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Mr. Diller, a digital media pioneer, lost a bidding war for Paramount Pictures decades ago. Now, he’s making a run at its parent company.

Paramount’s board of directors, which was already deep into talks with the media company Skydance, didn’t engage with the offer.

David Ellison, the founder of the Skydance media company, met with Paramount’s board of directors late last month to discuss the deal.

The cable company acquired the network, once billed as “CNBC for millennials,” in 2019 for $200 million.

The company was part of a group of bidders that offered $225 million to acquire the bankrupt media company.

Vice, which had wooed media giants, has struggled to adjust to the punishing realities of digital publishing. A group of creditors could buy Vice for...

The company, which was once valued at $5.7 billion, has been struggling to find a buyer this year.

Yahoo’s chief executive sees the deal as a long-term bet on digital advertising. The companies estimate that their ad partnership will generate $1 billion annually.

The group of bidders includes investors from the United States and overseas, a company spokesman said.

The century-old business magazine had aimed to go public through a blank-check company based in Hong Kong but changed course after the market flipped.