In this episode of Reality Checking the Bulwark, Evan and I analyze Tim Miller’s style of political storytelling, using his own writing in Why We Did It: A Travelogue to the Republican Road to Hell as our backdrop. Miller has written candidly about coming from a Washington D.C. professional tradition that prioritizes the game of electioneering over actual governance, it is one that reinforced racist and homophobic campaign tactics because winning mattered more than leading.

Miller was a hatchet man for GOP PACs and the RNC, attacking Democrats even when those attacks targeted people like himself. His dissonance stems from a belief that he could compartmentalize his sexuality and that he didn’t need to be as open as other gay men, but still could win the game of D.C. career elevation, even when that game came at the direct expense of his own right to marry who he loves.

That dissonance persists today. He tries to square three irreconcilable things: belief in a version of America that never existed, loyalty to a professional game that was always rigged against him, and the quiet truth Trump’s victories revealed about the bigoted foundation of conservative politics. Sometimes he disappoints by playing into right-wing frames. Sometimes he surprises.

My conclusion is that Tim Miller is best understood as an artifact — a peculiar and revealing outgrowth of the pre-collapse conservative professional class that briefly found a home in the pro-democracy coalition. The game never stopped for Tim. He just changed teams. Now he plays for reactionary centrism, punching left and laundering right-wing frames as reasonable moderate opinion for an audience that finds that reassuring.

He's worth analyzing carefully.

He's just not always useful in charting the path forward.

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We discuss how these narratives can flatten voters into caricatures, obscure deeper historical forces, and narrow the imagination of our national discourse at the very moment we need it most.

I hope you enjoy this stimulating conversation.

Please subscribe to and share Walter’s Substack, and continue supporting audience-driven media.

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There are two narratives that I have come across. Trump-adjacent spokespeople are dispelling the popular notion among anti-Trump groups that Iran has humiliated President Trump because it shows its control over the Strait of Hormuz. Actually, the entity that controls the Strait of Hormuz is the insurance underwriting i…

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Last night Ken Paxton defeated John Cornyn.

James Talarico posted this:

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Today, the flags fly at half-staff, and the names get read aloud, and somewhere a teenager who enlisted because the recruiter came to his high school and the recruiter’s office was warmer than his mother’s apartment will be told that he is part of a tradition. That tradition is real. So is the story that surrounds it, and the …

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Charlie Sykes also has a darker history. He was one of the main engines of Trumpism, having spent more than two decades pumping grievance and coded supremacy politics into the Milwaukee airwaves before Trump ever rode an escalator. According to assessments by people who watched Wisconsin at the time, there would have been no Scott Walker without him. The talking points that catalyzed Act 10, the school voucher fight aimed at Milwaukee’s majority-Black public schools, the welfare-state critique that gave Wisconsin conservatism its racial vocabulary without ever requiring it to say the words, were the infrastructure that undergirded his show.

And yet, having met him and listened to him for years, I think Sykes is genuinely a good man — a good man who was part of a toxic political communications assembly line. He is well-read, witty, and one of the smartest voices in the Never-Trump constellation. But his opinions increasingly come off as inaccurate artifacts of a political moment when America felt triumphant but didn’t notice, or didn’t want to notice, what it was doing to its own people to sustain that triumph.

In this episode of Reality Checking the Bulwark, Evan and I have decided to analyze the individuals who comprise (or once comprised) . Charlie has since left and now writes his own Substack called To the Contrary, which is worth following. But we often find ourselves frustrated by takes that come off like stale Cold War microwave food: a punch to the left, a claim to the lost nobility of the right, reheated and served as fresh analysis.

In my harshest reading, I find myself wondering whether Charlie sits in a longer American lineage, whether he is one in a line of useful idiots for the neo-Confederate cause, men who used Edmund Burke and the language of prudence and gradualism to intellectualize something far darker and far more ancient to American life. The Milwaukee suburbs whose worldview his show served were not generic conservatives. They were the geographic and political descendants of an American racial settlement, and the philosophical machinery he supplied them with, one of order, responsibility, and the warning against utopian leveling, was, in its functional effect, the same machinery the post-Reconstruction Redeemers had used a century earlier to dress an older project in respectable clothes.

