Part 2 of 8: Political Orphans — The Ideological Castaways
The independent media ecosystem isn’t one thing. It’s a collection of different business models, personalities and audience relationships. I’ve spent over a year pulling back the editorial curtain on the creators within this new information economy and studying it the way I’d study any other audience-acquisition machine. Because that’s what it is.
Every personality, platform and media company is competing for the same scarce resource: your attention.
They’re building audiences, creating relationships, establishing credibility, triggering emotion, encouraging habits and ultimately influencing what people think, share and do. That doesn’t mean they’re all manipulating you. Many are doing important work. Some are excellent journalists. Some are educators. Some are investigators. Some are commentators. Some are entertainers who have become incredibly influential in politics.
But good intentions don’t make anyone immune to the machinery.
As a marketer, I can’t unsee the mechanics: the hooks, credibility cues, psychological levers, one-way relationships, identity signals and engagement incentives that keep people watching, subscribing and sharing. So, I’m using my experience and marketing instincts to examine this ecosystem, and the information economy behind it through the lens I know best: how attention is captured, trust is built, audiences are cultivated, and influence is created.
Not to tell you who to trust. Not to tell you what’s left or right. Not to declare which creators are good or bad. Instead, I’m interested in understanding and sharing how the machine works, and why it works on us.
Only you can decide who you will trust.
Over the course of this series, I’m breaking the independent political-media ecosystem into six broad personas. I will be examining what each one offers its audience, how each builds trust, what psychological levers it tends to pull, and where the model can become both powerful and problematic.
This installment looks at Political Orphans. These are the insiders, commentators and former political loyalists who found themselves increasingly estranged from the movements or institutions that once gave them a home.
Political Orphans
The Ideological Castaways
Political Orphans have experienced a rupture with their original political tribe, carried their institutional credibility into a new political identity, and successfully built an independent media platform capable of acquiring and retaining a new audience.
Every political movement eventually produces people who no longer recognize the movement they helped build. When that break happens, the old audience doesn’t usually stick around. Sometimes it walks away. More often, it’s taken away, revoked by the very institution that once applauded them. So, they go looking for a new one. Not just because they need a platform. Because somewhere, they still need to be told they were right.
These are the Political Orphans of independent media: former insiders, pundits, politicians and commentators who find themselves politically homeless and decide to pivot to a new audience outside the institutions that once gave them a platform.
They know the tribe from the inside. That gives them something most independent creators spend years establishing. Credibility. They know the personalities, the institutions, the language, the history. They know what their former allies believe, and perhaps more importantly, what those allies are reluctant to say publicly.
But the same insider knowledge that makes them credible also makes them suspect. A new audience applauds the arrival, but underneath the applause there’s a quieter question that never fully goes away: is this person actually one of us now, or just passing through? Political Orphans rarely get the unconditional trust a lifelong member of a tribe enjoys. They’re useful. They’re interesting. They’re often embraced enthusiastically. But they’re also being watched carefully for the moment their old instincts resurface, for the line they won’t cross, for proof that the break was real and not just convenient.
That scrutiny never fully lifts. Every policy position gets quietly cross-referenced against their old affiliation. Every hesitation gets read as a tell. Every disagreement with the new audience risks being reinterpreted not as an honest difference of opinion, but as evidence the conversion was never complete.
An insider everywhere. Fully trusted nowhere.
The basic proposition: “I know what happened because I was there.”
Political Orphans occupy an unusual position in the information economy. They aren’t outsiders. They aren’t quite insiders anymore either. Their appeal often rests on a simple proposition:
I haven’t abandoned my principles. The movement I once belonged to changed.
Their politics and reasons for leaving their original base audience aren’t interchangeable. The common thread isn’t a particular ideology. It’s political displacement of any flavor.
You can see variations of the Political Orphan proposition across very different projects: The Bulwark, The Warning (Steve Schmidt), The Kinzinger Report, The Lincoln Project, and the independent work of figures like Matt Taibbi, Glenn Greenwald, Charlie Sykes, Joe Walsh, Jennifer Rubin, Bari Weiss, and Breaking Points’ Krystal Ball and Saagar Enjeti.
