Deadline: White House – “Bad cop”
Date: December 9, 2025
Host: Nicolle Wallace (MS NOW)
Guests: Miles Taylor, Shelby Holliday, Lt. Gen. Mark Hertling, Carol Leonnig, Andrew Weissman
Overview
Today's episode dives deeply into the Trump administration’s controversial and potentially illegal military strikes on suspected drug trafficking boats in the Caribbean, focusing on the second, deadly “double tap” strike that killed unarmed shipwreck survivors. The episode also investigates the ensuing congressional oversight, allegations of coverup, fallout within the Department of Defense, and implications for the rule of law. Later segments turn to the Trump Justice Department’s repeated efforts to indict New York AG Letitia James for mortgage fraud—a crime Trump himself is accused of—and reactions to new, restrictive immigration enforcement policies.
Key Discussion Points & Insights
1. The Boat Strikes Controversy
Congressional Scrutiny and Lack of Transparency
- 00:01:08 Nicolle Wallace opens with mounting bipartisan demands for transparency over recent U.S. military strikes on boats in the Caribbean. The annual defense policy bill would require release of unedited strike video and withhold part of Defense Secretary Pete Hegseth’s travel budget if he doesn't comply.
- The second strike, in which survivors of an initial bombing—unarmed men adrift, possibly signaling surrender—were killed, is especially contentious. Eyewitness descriptions paint the incident as brutal and senseless.
“The harrowing, frankly horrific nature of what's being described ... is one reason why the questions around what exactly the Trump administration is doing seem to be multiplying by the day.”
— Nicolle Wallace (01:50)
- Admiral Alvin Holsey, outgoing head of US military ops in the Caribbean, was reportedly pushed to resign by Hegseth after expressing legal qualms.
Trump’s Attitude Toward Rules of War
- 05:20 Miles Taylor reveals, from his own White House experience, that disregard for the laws of war isn’t new for Trump or his advisors:
- In 2018, Stephen Miller questioned if the U.S. could lawfully bomb unarmed civilians on boats. Taylor and other officials called this “obviously illegal.”
- Trump frequently complained about the “rules of engagement,” seeing them as a hindrance rather than a safeguard.
“He was frustrated that he heard [rules of engagement] so much in the first term. He saw it as a restriction. He doesn't want to abide by those rules this time.”
— Miles Taylor (06:19)
Motivations and Effectiveness
- When Wallace presses Taylor on Trump’s motivations, Taylor argues it’s about projecting power, comparing it to mob tactics for intimidation.
- Operationally, targeting low-level traffickers by lethal means is counterproductive; intel from arrests is lost.
"He's not helping this case, he's hurting this case. And in the meantime, to me, very clearly is breaking the law."
— Miles Taylor (07:50)
- Taylor and Wallace highlight the illogical focus on cocaine boats (not fentanyl) and point out that some Trump allies (e.g., Laura Loomer) are breaking ranks, saying the policy makes no sense even on its own terms.
2. Legality, Military Practice, and International Fallout
Military Expert Analysis
- 11:16 Gen. Mark Hertling bluntly states there’s no justification for the second strike. He draws historical parallels to Abu Ghraib and underscores the operational folly of destroying evidence needed to dismantle drug networks.
"You don't treat prisoners the way they were treated at Abu Ghraib, the same way you don't treat those who were narco-terrorists ... give the description to an immediate death sentence."
— Gen. Mark Hertling (11:22)
- Hertling warns that these actions, and the lack of adherence to the rules of engagement, risk alienating key U.S. allies in Latin America and Europe.
“This is the kind of things that will take our allies and push them away from us... so we're losing more than just the argument on illegality.”
— Gen. Mark Hertling (13:32)
3. Video Release Debate and GOP Fracture
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14:10 Wallace notes that even Senate Republicans (Josh Hawley, Lindsey Graham) now call for release of the second strike video, undermining the administration’s previous partisan firewall.
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Shelby Holliday observes that the Pentagon has already released 22 strike videos; withholding this one, supposedly for “sources and methods” reasons, appears inconsistent and likely a pretext.
"It's a bit of a stretch... you can't release 22 videos and then not this other one."
— Shelby Holliday (14:42)
- There’s disagreement over what the video actually shows:
- Admin supporters argue the men could have retrieved the drugs and continued their mission.
- Critics, including some who’ve seen the footage, dispute that and emphasize the necessity of public transparency.
"If the Secretary is so proud of releasing, like you just said, 20 some odd videos of the strike, then he should be proud of releasing ... the second strike. Because there's no difference ..."
— Gen. Mark Hertling (17:28)
4. Administrative Dysfunction & Chain-of-Command Breakdown
- Shelby Holliday reports (23:30) on deep tensions between Hegseth and Admiral Halsey, becoming more acute as the boat campaign escalated, including orders and special ops actions carried out without Halsey's knowledge or consent.