I still recommend Charlie’s commentary with a grain of salt, and so far, he still recommends Stew On This. But I am wary of him and others in his category of political storyteller because their continued usefulness to the national discourse seems to depend on a strident retelling of a noble Reaganism rather than on an accurate historical record of where Trumpism actually came from. The story has a hero, and the hero is very much like the storyteller.

I present to you: Reality Checking the Bulwark — Charlie Sykes.

Join us Next Time for Reality Checking the Bulwark - Tim Miller

LIVE: May 24, 2026 at 3 PM ET

Please read the companion piece as well:

Author’s Note: I am now writing under a pseudonym, Deuce Davis.

Learn more below.

Previously on Stew On This:

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The conventional wisdom among the commentariat is that because of inflation and anti-incumbent energy internationally, Democrats were destined to lose in 2024. There are reasons to hold onto this specific truth, especially the part abou…

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Author’s Note:

Starting with this post, I'll be writing here as Deuce Davis.

Steward Beckham Jr. has accumulated too many hats across civic, professional, and personal life, and a pen name, even one as transparent as this one (the days when Hamilton could really be Publius are long behind us), still buys a margin of separati…

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There is a new poll being discussed…

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Strange Fruit

Learn Something New Today is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber…

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a month ago · 69 likes · 3 comments · Anthony M.

Anthony brings the past forward into the present by explaining the long restorative struggle of the Confederacy through anti-Black political movements and cultural signaling. We should not be surprised that the rollback of rights have moved at such a rapid pace when we dare to look at the unvarnished truth of white supremacy in American life and history.

I hope you read Anthony’s article and subscribe to his substack! Enjoy this conversation and have a great weekend!

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I took a break from writing after the Voting Rights Act was gutted, again. It was a heartbreaking display, and I had a feeling it would be met with the same milquetoast centrist call for Democrats to reach out to more Trump voters rather than reckon with the fact that this destruction of civil rights protections is o…

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It used to invoke the full and final form of a system so inherently monstrous, so inhumane, that it eats itself after finally consuming every limited input – including people – that made it churn. Like Francis Fukuyama’s “end of history,” the phrase “late-stage capitalism” has migrated from its once marginal position and become such a handy description of everyday life, it’s now a cliche.

The language itself has been consumed for every last drop of meaning.

“Enshittification” is the new “late-stage capitalism.” Coined to describe the digital product lifecycle of diminishing quality, the term has been embraced and broadly applied as the new shorthand for anything that was once good but no longer is. Like the United States:

In the Enshittified States of America, The Bulwark’s Jonathan V. Last laments that the country has gone slowly downhill since at least the turn of the century, as evidenced primarily by government ineptitude and the erosion of democracy. Once upon a time the United States functioned to serve its citizens, then operated in service of both its citizens and its international partners, eventually came to serve only the global system itself, and now finally – according to Last – serves no one and no thing.

In his conclusion, Last gestures to the will of the voters for partial responsibility for our national self-destruction. But the bulk of the blame (and the bulk of the essay) is devoted to “structural barriers” and a political system in which both parties share equivalent responsibility for its dysfunction.

Conspicuously absent is the particular impact of the Republican party.

Every problem is understood as an equivalent and balanced responsibility shared by Democrats and Republicans. Yet as far back as 2012, renowned independent political scientists Norman Ornstein and Thomas Mann identified the GOP as “an insurgent outlier – ideologically extreme; contemptuous of the inherited social and economic policy regime; scornful of compromise; unpersuaded by conventional understanding of facts, evidence and science; and dismissive of the legitimacy of its political opposition.”

Ornstein and Mann said it plainly in 2012 – and it’s only compounded in the fourteen years since: the Republicans are the problem. They are disproportionately responsible for every crisis JVL listed above.

No serious thinker still believes the long-debunked both-sides fallacy, let alone publishes it to their million-subscriber Substack. So why is the typically clear-eyed JVL arguing that fixing immigration, the Supreme Court, and gerrymandering are all “impossible to achieve at scale because of our system’s deep sclerosis”?