In nearly every case, the creator has a story about how they became politically homeless and that story becomes part of the product. The chart below includes some of the most popular Political Orphans in today’s independent media ecosystem ranked by combined audience reach across all their social and independent media platforms.
Why audiences find them compelling
Political Orphans solve a specific problem for an audience: What if I still believe what I used to believe, but I no longer trust the people who are supposed to represent it?
That’s a powerful psychological position. It gives an audience permission to change loyalties without changing its underlying identity. A conservative who no longer recognizes the Republican Party can still think of himself as conservative. A liberal disillusioned with progressive politics can still think of herself as liberal. A former partisan can criticize the tribe without feeling like she’s joined the other one.
The creator becomes a kind of identity bridge. And that bridge can be extraordinarily sticky, because the audience isn’t simply subscribing to someone’s analysis. They’re subscribing to a way of understanding their own political displacement.
But there’s a second audience here, and it’s arguably even more enthusiastic than the first: the opposing side. When a lifelong Republican breaks publicly with the GOP, Democrats don’t just gain a useful ally, they gain a witness. A Never-Trump conservative validating a progressive critique of Trumpism lands differently than the same critique coming from a Democrat, because it isn’t partisan anymore. It’s a confession. The opposing audience doesn’t hear “I changed my mind.” They hear “you were right about us all along, and now someone from inside is finally admitting it.”
The same holds in reverse: when Glenn Greenwald or Bari Weiss breaks with progressive orthodoxy, conservatives don’t hear a change of mind either. They hear the left finally admitting what the right had been saying for years.
That’s a different kind of stickiness than the identity-bridge function above. The original audience uses the Political Orphan to preserve an identity. The opposing audience uses the same Political Orphan as corroboration and proof. Political Orphans that speak out are evidence that their own long-standing suspicions about the other side were never partisan paranoia, but simply true. That’s a little different hunger than the audience’s need for belonging or identity. The audience wants to feel understood. The creator wants to feel exonerated. And when those two needs line up, the result is one of the stickiest relationships in independent media.
A single Political Orphan can therefore build two audiences at once, for two entirely different emotional reasons, without ever having to choose between them.
The credibility advantage
Political Orphans have an advantage native digital creators often work years to build. They leverage their institutional memory.
Someone who spent decades inside partisan politics, journalism, or a political movement can explain things that aren’t obvious from the outside. They can say: this is how the institution actually works. This is what that person used to believe. This isn’t normal. Here’s what you’re missing.
That insider perspective can be genuinely valuable. It can also create a credibility shortcut: they were there, therefore they know. But here’s the rub: those aren’t the same thing. Being inside an institution gives someone access to information and experience. It does not make every subsequent interpretation correct. Experience is evidence. It isn’t proof.
In addition to their insider advantage, a Political Orphan’s reach is rarely confined to independent media platforms. Many Political Orphans don’t just build an independent audience. They remain fixtures on the very networks and shows that once defined their careers, appearing as pundits, panelists, and guest commentators. Bill Kristol and David Frum circulate through cable panels regularly. Charlie Sykes and Tim Miller show up across MSNBC and other mainstream outlets as “anti-Trump conservative” commentary regulars. This matters because it means the audience numbers on any one platform such as a Substack subscriber count, or a podcast download figure understate the real reach.
A Political Orphan’s influence often shows up twice: once in the independent platforms they built, and again every time a legacy booker invites them back as the credentialed voice of dissent from their own former side.
That dual presence is also a credibility amplifier. A rather unique superpower of this independent media category. To be invited back onto mainstream television as “the reasonable [former party] voice” reinforces the very insider-credibility claim this whole category depends on. The legacy institutions are effectively co-signing the orphan’s authority, even while that orphan is building an audience explicitly premised on distrust of legacy institutions and their own past political alliances.
The psychological machinery
This category has some particularly powerful persuasion mechanisms.
