Skydance in Early Talks to Acquire Bari Weiss’s Free Press

David Ellison, the chief executive of the media company Skydance, has recently held early discussions about acquiring The Free Press, the online publication co-founded by Bari Weiss, according to two people with knowledge of the talks.

Ms. Weiss, who started The Free Press in 2021 with her wife, Nellie Bowles, and her sister, Suzy Weiss, has positioned the company as a brash alternative to traditional media organizations. Mr. Ellison is trying to close Skydance’s merger with Paramount, the parent company of CBS News.

A deal between Skydance and The Free Press is far from certain. Ms. Weiss, a former opinion writer for The New York Times, has expressed a desire to run the site as a stand-alone company for the foreseeable future. Mr. Ellison’s attention has been focused on closing the deal with Paramount.

This week, the two are attending the annual Allen & Company conference in Sun Valley, which has historically been a deal-making hotbed. Allen & Company, an investment firm, is a shareholder in The Free Press, alongside the venture capitalists Marc Andreessen and David Sacks, and the former Starbucks chief executive Howard Schultz.

The company has more than 30 investors, who own relatively small stakes in the company. Other investors include Yael Aflalo, the founder of Reformation, and Bobby Kotick, the former chief executive of Activision Blizzard.

Terms of any potential deal under discussion could not be learned.

In recent months, a handful of media owners have reached out to Ms. Weiss for advice on ways to improve their media properties, and some of that outreach has led to discussions about acquiring The Free Press, one of the people said.

Mr. Ellison’s talks with Ms. Weiss include a variety of options in which the burgeoning media mogul could work with Ms. Weiss, one of the people said. Among the many options being discussed include Ms. Weiss’s taking on an influential role in shaping the editorial sensibilities of CBS News, though she would likely not join in a managerial capacity, one of the people said.

Status, a newsletter focused on the media industry, earlier reported that Mr. Ellison has discussed bringing Ms. Weiss to CBS News in some capacity.

As of last August, The Free Press had more than 50 employees and offices on both coasts. It also hosts a series of live events, brokering debates about topics including immigration and crime. The site now has roughly 1.5 million free and paid subscribers and creates podcasts and video.

One of the biggest challenges facing Mr. Ellison when he takes over Paramount could be managing CBS News, a storied news division that has lately been a locus of turbulence and dissatisfaction. The company recently agreed to pay President Trump $16 million to settle a lawsuit he filed that accused “60 Minutes” of misleading viewers by deceptively editing an interview with former Vice President Kamala Harris.

Skydance’s merger with Paramount is awaiting approval from the Federal Communications Commission. Brendan Carr, the chairman of the F.C.C., has been examining a “news distortion” complaint against CBS News over the interview with Ms. Harris.