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There is a real villain in this story. But acknowledging how we truly got here would require JVL to not only cite Ornstein and Mann in the Obama era when his Bulwark colleagues were professional GOP operatives, but also to indict the party’s wholesale assault on democratic norms as far back as the Gingrich revolution. So instead we get systemic issues with a passive voice.

Not to deny the Democrats’ role in our national decline. They deserve plenty of blame – but only insofar as the party has followed the Republicans’ lead hollowing out our economy, our environment, our public health, and our constitutional rights. This forty-year project of pulling the country steadily to the authoritarian right recontextualizes Trump as the logical end product of everything the Bulwark staff were committed to before they left the party in 2016.

The Bulwark can never confront or reckon with this central, deeply inconvenient fact. Individual members of the organization may have grappled extensively with their complicity in the party’s decades-long radicalization. But the personal mea culpa means little when the ideological worldview that guaranteed Trumpism’s rise remains intact. And so we get essays like this one from JVL. Clever. Articulate. Topical. And wildly discordant with the empirical realities of the politics it purports to address.

This essay can be summarized as: America was once decent, now it isn’t, the barriers to self-improvement are structural and systemic, and there’s nothing to be done about it.

Is JVL publishing rank nihilism? More than ten years into a Trump era in which the Bulwark Republicans just lose and lose and lose, what even is the point of the publication? They lost the GOP to Trump. They lost the 2024 election running precisely the campaign their worldview prescribed. They are losing the argument about the Democratic Party’s future to the insurgent left they spent years condescending to. At some point the people who are always wrong about everything don’t get to keep framing themselves as the savvy oracle of the pro-democracy movement.

If the novelty of the Bulwark has long worn off, and the collective wisdom of their political prognostications proves consistently antithetical to actual democratic outcomes, the only remaining value of the organization is the financial benefit of the founders and investors themselves. The purpose of the JVL piece is to feed the subscriber base and bring in new paid subs. It doesn’t have to make any sense. It’s just slop.

The Bulwark itself has become enshittified. Whatever value it once provided its subscribers has long dried up. Its only remaining purpose is to make money for its staff. Let’s not pretend it’s anything else.

Join us next time!

RCTB: Charlie Sykes

May 9, 2026 at 2 PM ET

Previously on Stew On This:

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The Story We Wanted to Believe

For about a decade now, much of the pro-democracy coalition has accepted a story that, on quiet reflection, none of us has ever been quite sure we believe. The story told most insistently by The Bulwark, The Dispatch, and the various Never-Trump remainder firms now runs roughly as follows: th…

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The dominant take on James Comey’s second indictment is that it’s laughable. Unprofessional. Beneath the dignity of serious law. A former FBI director charged with threatening the president’s life via a beach photo via seashells is the kind of thing that writes its own punchline. And the commentariat, with characteristic efficiency, has obliged. Legal a…

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The Oil Change

I was getting my oil changed when I first heard it.

A woman was talking to the mechanic about the shooting the night before, on Saturday, April 25th. The White House Correspondents’ Dinner at the Washington Hilton, where a gunman named Cole Tomas Allen had stormed a security checkpoint, fired at least one…

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Pundit Talk

On a recent episode of his podcast, with his brother Buckley Carlson as a guest, Tucker Carlson apologized for supporting Trump. He’s now publicly against the sitting president over the Iran war policy an…

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There are four dark truths about the American public that the approval-rating industrial complex cannot metabolize without dismantling itself:

The first is that American politics has always been exp…

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I’ve been a little sour on the pundit optimism around the 2026 midterms. Maybe it’s because we’ve been through this rodeo before, the Democratic House being pushed to impeach the president the last time they won a midterm in the Trump era, watching that constitutional mechanism rendered useless by the partisanship o…

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Author’s Note: This is a compilation of my thoughts, notes, and reading as I have debated that conservatism in the American context was inevitably going to produce Trumpism, even when a significant portion of the pro-democracy coalition seems to argue against that notion, despite the historical throughlines.

I. …

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