Let’s Play Penskopoly!

A little over a decade after wading into the Hollywood trades, automotive heir Jay Penske has mastered the art of buying distressed media properties and dominating once-thriving niches such as entertainment, music, fashion, and now (he hopes) fine arts.

Illustration by Steven Dressler

When news broke last month that Penske Media Corporation was buying Artforum, it seemed like Jay Penske, the 44-year-old media mogul son of a trucking billionaire, who’s already conquered trades covering film, music, and fashion had locked up yet another culture industry’s trade color group in the style of the Monopoly board game. Following his purchase of Art in America and Artnews in 2018, the acquisition of Artforum completed a trifecta of American legacy art publications covering the broad scope of the commercial art world.

It follows Penske’s domination of other industry trades: After buying Deadline from its founder Nikki Finke in 2009, Penske has gone on to scoop up the two biggest Hollywood trades, Variety in 2012 and The Hollywood Reporter in 2020, as well as smaller rivals including IndieWire and awards site Gold Derby, founded as a blog by Hollywood journalist Tom O’Neil. (Hollywood Life, a site that Penske started in 2009 with former Us Weekly editor Bonnie Fuller, has been solely owned by Fuller since 2021.) “Penske is a very big name in the film world and the film critic world because of the publications that fall under its purview,” said Devika Girish, co-deputy editor of Film Comment, a nonprofit independent publication supported by Film at Lincoln Center, and a critic contributing to The New York Times among others.

Penske’s operated similarly in other industries, if with less absolute domination than the entertainment industry trades. Penske moved into the music category in 2017 when he purchased a majority stake in Rolling Stone from founder Jann Wenner and then full ownership in 2019, a move that eventually resulted in the elevation of fellow nepo baby Gus Wenner to be the magazine’s CEO. In the 2020 deal for The Hollywood Reporter to Penske’s holdings, he added the leading music industry trade Billboard and Vibe magazine, a consumer title focused on hip hop and R&B. Penske became a major player in the fashion trades in one fell swoop when he acquired Fairchild Fashion Media from Condé Nast in 2014 including titles like Women’s Wear Daily and Footwear News. Then, in 2018, Penske added She Media, which operates fashion site StyleCaster as part of its portfolio of women-focused titles.

Penske has edged into related live events, as well. In 2021, PMC swooped in to buy a 50 percent stake in the music, film, and media confab SXSW after the pandemic crippled its finances. Last year, the firm added the Las Vegas music festival Life Is Beautiful, started by the late Zappos founder Tony Hsieh, under the Rolling Stone umbrella and The American Pavillion, a corporate sponsor event space at the Cannes Film Festival. Elsewhere, the Fairchild brand survives primarily as a live event series.

Even some of Penske’s earliest media acquisitions seem to follow the same consolidation curve. After acquiring gadget blog Boy Genius Report in 2010, Penske has added other media outlets that tell rich people which toys to buy: Penske launched an affiliate commerce site in 2016 and bought into the leading rich-people toy magazine Robb Report in 2017. (The latter of which has given lavish coverage to one of Penske’s non-media holdings, a 707-acre private island in the Bahamas that his company currently marketsas Torch Cay, which Robb Report gushed, shortly after Penske bought it, is “the only private island in the world where you can land your ultra-long-range and heavy private jets.” So convenient!)

Alas, one sector that does not appear to be on Penske’s radar is the publishing world: As part of his deal to buy Artforum, its Bookforum spin-off was shut down. A Penske representative did not respond to requests for comment for this story.

The consolidation Penske has managed so far has given him a Charles Foster Kane-like presence in the sectors he cornered. Film Comment’s Girish couldn’t remember a time in her career when Penske didn’t dominate film industry news. “It’s where the film community gets industry news, production news, it’s the websites and the publications we use to stay abreast of what’s happening. And these publications also set the tone when it comes to award season. Awards season is not something I particularly cover in my work, but it makes for a huge chunk of film-related journalism year-round. There’s a lot of money in awards coverage, obviously, in terms of advertising and sales.”

Editors who compete more directly with Penske’s trades have expressed more suspicions about the company’s modes of dominance. When The Daily Beast published an exposé about The Wrap’s editor-in-chief Sharon Waxman’s management style in 2021, her then-executive editor Thom Geier suggested that Penske might have had something to do with the accusations coming to light. “I’d be curious to know how many of the people that you’ve spoken to who have complained about Sharon Waxman and The Wrap are now working for Jay Penske,” Geier told The Daily Beast, adding, “We’re the last of the independent trades, and the only one that isn’t funded by a Saudi government that murders journalists,” a reference to the $200 million investment Penske received from the Saudi Research and Media Group in 2018. In that article, The Daily Beast labeled Geier’s suggestion “baseless.”

Competitors, including The Wrap, have also regularly wrangled with Penske over what they perceive to be talent hoarding via non-compete clauses. Upstart film industry newsletter The Ankler has bumped against that problem with a dispute with Penske in 2021 after announcing it had hired Tatiana Siegel from The Hollywood Reporter. After the dust-up settled, Siegel first landed at Penske-owned Rolling Stone before joining Penske-owned Variety as executive editor for film and media. Still, Ankler founder Richard Rushfield saw a competitive edge in his publication’s independence from the trade monolith. “If you’re at a publication like Variety, for example, the number of things a studio has over you is hard to keep track of,” he told The New York Times last year. “Publications with different business models, and more aggressive reporting, can elbow their way in.”

