The Dispatch Podcast: “Why Democrats Failed on Immigration” | Roundtable

Date: December 19, 2025
Host: Steve Hayes
Guests: Jonah Goldberg, Kevin Williamson, Grayson Loeb

Overview

This lively roundtable session on The Dispatch Podcast centers on an in-depth post-mortem of the Biden administration’s immigration policy failures, driven by a recent New York Times investigative piece. The panel also tackles the fallout from the unprecedented interviews given by Trump’s White House Chief of Staff Susie Wiles, before finishing on a lighter note with a discussion about memorable road trips. Throughout, the conversation blends sharp policy insight, on-the-ground reporting, and trademark Dispatch skepticism, focusing on the interplay between media coverage, political incentives, and policy outcomes.

Key Discussion Points & Insights

1. Media Critique: The New York Times Immigration Exposé

• Initial Framing: Steve Hayes introduces the NYT piece as an “extraordinary investigative” look-back revealing the administration entered office with no immigration plan, failed to heed early internal warnings, and eventually presided over an acknowledged “disastrous” four years.
  (See: [00:00–04:05])
• Media Hindsight vs. Real-Time Reporting:
  • Williamson: Notes the Times “can do history, but not journalism” when it comes to Democratic failures; the reporting comes “after the fact” when officials are more willing to talk. ([04:05])
  • Hayes: Defends this as a natural limitation—sources are reluctant to criticize an active administration on the record. “It’s a lot easier to get people to talk when they’re looking back at a policy.” ([04:51])

2. The Biden Administration’s Fundamental Strategic Failures

• No Clear Policy Goals:
  • Williamson: “The Biden administration didn’t have a strategy because he didn’t have a goal.” The team failed to understand or engage with the true diversity of Latino communities or formulate a coherent response to immigration pressures. ([06:07])
  • On misreading the Latino vote: “People of Latino backgrounds do not have especially permissive views of immigration… It’s foolish to lump all Spanish-speaking people into a single political category.” ([07:39])
• Kamala Harris’ Ineffectiveness: Criticized for her “California-based” perspective and ineffectiveness when notionally in charge of the issue. ([09:25])

Notable Quote:

“They didn’t know what they wanted, except they knew they had a political outcome they wanted and they went about pursuing that political outcome in a way that was incompetent and ignorant…”
—Kevin Williamson ([08:46])

3. Politics Over Policy: Why the Crisis Escalated

• Jonah Goldberg: Observes that to the extent decisions were made, “those decisions at almost all times were driven by political considerations more than policy outcomes.” ([11:53])
  • Biden’s aversion to the topic compared to his discomfort with abortion “because he knows it’s not the position he wants to have and would rather not talk about it.” ([11:53])
  • Staff “emissaries from the groups” (activist organization types) further muddied policymaking, reducing nuanced demographics into DEI buzzwords and pressuring Biden to follow shallow, symbolic gestures. ([14:03])
• Hayes: Points out that both parties have misunderstood or mishandled the issue, citing the 2012 RNC “autopsy” and Trump’s different political instincts. ([17:27])

Notable Quote:

“When you do public policy as allegories where each person in the room represents tens of millions of people, you’re going to get policy wrong and you’re going to get politics wrong.”
—Jonah Goldberg ([16:40])

4. On-the-Ground: Reporting from the Border

• Grayson Loeb: Fresh from Yuma, Arizona, underlines the practical fallout—a small city overwhelmed by daily crossings—making the crisis “real” and hard to ignore for local officials, regardless of their politics. Resources were stretched to the breaking point, illustrating the disconnect between federal inaction and local needs. ([19:18])
  • Humanitarian crises included lack of hospital car seats for newborns, fire departments rescuing migrants, and overwhelmed emergency response systems. ([21:19])

Notable Quote:

“The story is that there’s no story. This was one of the hotspots... now it’s like five arrests a day, which is basically nothing. But that’s the notable fact—such a contrast.”
—Grayson Loeb ([21:45])

5. Turning Point: Texas Busing Stunt and Political Optics

• Event: Texas Governor Greg Abbott’s decision to bus migrants to Democratic cities made the crisis inescapable for party leadership nationwide, shifting the Biden administration’s posture.
  • Hayes: While he “didn’t love it” as it used people as props, it was “effective, and in pretty short order.” ([24:30])
  • Williamson: Calls it an “obviously effective stunt,” which forcibly demonstrated that “this is a story about U.S. policy”—not just external factors. Suddenly, the problem “had faces and needs in New York, not just in Yuma.” ([26:23])
  • Goldberg: Argues the move forced Democratic strongholds to confront the realities local border communities had been facing for years. ([33:42])
• Gradual Policy Shift Too Late:
  • As the crisis grew harder to deny, the Biden administration acknowledged problems, made policy changes, and numbers fell—but “too late to change the sense of the country, certainly heading into a presidential election year.” ([35:02])

