in hospice, Penske was one of only two people who turned up to pay their respects.

In late October 2012, Hurricane Sandy landed hard on Long Island. Deadline editor Fleming’s father stepped outside at the wrong moment, hit his head on the stoop, and was one of 11 people who perished in the storm. Penske heard about the tragedy and headed east. “Jay flew in from California and found a car,” Fleming recalls. “There were trees all over the road. And he came to my house. I was shocked.” Fleming had never experienced that level of concern from an employer or had ever heard of such a thing. As the editor says now, “Who does that?”

At the racetrack, things are always clear, win or lose. Penske picks up an ePrix trophy in India one weekend, then finishes second in the next contest in Cape Town. After racing for a few years with IndyCar, he was among the first to secure a franchise when the Formula E championship began in 2014. He seems committed, even if electric racing has generated the same skepticism he’s faced from publishers convinced that investing in legacy publications with storied brands but uncertain business models is a sucker’s play. Now that even the Dodge Challenger muscle car is phasing out internal combustion engines after next year, it’s clear which argument is winning in automobiles. Penske’s strategy in publishing is vulnerable to pitfalls known and yet to be revealed, but so far, he appears to be on the right track.

“I don’t know how to run a newspaper,” Orson Wells, as Charles Foster Kane, confessed eight decades ago in Citizen Kane. “I just try everything I can think of.”

If Jay Penske were talking, he just might agree.

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