Decades ago, Mike Bloomberg was having breakfast with a friend in Paris when he asked, “Do you think I could buy The New York Times?” His friend told him that the paper wasn’t sold in the hotel, to which Bloomberg offered a clarification: “No, do you think I could buy the Times?”

This amusing vignette first surfaced in a 2012 New York magazine article about the business magnate and his post-mayoral ambitions, in the 24th of 38 paragraphs. As Gabe Sherman noted in the piece, purchasing the Times was an oft-discussed next act for Bloomberg, though he had made no serious moves to obtain it. The article instead explored more realistic possibilities: running Bloomberg LP and running for president, both of which Mike did.

Mike’s croissant confab came to mind on Wednesday when The Wall Street Journal broke the news that Barry Diller had approached Warner Bros. Discovery last year to express his interest in buying CNN—not as a detail in a story, but as an exclusive. In the second sentence, however, it noted a few caveats: “No serious action was taken on Diller’s inquiry nor was it taken to the Warner board of directors.” Even that may have underemphasized the extremely casual nature of the overture: Diller, a friend of WBD chief David Zaslav, has indeed floated the idea to him on a few occasions, but there’s never been a pitch deck, no bankers involved, nothing beyond a hypothetical. And for what it’s worth, Warner’s official statement is that CNN “was not and is not for sale.”

It’s perhaps also worth noting that, in recent years, several well-known and would-be media titans have casually expressed to Zaz their interest in buying CNN. One of the more recent, I learned this week, is Elon Musk. (Fun, unrelated fact: Barry and Elon were in Zaz’s suite at the U.S. Open in 2024, along with none other than CNN’s own Fareed Zakaria.) Elon did not respond to a request for comment, but it’s hardly surprising that an irreverent centibillionaire who spent $44 billion to commandeer Twitter and bend it toward his political and media preferences wouldn’t be similarly piqued by paying a fraction of that to reengineer the world’s most prominent 24-hour global news network.

Anyway, Barry and Elon probably both knew the challenges ahead of any potential deal. First, selling CNN à la carte would trigger a massive tax bill, since it has almost no tax basis. It’s also not merely another asset in the Global Networks bundle; it’s the anchor tenant. If you strip it out, the economics of the remaining portfolio become far harder to justify, if not entirely untenable. If Zaz sells Warner Bros. to Netflix, Gunnar’s spun-out Global Networks business will need CNN’s revenue to offset its significant debt load. If the Ellisons prevail in their bid for all of WBD, they’ll require CNN’s $600 million in annual profit to service the debt they are raising for their bid—even as they shove it into the Bari Weiss meat grinder.

In its exclusive, the Journal amusingly strained to describe Diller’s overture to Zaz as “a new twist to the biggest takeover drama in the media industry in years.” The thoughtful news consumer might ask: Why is Diller’s very casual interest in CNN—which he first expressed last year, and which is very unlikely to manifest as anything real—suddenly materializing as an exclusive in the Journal? As you can imagine, the media elite have their theories.

Theory 1: A source just happened to hear Barry waxing nostalgic about it over coffee and gipfeli in Davos, and the Journal got a little over its skis. Theory 2: Warner Bros. Discovery is in the midst of a tug-of-war between Netflix and Paramount that hangs on the perceived equity value of the Discovery Global Networks stub, of which CNN is the cornerstone. And since the Ellisons are trying to convince shareholders that the stub’s value is somewhere between $0 and $1.40, perhaps Zaz and the WBD board wanted to remind everyone that CNN is a valuable and highly coveted asset. Reader, choose your own adventure. (Now-ubiquitous disclosure: Through our recent acquisition of Air Mail, Zaz is a de minimis investor in Puck.)

How valuable is CNN? In the Zucker era, when the network was netting more than $1 billion in annual profits, many analysts put its value north of $10 billion, assuming a 10-12x multiple on EBITDA. As I noted the other day, CNN has since fallen to just $600 million in annual profit—not great, Mark!—though part of the decline is due to hundreds of millions in new digital investments. If Zaz wanted to prep the network for a sale, he could conceivably get the profits back up to around $800 million–$850 million. Even then, though, it’s not clear that the network would still command that 10-12x multiple given the audience fragmentation and myriad misguided strategic resets that have damaged the brand. (I’ve written a few articles about this; Chris Licht has the exact number.) Anyway, a brand premium has likely turned into a legacy discount.

And yet, despite the inexorable decline and the brand cachet withdrawals, CNN remains a valuable asset—and a trophy asset, as Barry and Elon’s casual interest attests. It’s not hard to imagine a wealthy, motivated buyer sprinkling a few extra billion on top of the actual enterprise value, especially if they’re under the illusion that they can grow the business. Fox News does around $2 billion in EBITDA, with an implied value of around $20 billion; presumably, this fantasy buyer would be convinced they could lift CNN to similar heights.

The far more likely outcome, of course, is that none of this happens—that Zaz and Netflix get their deal approved by regulators, Gunnarco spins out to an uncharitable public market, and the independent cable players circle each other as they are simultaneously circled. In this scenario, CNN eventually finds its way into the loving arms of Apollo, which ties it up with Yahoo!—another once-indomitable brand that has enjoyed a recent resurgence after a decade of leaking helium—or another private equity firm that then accelerates the value extraction. Actually, on some level, Diller may know this. This value extraction guided the second act of his career, from QVC to People. Not his problem now, though…