The Gist: “Trump’s Long Game and Miles Taylor’s Warning”

Date: August 23, 2025
Host: Mike Pesca
Guest: Miles Taylor (fmr. DHS Chief of Staff, author, once “Anonymous”)

Overview

In this episode, Mike Pesca explores the enduring risks posed by a potential second Trump presidency. He lays out his immediate concerns about Trump’s policy goals which stretch well beyond a single term—and the threats inherent if democracy’s safeguards fail. Most of the episode features an in-depth conversation with Miles Taylor, the former Homeland Security official who famously authored the 2018 “Anonymous” op-ed and whose new book, Blowback: A Warning to Save Democracy from the Next Trump, expands on the internal dangers faced during Trump’s first term and warns of even more calculated efforts should Trump return to the White House.

Key Discussion Points & Insights

Mike Pesca’s Opening Reflections on Trump’s "Long Game"

Timestamps: 03:50–09:47

• Pesca unpacks his unease about Trump’s second-term ambitions:
  • Many Trump policies, especially around tariffs, civil service purges, and international alliances (like NATO), are designed for long-term impact—years after a single term is over.
  • Trump’s strategy: “He’s not the sort of person … to say my successor will carry my mantle and that will be fine with me because I care about my legacy ... Not that kind of guy.” (05:55)
  • Pesca believes there’s a “decent chance” (35-40%) that Trump is devising ways for his agenda to outlive his time in office—through successors, refusal to accept future election results, or even rerunning for office.
  • Worries about fair and honest elections in 2026 midterms and 2028 presidential cycle: “If we don’t have those actual elections … it’s a disaster. We need to take that extremely seriously.” (09:37)

Interview with Miles Taylor

Timestamps: 10:48–33:00

The “Anonymous” Op-Ed and the Risks of Anonymity

Timestamps: 12:19–17:09

• Taylor reflects on choosing anonymity to draw attention to the internal resistance and provoke real debate within the administration, citing the Federalist Papers as an inspiration.
• Quote:

  “I naively thought I could kick start that kind of conversation by writing this piece from within the administration anonymously.” (14:40 – Taylor)

• Taylor admits anonymity was a double-edged sword:
  • It fueled Trump’s paranoia about the “deep state.”
  • Stephanie Grisham (Trump’s comms director) told him Trump would search rooms, asking, “Do you know who Anonymous is?” (16:00)
  • This intensified Trump’s suspicion and conspiracy thinking, but also helped publicize concerns about his fitness for office.

On the “Axis of Adults” and Internal Guardrails

Timestamps: 17:09–20:23

• Pesca references Tim Wu’s NYT op-ed about informal institutional norms saving the Republic.
• Taylor’s hard-earned conclusion:

  “That thesis was completely bogus ... Trump systematically identified and eliminated those people.” (17:46 – Taylor)

• He believes “the American people should not depend on unelected bureaucrats; that’s not their role. It’s the role of voters.”
• Taylor regrets not unmasking himself sooner, as doing so empowered others to speak out.

Moral Choices and Regrets inside the Trump Administration

Timestamps: 22:58–24:41

• Taylor recounts the “moral choose your own adventure” faced by insiders: oppose, stay, quit, speak out, or not.
• A revealing anecdote: When Taylor finally told John Kelly (former Chief of Staff) he was “Anonymous,” Kelly replied:

  “I’m so f***ing proud of you and thank you.” (20:33)

• On broader reflection: “I'm unafraid at this point in my life to be a cautionary tale.” (23:06)
  He labels the notion of re-electing Trump as “civic suicidal ideation.”

Second-Term Dangers: Staff, Civil Service, and Autocracy

Timestamps: 24:41–30:21

• Pesca asks how Trump could staff his government with loyalists without Senate approval.
• Taylor notes there is a plan to circumvent the Senate:
  • Trump could install acting officials, challenge limits in court, and simply ignore rulings if uncooperative.
  • Quote:

    "They’re prepared to go to war with the courts because they know the courts cannot enforce these decisions ..." (25:00)

• Trump and allies have built legal frameworks (e.g., “Schedule F”) for mass purges of civil servants, further politicizing nonpartisan federal jobs.
• Taylor details attempts to use federal aid as political leverage, especially to punish Democratic states:

  “He was always looking for some kind of leverage, especially if it was in a blue state ... He asked DHS and FEMA to withhold the aid.” (29:00)

Why the Warning Might Fail—and the Prospect of a Worse Successor

Timestamps: 30:21–32:42

• Taylor points out: Trump’s allies are openly promising, not warning, about these plans.

  “The things that I’m warning about in Blowback are the things they are openly claiming they're going to do...” (31:23)

• His hope is for a “coalition of the sane"—moderate Republicans, independents, and centrists who can reject this path before it’s too late.
• Taylor worries Trump’s actions have “tilled the fertile soil for someone worse than him,” enabling future copycats.

Notable Moments & Quotes

• Pesca’s skepticism about Trumpism as “conservatism”:

  “Donald Trump is not a conservative ... he wants a government and a presidency that has so much power … That’s what we call autocracy.” (24:00 – Taylor)

• Taylor on regret and warning the country:

  “I probably made every wrong moral choice along that line and eventually got to the right choices ... I’m unafraid at this point in my life to be a cautionary tale ...” (23:06)

• The chilling prospect of ignored checks and balances:

  “What authority does the Supreme Court have to enforce that decision? There is none.” (25:22 – Taylor)

Timestamps for Major Segments

• 03:50–09:47: Pesca’s analysis of Trump’s “long-term” policy horizon and electoral worries
• 10:48–17:09: Taylor’s account of anonymity, resistance, and “deep state” paranoia
• 17:09–20:23: Internal administration “guardrails” and the myth of bureaucratic protection
• 20:23–24:41: Taylor’s coming-out, John Kelly’s response, and moral quandaries
• 24:41–30:21: Threats of Senate circumvention and mass politicization of the civil service
• 30:21–32:42: Messaging wars: warning vs. promise, the risk of “Trumpism” outliving Trump

Tone & Takeaways

• The conversation is candid, often self-critical, and marked by a palpable sense of urgency and responsibility.
• Taylor repeatedly emphasizes systemic risks and moral choices, while Pesca tempers the discussion with his trademark skepticism and wordplay.
• Both urge listeners not to depend on internal “heroes” but to take civic action before democratic norms are pushed past a point of no return.

For those who haven't listened:
This episode offers an insider’s unvarnished view of how fragile America’s institutional norms proved under Trump, why a second term (or a future copycat) could be even more dangerous, and what citizens must do to protect what’s left of U.S. democracy.