CBS’s postponement on December 21 of a 60 Minutes segment on the Trump administration’s deportation of Venezuelan men to a prison in El Salvador drew attention once again to the pressures and sensitivities facing legacy news organisations in a highly polarised landscape. Episodes of this kind, regardless of how one judges the editorial decision itself, have contributed to a broader questioning of authority and transparency in journalism. It is within this context of shifting trust and audience expectations that digital ventures such as The Free Press have emerged and grown, offering an alternative model to traditional structures.
The meteoric rise of The Free Press from a Substack newsletter to a fully-fledged media company has often been framed as an entrepreneurial fairy tale: a bold journalist, in this case opinion writer Bari Weiss, leaves a big corporation, speaks freely, and is rewarded by an audience hungry for truth. The numbers are real, but the story is incomplete. To understand how a newborn enterprise amassed over 100,000 subscribers in under a year and rapidly attracted capital, one must look beyond charisma or managerial prowess and examine the conditions that made such velocity possible.
A characteristic trait of mainstream newsrooms is a tendency to compress complexity into slogans, turn structural forces into morality plays, and soothe rather than explain. This is not the romanticised story of the lemonade stand that became a multimillion-dollar franchise in a fortnight. Nor is it the product of technocratic brilliance alone. It is the convergence of elite networks, political timing and post-Trump news-sector realignment.
Bari Weiss did not launch The Free Press as an unknown writer. She entered the market with significant symbolic capital: a high-profile resignation from theNew York Times, a public narrative about institutional capture and free speech, and a decade of visibility within elite cultural circuits. That matters. Today, audience migration is far more powerful than audience creation. Tens of thousands of early subscribers were not strangers discovering a new voice: they were readers relocating their attention and trust.
Symbolic capital alone does not explain scale. What lowered risk and accelerated growth was not a single financial mastermind but an existing constellation of elite relationships – philanthropic, technological and media-adjacent – that rendered the project safe. Ms Weiss did not need guaranteed success; she needed insulation from catastrophic failure. That assurance, often informal and rarely advertised, changes behaviour. It enables boldness, speed, and confidence. Capital does not rush toward vision; it rushes toward validation. Early traction did not persuade investors as much as alert them that this was a vehicle worth boarding.
The political dimension, often sensed but poorly articulated, is central. The Free Press was not a partisan outlet and did not function as a Trumpist design. On the contrary, its appeal lay precisely in its distance from Trump. The key audience was composed of readers repelled by Trump but equally disturbed by how the old news industry responded to him.
After Trump won the 2016 presidential election, trust in mainstream organisations fractured among educated, affluent audiences. Institutions became openly moralistic and dissent inside them increasingly punishable. By 2020-21, a new niche had emerged: readers seeking heterodoxy without populism, dissent without vulgarity and critique without tribal allegiance. That audience was small but extraordinarily valuable – subscription-ready, influential, underserved.
Timing was decisive. Founded by Weiss in January 2021, The Free Press launched eight days before Trump’s departure from office, when passions remained high but institutional credibility had not recovered. Had it appeared in 2017, it would have been drowned in resistance fervour; had it launched later, the space would already be crowded. The window was narrow, and it was taken.
The role of professional management must be placed correctly. They did not create demand or conjure an audience. Their contribution came later: professionalising operations, diversifying revenue, and translating founder-led success into an institution that advertisers, partners, and acquirers could understand. They did not turn a blog into a business; they transformed a profitable editorial project into a conventional company. That distinction matters.
The broader lesson is not about individual genius or managerial alchemy. It is about sequencing. In today’s information economy, voice and audience now precede institution. Trust is accumulated first; infrastructure follows. Elite power does not disappear when institutions decay – it migrates. When legacy outlets faltered after Trump, resources, attention, and legitimacy flowed toward new vehicles capable of carrying them.
The recent acquisition of The Free Press by Paramount Skydance adds a final, revealing layer to the story. In October David Ellison – CEO of Skydance and son of Oracle founder Larry Ellison, a long-standing ally and confidant of President Trump – brought Ms Weiss and her publication into a conglomerate seeking renewal after years of audience erosion. The group includes CBS news, where Ms Weiss now serves as editor-in-chief.
The personal proximity between the Ellison family and Donald Trump is not evidence of ideological control, but it is emblematic of a broader realignment: capital and influence once comfortably anchored in established institutions are now repositioning themselves through new, hybrid vehicles that promise both cultural dissent and elite respectability. That The Free Press – unreservedly opposed to Mr Trump as a bad custodian of power – would end up folded into a business empire led by figures adjacent to his inner circle underscores the paradox of the post-Trump media economy: disruption did not dismantle elite power so much as redistribute it across new channels and alliances.
The controversy at the helm of CBS News reached a crescendo on December 24 when Stephen Miller, White House deputy chief of staff, called the pulled report ‘another pathetic 60 Minutes hatchet job’. The intensity of the reactions, from opposing political camps, points to unresolved tensions within an emerging environment still struggling to reconcile authority, credibility and independence.
Many ventures that present themselves as alternatives to institutional journalism emerge in defiance of its perceived constraints. Yet their very success often draws them back into the same circuits of power, scale, and responsibility. This is less a matter of individual inconsistency than of structural gravity: as counter-institutional platforms expand, they must confront the persistent strain between independence and influence.
In that sense, The Free Press stands not only as a leading example of the new digital universe, but also as a reminder that escaping the gravitational pull of large corporate structures may be easier than permanently transcending them.
