Billionaire media veteran Barry Diller approached Warner Bros. Discovery last year with an overture to acquire CNN, injecting fresh intrigue into the media conglomerate’s high-stakes restructuring. The inquiry, which never advanced to Warner’s board, underscores persistent interest in the cable news network despite Warner’s firm stance that it remains off the market. As Warner prepares to spin off its cable assets into Discovery Global, Diller’s personal interest—separate from his role at IAC—highlights the value suitors see in CNN even amid cord-cutting pressures.

A Warner Bros. Discovery spokesman emphasized, “CNN was not and is not for sale” and described it as “an incredibly important part of the future of Discovery Global once it separates from Warner Bros.” Wall Street Journal. This rebuff came after Diller made repeated approaches, with sources confirming his ongoing interest, as reported by multiple outlets following the Journal’s disclosure.

The timing of Diller’s pitch predated Warner’s June announcement of its two-company split and its formal sale process last fall. Warner plans to sell its studios and Max streaming service to Netflix while spinning cable networks like CNN into Discovery Global. Meanwhile, Paramount persists with a $77.9 billion tender offer for all of Warner Discovery, encompassing the cable assets.

Diller’s Enduring Media Empire

At 83, Diller brings decades of deal-making prowess to the table. He ran Paramount Pictures in the late 1970s and early 1980s, overseeing hits like “Raiders of the Lost Ark” and “Cheers.” From 1984 to 1992, as chairman and CEO of 20th Century Fox, he launched the Fox Broadcasting Company and greenlit “The Simpsons.” Wikipedia. Later ventures included QVC, Expedia, and building IAC into a digital powerhouse with brands like People and The Daily Beast.

Diller eyed Paramount again in 2024 amid its sale process, though no deal materialized. His history of bold moves—from launching Fox against industry skepticism to pivoting into interactive media—positions him as a wildcard in CNN discussions. Analysts peg CNN’s value at around $4 billion based on comparable deals, though Warner executives view it far higher.

It remains unclear how Diller would finance a bid or if partners are involved. His 1.39% stake in IAC suggests limited personal leverage through that vehicle, raising questions about bid conviction amid Warner insiders selling over 7 million shares recently. AInvest.

CNN’s Financial Backbone

Warner disclosed in a recent filing that CNN expects $1.8 billion in revenue this year, climbing to $2.2 billion by 2030, with adjusted EBITDA holding steady at $600 million—dipping to $500 million in 2027 before stabilizing. TheWrap. New platform revenue, including CNN’s All Access streaming tier launched last fall, is projected at $600 million by 2030, offsetting a 4% annual decline in core carriage and ad dollars.

These figures, rare public glimpses into CNN’s books, come amid Warner’s proxy filing for the Discovery Global spinoff. Historical data shows revenue fell from $2.2 billion in 2021 to $1.8 billion in 2023, reflecting broader cable woes. Yet CNN anchors Warner’s carriage deals with providers, complicating any carve-out sale due to renegotiation risks and tax hits.

Warner resists isolating CNN partly for these reasons, viewing it as a linchpin for Discovery Global’s viability. The spinoff entity will include TNT Sports, Discovery channels, and Discovery+, with overall U.S. networks revenue at $9.9 billion in 2026, declining to $7.7 billion by 2030.

Bidding Frenzy and Political Crosswinds

Netflix’s $72 billion deal for Warner’s studios and Max excludes cable, leaving Discovery Global independent—though Paramount attacks it as inferior, pushing its full $108.4 billion all-asset bid. Warner counters that Discovery Global merits up to $6.86 per share. TipRanks. Diller’s interest fuels valuation debates as Netflix revised to all-cash Tuesday, reducing Discovery Global debt by $260 million on strong 2025 cash flow.

President Trump amplified the drama in December, stating CNN’s ownership must change regardless of Netflix or Paramount prevailing. He has privately pushed for management friendlier to him and Republicans, criticizing current leadership. CNN. Diller, a prominent Democratic donor and Trump critic, embodies the opposite—potentially clashing with White House preferences. Paramount, led by David Ellison with backing from Trump ally Larry Ellison, has signaled CBS News overhauls signaling similar intent for CNN.

Sources note other billionaires have probed CNN paths in recent years, though none advanced. “There’s nothing new about people being interested in the premier global news network, but there’s no good reason to sell CNN,” one insider told ABC17News. As Warner’s breakup unfolds over the next six to nine months, Diller’s persistence adds pressure amid stock stability and insider sales signaling caution.

Strategic Hurdles in Cable’s Twilight

CNN grapples with ad revenue and ratings drops from cord-cutting and programming shifts, yet its global brand endures. Warner’s filings project streaming offsets but warn of subscriber erosion across networks. Discovery Global’s pitch emphasizes content licensing—$580 million in H2 2024 versus a $200 million quarterly norm—as a monetization pivot around unscripted hits.

Diller’s track record—from Paramount’s golden era to Fox’s disruption—suggests he eyes CNN as a turnaround play, perhaps blending news with digital interactivity akin to his IAC successes. However, political headwinds, tax barriers, and carriage dependencies fortify Warner’s defenses. The saga echoes Diller’s 1990s Paramount loss to Viacom, now redux in 2026’s media maelstrom.