Skydance’s David Ellison in Talks to Acquire Bari Weiss’ The Free Press

 

Key Takeaways

• Skydance Media CEO David Ellison has held preliminary talks to acquire Bari Weiss’s The Free Press, though a deal remains uncertain .
• Discussions include a potential role for Weiss in shaping CBS News editorial direction (non-managerial), linked to Skydance’s pending $8.4B Paramount Global merger .
• The Free Press boasts ~1.5M subscribers, a $100M valuation, and focuses on centrist/independent journalism .
• FCC approval for Skydance-Paramount may require ending DEI programs, adding a CBS ombudsman, and shifting news resources to local stations .
• Weiss prioritizes editorial independence, complicating acquisition talks amid her attendance at the Allen & Co. conference with Ellison .

---

Skydance’s Potential Acquisition of The Free Press: Media Disruption Ahead?

1 What’s Happening with Skydance and The Free Press?

David Ellison, the CEO of Skydance Media, is in early discussions to acquire The Free Press, the online news outlet founded by former New York Times journalist Bari Weiss. These talks, reported by the New York Times, are preliminary—meaning no deal is finalized or guaranteed yet. Weiss has publicly emphasized her commitment to running The Free Press independently, which adds complexity to the negotiations .

The timing here’s notable. Skydance is simultaneously pushing to close its colossal $8.4 billion merger with Paramount Global, parent company of CBS News. That deal’s pending approval from the Federal Communications Commission (FCC), a process scrutinizing license transfers and public interest implications . Ellison and Weiss’s presence this week at the exclusive Allen & Co. conference in Sun Valley—a known dealmaking hub—fuels speculation that talks could accelerate .

Why this matters: Acquiring The Free Press would signal Skydance’s ambition to influence news media direction post-Paramount merger, leveraging Weiss’s brand of “independent journalism” that challenges mainstream narratives on issues like DEI, transgender care, and Israel .

2 Who Are the Key Players Here?

• David Ellison: Founder/CEO of Skydance Media, son of Oracle billionaire Larry Ellison. His pending acquisition of Paramount positions him to helm CBS News. He’s previously courted Weiss for a CBS role .
• Bari Weiss: Ex-NYT opinion writer who resigned citing ideological bias and bullying. Launched The Free Press (originally Common Sense) in 2021. Her platform champions viewpoint diversity, criticizes “cancel culture,” and publishes contentious pieces often sidelined elsewhere .
• The Free Press Investors: Backed by >30 investors, including Bobby Kotick (ex-Activision Blizzard CEO) and Yael Aflalo (Reformation founder). Raised $15M at a $100M valuation in 2024 .
• FCC Chairman Brendan Carr: Key regulator demanding concessions for Paramount-Skydance approval, like ending DEI programs and adding CBS News oversight .

Ellison’s outreach to Weiss isn’t new—he approached her in June about CBS collaboration. But folding her outlet into Skydance would amplify her influence far beyond advisory talks .

3 What Exactly Is The Free Press?

Bari Weiss co-founded The Free Press in 2022 alongside her wife, Nellie Bowles, and sister, Suzy Weiss. It’s evolved from a Substack newsletter (Common Sense) into a multimedia news platform with ~1.5 million free/paid subscribers, podcasts, live events, and video content. The outlet employs ~50 people .

Editorially, it positions itself as a counterweight to perceived liberal media hegemony. Its reporting often critiques DEI initiatives, questions gender-affirming care for minors, and publishes pro-Israel perspectives. Weiss’s departure from the NYT—via a viral resignation letter accusing colleagues of bullying—cemented its anti-establishment ethos .

Financially, it’s robust: a $100M valuation and profitability through subscriptions (free/paid tiers) and events. Unlike venture-backed outlets burning cash, its model appeals to acquirers seeking audience reach without financial baggage .

4 How Could This Impact CBS News?

Ellison’s talks with Weiss include a potential role shaping the “editorial sensibilities of CBS News”—not a managerial position, but an influential advisory one. This suggests Skydance envisions Weiss steering ideological tone without day-to-day oversight .