1. Insider knowledge
The creator gives their audience the impression they possess information the audience doesn’t have. A subtle form of exclusivity. You’re hearing this from someone who was actually in the room. It’s one of the oldest persuasion mechanisms there is: information feels more valuable when it feels scarce. Charlie Sykes built 23 years of Wisconsin talk-radio credibility before turning it toward The Bulwark and now his newsletter To the Contrary. The value of his critique rests entirely on having once been a true believer.
2. Betrayal
Political Orphans frequently have a story about something that changed. The party betrayed its principles. The movement became something else. Betrayal is emotionally potent because it transforms a political disagreement into a relationship story. It’s no longer “I disagree with them.” It’s “I trusted them, and they changed.” Liz Cheney’s arc from GOP leadership to losing her seat for refusing to move with her party is the starkest version of this: the betrayal isn’t abstract; it cost her the career.
3. Moral courage
“I’m willing to say this even though my own side won’t like it” can be a legitimate marker of independence. It can also become the brand. The creator who repeatedly demonstrates willingness to criticize their former tribe becomes associated with courage and authenticity, until being the person who says the uncomfortable thing becomes almost as important as the thing being said.
Adam Kinzinger is a useful case study here. When asked whether other Republicans privately agree with him but stay silent, Kinzinger’s go-to answer is some version of “I’m not courageous, I’m surrounded by cowards.” It’s a genuinely sharp point about his party. It’s also, repeated often enough to become a tagline. One that positions every subsequent Kinzinger statement as an act of bravery before anyone has evaluated whether the statement itself is correct.
4. Tribal rehabilitation
Perhaps the most interesting lever. Political Orphans let audiences preserve parts of their identity while abandoning parts of their political tribe. A psychological off-ramp. You don’t have to say “everything I believed was wrong.” Instead, you can say “the movement changed, my principles didn’t.”
Breaking Points’ entire premise runs on this mechanic for people estranged from both parties’ establishments at once. Think of it like two kids from different households who end up at the same table, each insisting they didn’t run away. Their parents just stopped acting like parents. Krystal Ball represents the populist left, orphaned by a Democratic establishment she sees as corporate-captured. Saagar Enjeti represents the populist right, orphaned by a Republican establishment he sees as abandoning its own working-class base. They disagree about plenty. But they agree on the shape of the betrayal.
And that’s exactly what their audience gets to do too. A lifelong progressive can watch Ball and think I’m still progressive, the party just isn’t anymore. A lifelong conservative can watch Enjeti and think the same thing about the GOP. Neither has to walk anything back. They just needed someone to go first.
5. Belonging
And here’s the irony: the creator may have left a tribe only to build a new one. The audience becomes a community of people who see themselves as politically homeless, independent, or unwilling to follow either party blindly. The new identity: we’re the people who still believe the old principles. We’re the ones who aren’t fooled. That’s still tribal identity. It’s just a different tribe.
The Bulwark doesn’t even hide this. It’s baked into the branding. The outlet describes its own audience as “the reality-based community,” and its pitch to readers is a simple promise: we’ll keep you sane. That’s not a policy platform. It’s a tribal membership card. The implicit claim isn’t “agree with our takes,” it’s “join the people who didn’t lose their minds.” Readers aren’t signing up for center-right commentary. They’re signing up for a label that lets them feel like the last sane person in the room.
Charlie Sykes, an original Bulwark co-founder, runs his own show now on the exact same premise, down to the sign-off. To the Contrary is tagged, in full: “You are not the crazy ones.” He closes episodes reminding listeners of the same thing. It’s not a policy argument. It’s a nightly reassurance. Membership renewed, one more time.
6. Vindication
Political orphans need to find a new audience. That search isn’t just about survival. It’s about settling a debt that was never paid.
Political Orphans didn’t choose to leave quietly. Most were pushed, discredited, or watched former allies turn on them in public. The new platform isn’t just a business. It’s a case being built in real time. Every subscriber is a juror. Every view, a small verdict. Every “I told you so” moment such as a policy failure, a scandal, a reversal from a former ally isn’t just content. It’s evidence.
I was right. You’ll see it too, eventually.