- Hertling explains the vital importance of coordination between commands and the damage caused by undermining combatant commanders with regional expertise.
“When you have someone coming in with a carrier strike group and a bunch of special operators, you would think they would pay attention to some of his advice. Sometimes that doesn't happen.”
— Gen. Mark Hertling (27:17)
5. Trump DOJ’s Pursuit of AG Letitia James (Mortgage Fraud)
Selective Prosecution Exposed
- Wallace (29:08) lays out the Justice Department’s repeated — and thus far unsuccessful — attempts to indict NY AG Letitia James for allegedly claiming multiple residences on mortgages, even as new reporting by ProPublica reveals Trump himself did the same thing:
- Trump claimed two adjacent Palm Beach properties as his principal residence when he lived in neither, “exactly the sort of scenario his administration has pointed to as evidence of fraud.”
"It tells you that it's like ... A prosecution for enemies. But with respect to Paul Manafort and Donald Trump, it should all be absolved."
— Andrew Weissman (34:30)
- Carol Leonnig confirms the DOJ has never previously re-tried a case three times after two grand jury failures—calling it an extraordinary example of vindictive prosecution.
Erosion of DOJ Integrity
- Carol Leonnig and Andrew Weissman discuss the demoralization among career DOJ officials, who have quit or been pressured out, and the lack of a clear ethical “line” for current DOJ leaders like Todd Blanche and Pam Bondi.
“If you are the number one and the number two at the Department of Justice and this is going on and you privately know and understand that it is wrong and it is not a righteous prosecution, you need to not only privately, as Carol said, stand up and say, this is wrong. But you have to have the moral fiber to be willing to leave and say, I cannot be a part of this.”
— Andrew Weissman (42:23)
6. Immigration Policy and State Pushback
- Illinois Gov. J.B. Pritzker (44:09) signs new law restricting federal immigration enforcement at sensitive locations, following intense federal crackdowns in Chicago and other cities.
- New York lawmakers are preparing similar legislation; Wallace calls Trump’s approach “inhumane depravity.”
Notable Quotes & Timestamps
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On the strike video:
“The harrowing, frankly horrific nature of what's being described ... is one reason why the questions ... seem to be multiplying by the day.”
— Nicole Wallace (01:50) -
On Trump's disregard for the laws of war:
“He saw [rules of engagement] as a restriction. ... even if that means committing murder on the high seas.”
— Miles Taylor (06:19) -
On operational logic:
"If you want to crack the cartels ... you need to roll up and arrest these guys ... [Trump]’s destroying the evidence ..."
— Miles Taylor (07:52) -
On legality and moral loss:
"You don't treat prisoners the way they were treated at Abu Ghraib, the same way you don't treat those who were narco-terrorists ... give the description to an immediate death sentence."
— Gen. Mark Hertling (11:22) -
On DOJ double standards:
"It tells you that it's like ... a prosecution for enemies. But with respect to Paul Manafort and Donald Trump, it should all be absolved."
— Andrew Weissman (34:30) -
On DOJ leadership’s lack of principle:
"If you are the number one and two at DOJ ... and you privately know ... it is not a righteous prosecution, you need to ... leave and say, I cannot be a part of this."
— Andrew Weissman (42:23)
Section Timestamps
- Trump boat strikes: context and congressional action: 01:08 - 05:20
- Rules of engagement and Trump's views: 05:20 - 09:30
- Debate over motives/logic of strikes: 07:23 - 09:30
- Military legality and global repercussions: 10:51 - 13:52
- Republican splits on video release: 13:52 - 15:57
- Video evidence and operational details: 15:21 - 17:04
- Pattern of coverup—comparison to Epstein: 18:52 - 20:29
- Breakdown of military chain of command: 23:30 - 25:08
- DOJ and Letitia James mortgage fraud: 29:08 - 35:23
- Legal analysis of selective prosecutions: 35:23 - 38:05
- Department morale and leadership’s line: 40:00 - 43:46
- Immigration enforcement state resistance: 44:09 - 44:55
Memorable Moments
- Exposé of the second boat strike, including vivid, disturbing witness descriptions.
- Rare break in Republican ranks, with top GOP senators calling for video release.
- Blunt military analysis comparing strike’s fallout to Abu Ghraib and warning of lost alliances.
- Legal experts detailing the Trump DOJ’s unprecedented “selective and vindictive” prosecutorial crusade against AG Letitia James—even as Trump engaged in the same alleged fraud.
- Andrew Weissman’s forceful indictment of DOJ leaders who privately object but refuse to resign or act.
Summary by Section, Notable Quotes, and Timestamps prepared for listeners seeking a comprehensive, engaging, and clear understanding of the “Bad cop” episode of Deadline: White House.