Notable Quote:

“It did make a difference. Again, it was a stunt... but probably useful… for people in the rest of the country to understand in more visible, human terms just what this issue really looks like.”
—Kevin Williamson ([27:16])

6. How Did Flows Stop? Policy or Rhetoric?

• Late Biden Clampdown: At the end of 2024, Biden’s team “really start[ed] to clamp down on asylum,” reducing the number but not eliminating crossings.
• Trump’s Rhetoric/Policy: Trump’s ascension and “even stricter” policies (virtually zero asylum/humanitarian access) led to “a drop from 70,000 people one month to 10,000 people the next month.”
  • Loeb and others argue this sharp drop is mainly attributable to the “message effect”—Trump’s aggressive deterrence rhetoric, amplified ironically by Democratic mayors and governors decrying his policies, may have been even more effective as a deterrent. ([36:31])
  • The episode ends with the recognition that policy, enforcement, and the rhetorical signal from the White House all play a role, but perceptions (and who’s in charge) can rapidly amplify or suppress flows.

Notable Quote:

“In terms of—we were on a downward trajectory… then it really just fell off a cliff to effectively like close to nothing. A lot of that can be attributed to the messaging.”
—Grayson Loeb ([37:43])

Notable Quotes & Memorable Moments

| Timestamp | Quote & Context | Speaker | |------------|-----------------|---------| | 08:46 | “They didn’t know what they wanted, except they knew they had a political outcome they wanted and they went about pursuing that political outcome in a way that was incompetent and ignorant...” | Kevin Williamson | | 11:53 | “Those decisions at almost all times were driven by political considerations more than policy outcomes, desired policy outcomes.” | Jonah Goldberg | | 16:40 | “When you do public policy as allegories where each person in the room represents tens of millions of people, you’re going to get policy wrong and you’re going to get politics wrong.” | Jonah Goldberg | | 21:45 | “The story is that there’s no story. This was one of the hotspots... now it’s like five arrests a day, which is basically nothing. But that’s the notable fact—such a contrast.” | Grayson Loeb | | 27:16 | “It did make a difference. Again, it was a stunt... but probably useful… for people in the rest of the country to understand in more visible, human terms just what this issue really looks like.” | Kevin Williamson | | 36:17 | “One of my favorite quotes from that time was Vice President Harris saying, I believe if you come, you will be stopped at the border, not like, ‘if you come, you will be stopped.’” | Grayson Loeb | | 37:43 | “It really just fell off a cliff to effectively like close to nothing. A lot of that can be attributed to the messaging.” | Grayson Loeb |

Segment Timestamps

• Immigration Policy Failure: [00:00–39:31]
  • Media criticism, policy failure, political calculations, border reporting, Texas busing, trajectory of migrant flows.
• Susie Wiles Interviews – White House Chief of Staff: [41:24–63:48]
  • Vanity Fair interviews; reveals legal exposure, score-settling, why leakers leak (reputation management), how White House chiefs differ.
  • Notable: Susie Wiles admits U.S. objective in Venezuela is regime change; breaks with White House line.
  • Trump’s advisers rally to Wiles despite her on-record criticisms—a function of her unique relationship with Trump (“She never tries to restrain him.”)
• Road Trip Stories (“Not Worth Your Time”): [66:05–78:32]
  • Panelists reminisce about memorable road trips and favorite fast-food stops on the road.
  • Humorous anecdotes about train journeys and sleeping in cars during college travels.

Language, Tone & Style

Throughout, the roundtable is sharp, wry, and never far from self-deprecating humor. The tone is slightly skeptical but empathetic, blending policy wonkery with real-world reporting and irreverent asides.

• Kevin Williamson is blunt and data-driven, rarely mincing words regarding the administration’s ignorance or the media’s delay in telling the full story.
• Jonah Goldberg supplies historical and conceptual context, often relating current policy to broader phenomena—group identity politics, Beltway bubble thinking, and the perils of ideological staff.
• Grayson Loeb contributes recent border reporting and offers granular, practical anecdotes to counter Washington abstraction.

Conclusion

This episode dissects the Democratic failure on immigration policy, laying the blame at the feet of diffuse leadership, misunderstood constituencies, timid media, and ultimately, politics triumphant over policy. The subsequent sharp, candid segment on Susie Wiles’s jaw-dropping interviews adds a window into the contrasts between Trump’s and Biden’s advisory universes. The show rounds out with road trip banter, but the substance of the immigration discussion—backed by New York Times reporting, fieldwork, and historical perspective—serves as both diagnosis and warning for political actors and journalists alike.