But here’s the part worth sitting with: vindication is not an admission of being wrong. It’s the opposite. The core objective isn’t to update a position. Political Orphans want to prove their original position was correct all along, and that everyone else simply failed to see it. Don’t mistake the new platform for a new outlook. In most cases, it’s the same outlook and belief system, just relocated. The independent platform often becomes a megaphone for beliefs that were never really renounced but became unwelcome in the room they used to stand in.
The upside
There’s a lot to like here. Political Orphans provide something traditional partisan media often can’t: internal criticism. They challenge former allies in ways outsiders can’t. They preserve institutional knowledge that might otherwise disappear. And they create space for people who genuinely don’t fit the current partisan structure. In a media environment dominated by ideological sorting, that’s useful. Sometimes the person best positioned to explain a movement is the person who just left it.
The downside
Independence isn’t the same thing as neutrality. A person can leave one tribe and retain strong ideological commitments. Rejecting their old movement while developing a new set of assumptions just as firm.
The trouble is that the new audience rarely sees it that way. A lifelong Republican who breaks with the GOP doesn’t suddenly become a Democrat, but a progressive audience, grateful for the validation, often treats them like one anyway. The creator becomes an honorary member of a team they never actually joined. They may still oppose abortion, still want lower taxes, still favor a more hawkish foreign policy. None of that disappears just because they broke with Trump. The applause rarely distinguishes between “I left my party” and “I joined yours.” More importantly, the creator has little incentive to correct the misunderstanding, since the warmth of being newly welcomed is the whole point.
Once an audience gathers around that misunderstanding, there’s real pressure to keep it alive. The newsletter needs subscribers. The algorithm needs engagement. The audience rewards certain interpretations more than others, an incentive that has nothing to do with sincerity. The market can reinforce a worldview nobody set out to manufacture.
The Lincoln Project is a sharp example of how far that pressure can travel. Reporting found that roughly $1.5 million of the $4.9 million it spent between the 2024 election and mid-2025 went to firms owned by its own leaders. Including payments to a media company run by co-founder Rick Wilson. Nobody necessarily set out to build a donor-funded enterprise that quietly pays its own founders. But once a political-exile brand exists, and donors keep funding it, the incentive to keep the brand (and the checks) alive doesn’t require anyone to be dishonest. It just requires the machine to keep running.
What should we watch for?
When I consume a Political Orphan, I believe there are five questions worth asking:
- What did this person actually experience firsthand?
- What changed: their principles, the movement, or both?
- Are they criticizing their former tribe consistently, or selectively?
- What does their audience reward?
- And perhaps most importantly: what identity am I being invited to join?
Answer all five honestly, and you’ll know exactly what you’re buying.
The paradox of the Political Orphan
The fascinating thing about this category is that it can begin with genuine independence and still develop its own tribalism. Someone leaves an institution because they no longer feel at home. They build an audience around that experience. The audience finds others who feel the same way. A community forms, develops shared assumptions, and the creator becomes its trusted interpreter.
Eventually, the orphan gets adopted by a new tribe.
That doesn’t make the creator dishonest. It makes them human. And it’s why independent media requires a different kind of media literacy. We shouldn’t just ask whether someone is left, right, independent, or partisan. We should ask: what is this person uniquely positioned to tell me? What incentives surround them? What emotional need does their content satisfy? What might I be accepting simply because I trust the person delivering it?
The goal isn’t to become cynical about independent media. It’s to become conscious of the machinery. Because independent doesn’t mean influence-free. It doesn’t mean incentive-free. And it certainly doesn’t mean tribe-free.
There’s a larger story of the Independent Media Machine.
Every creator has a story. Every audience has a reason for being there. Every platform has an economic model. Every algorithm has an incentive. And every message exists inside an information economy designed, intentionally or not, to capture attention, build trust and influence what we believe.
So, the question isn’t simply“Do I trust this person?”It’s, “What is the machine around them encouraging me to believe?”
On that note I’ll leave you with a quote from the environmentalist Paul Watson:
“It doesn’t matter what is true, it only matters what people believe is true.”
Stay educated. Think critically. Because every truth should matter.