Such a move would ignite internal friction at CBS. Staffers already bristled over Paramount’s $16M settlement of Donald Trump’s lawsuit against 60 Minutes (over a Kamala Harris interview edit). Adding Weiss—a polarizing figure who’s criticized “woke media”—could deepen divisions .

Structural changes might follow too. The FCC could mandate an independent CBS ombudsman to monitor bias as a merger condition. Weiss’s involvement could dovetail with this, reframing CBS’s news approach toward her “heterodox” style .

5 What Are the FCC Hurdles for Skydance-Paramount?

The Paramount-Skydance merger must secure FCC approval for broadcast license transfers. Chairman Brendan Carr has signaled demands for major concessions :

• End DEI Programs: Carr calls DEI “invidious discrimination.” T-Mobile/Verizon recently ended similar programs to gain FCC approval. Skydance will likely need to comply .
• CBS Ombudsman: An independent overseer for CBS News content to address bias complaints—a top request from petitioners like the Center for American Rights .
• Shift Resources to Local News: Move editorial focus from NYC/LA to CBS’s local stations (e.g., Detroit, Pittsburgh), prioritizing grassroots reporting over national narratives .
• Staffing Guarantees: Unions demand 8-year employment guarantees for station staff—clashing with Skydance’s planned $2B cost cuts .

Table: FCC Conditions Likely for Paramount-Skydance Approval

Failure here risks derailing both the Paramount deal and a Free Press acquisition.

6 Why This Deal Could Reshape Media

Acquiring The Free Press would advance Skydance’s push into opinion-driven news, distinct from traditional outlets. Weiss’s subscriber base (1.5M+) offers a built-in audience for cross-promotion on CBS platforms or Paramount+ .

It also reflects a broader trend: ideological realignment in news. Weiss’s criticism of “liberal media bias” resonates with conservative-leaning audiences, a demographic CBS historically struggles to capture. Her involvement could rebrand CBS News as a “centrist” alternative .

But risks abound. Weiss’s followers value independence—merging with a conglomerate could alienate them. Similarly, CBS talent may revolt if her role sidelines existing leadership. The New York Times notes Weiss has rejected past offers to maintain autonomy; Ellison must reconcile this with his Paramount ambitions .

7 What’s Next? Possible Outcomes

1. Acquisition + CBS Role: Skydance buys The Free Press, Weiss advises CBS News. Probability: Medium. Aligns with Ellison’s vision but requires Weiss to compromise autonomy .
2. Content Partnership: The Free Press supplies CBS with segments/podcasts sans acquisition. Probability: High. Lower risk, satisfies collaboration goals .
3. Talks Collapse: Weiss retains independence; Ellison seeks other “heterodox” voices. Probability: Medium. Weiss’s resistance to managerial control is a hurdle .

FCC approval remains the linchpin. If the Paramount merger stalls, the Free Press deal likely does too. But Carr’s demands—like ending DEI—align with Weiss’s stance, suggesting synergy if Skydance concedes .

8 Frequently Asked Questions

Is Skydance definitely buying The Free Press?

Nope. Talks are early and non-binding. Bari Weiss values independence, making a full acquisition uncertain. Partnerships are likelier short-term .

What would Bari Weiss do at CBS News?

Per reports, she’d shape “editorial sensibilities”—influencing tone and coverage priorities—without managing teams or daily operations .

How does Trump’s lawsuit affect the Paramount deal?

Paramount settled for $16M, removing a legal roadblock. But FCC scrutiny continues, focusing on public interest conditions like bias oversight and local news .

Will the FCC approve Skydance-Paramount?

Likely, but with strict terms: ending DEI, adding a CBS ombudsman, and possibly shifting resources to local stations. These aim to address bias and accountability concerns .

How big is The Free Press?

~1.5M subscribers, 50+ employees, $100M valuation. Funded by 30+ investors including Bobby Kotick and Yael Aflalo .