Of course, one of the pitfalls of consolidating within an industry niche is that Penske’s fortunes are tied to that sector’s ebb and flow. Observers of the commercial side of the art world were skeptical that Penske’s clutch of Artforum, Art in America, and Artnews could hold as much sway as his entertainment trades do. “Those magazines have all gone out of style,” said Asher Edelman, founder of art finance firm ArtAssure and, in his corporate raider days, an inspiration for Wall Street’s Gordon Gekko. “It’s been a long time since people paid much attention to any of those magazines — maybe The Art Newspaper a little bit, but that’s also a very small business,” he told The Fine Print. “I know that because I looked at buying it. It’s a small-potatoes world. ”

Hrag Vartanian, co-founder and editor-in-chief of Hyperallergic, concurred. “I think you think Artforum is a bigger deal than it is in our field.” That’s partly because of how the art market is structured, he said. Unlike Hollywood, which is itself dominated by a handful of studio behemoths, the art market is primarily made up of much smaller companies. “We’re not a field dominated by corporations quite the same as other creative fields. We’re still a field dominated by small businesses.”

And the players in the art world which make the most money — the mega-galleries and auctioneers that serve the richest of the rich — have themselves encroached on the space that establishment magazines like Penske’s once occupied. “Galleries and auction houses have created their own media outlets,” Vartanian noted, “Artnet is an auction house, as an example. Gagosian has their own magazine. Hauser and Wirth has their own magazine.” And unlike in the film world, where industry-spawned publications like Netflix’s Tudum have resulted in embarrassing failures, these publications have gained a sizeable cut of the art world’s attention. “I would guess that Artnet has much larger circulation for their publishing than any of these places,” Edelman said. “All these predictors of the art market just read what Sotheby’s and Christie’s write and reprint it anyway.”

Penske doesn’t cut a looming figure in the art world. “I didn’t realize [Penske] was a person,” Vartarian said. “I just thought it was a corporate name, until more recently. No one knows anything about him. I was talking to a friend in a gallery today. They didn’t really know anything about it either — and it’s a Chelsea gallery, it’s not like it’s so out of the way.” You’d imagine that’d be galling for a man who one Hollywood acquaintance told Insider, “likes being at the center of these industries in a way that gives him the appearance of power.” But with so many oddballs with outsize pockets regularly blundering through the art world, Penske sort of blends into the crowd. “He doesn’t seem that significant in terms of really rich dude doing quirky things,” Vartanian said. “Peter Brant is the guy before who’s similar. He owned both [Art in America and Artnews]. Art in America became his party outfit that his kids would throw parties around. Now he has his Brant Foundation for the arts. I think this is just very common in our field. It doesn’t really raise a lot of eyebrows.”

Penske’s seeming lack of interest in book trades rang some odd bells for some of his former employees. When Penske Media bought Artforum, it didn’t buy its sister publication Bookforum, and the magazine announced that its most recent issue would be its last. Jettisoning the book reviewing bastion seems an odd move for a man who counted Dragon Books, an antiquarian bookstore in Bel Air, among his early ventures. Chad Reingold, who managed the store for about a year, recalled visiting a storage unit that contained part of Penske’s private book collection. “It was a large storage unit and it was books and books and books and boxes and boxes and boxes,” he said. “Any collector, you open the door to their houses and it’s like the stateroom scene from Night at the Opera, it just comes pouring out.” How many of the 28,000 or so tomes that Penske collected, by Vanity Fair’s count, did the former manager think his boss had actually read? “My sense was that he was a voracious reader,” he said, “but he was so busy with his various business endeavors that how much time did he have to read?”

Through Penske’s visits to Dragon Books about once a week or once every other week, Reingold and the rest of the staff got a sense of his interests as a collector, which included obsessions with H.L. Mencken as well as Richard Feynman. “He would chase him at auction,” Reingold said. “I think he just liked the way that Feynman’s mind worked — that he was not only a brilliant physicist but that he was also a humanist. I think that appealed to Jay.” A page on the bookshop’s site, archived on the Internet Archive’s Wayback Machine, featured a list of “people we like” which seemed to reflect Penske’s personal interests and included, alongside Feynman and Mencken, artists Hieronymus Bosch, Francisco Goya, Diego Velasquez, and Pablo Picasso. However, Reingold noted, “I don’t recall discussing Picasso or artists very much with Jay.”

Still, as an independent publication, Artforum has been a venue for coverage of experimental, independent, and avant-garde films that matched Film Comment’s thoughtful approach. “I don’t know that I’m worried about how Artforum will change editorially. Obviously, these developments make you concerned about how leadership might change. Anytime there’s new ownership, there’s often a shake up of staff and budget and priorities, and especially with Penske being a really major player, which owns these trade publications, there is a weariness about how that might change the business and managerial priorities, and how that might then trickle down to affect coverage,” Girish said. “These developments just emboldened me, personally, to want to make sure that nonprofit independent publications like ours continue to try and provide that alternative focus and voice.”