Countdown with Keith Olbermann

Episode: THEY USED SIGNAL TO BYPASS TRUMP. THEY KNOW HE'S GOING CRAZY

Date: March 27, 2025

Overview

In this episode, Keith Olbermann dives into a bombshell revelation: key members of the Trump administration used the encrypted messaging app Signal to communicate sensitive national security plans—specifically, discussions about bombing Yemen—purposefully to exclude Donald Trump from the conversations. Olbermann argues that Trump's own cabinet no longer trusts his judgment or mental fitness, so they developed a workaround to conduct policy discussions without his involvement. The episode details the legal and political implications of this, lampooning the key figures involved, and drawing comparisons to past governmental miscommunications. Classic Olbermann snark, political analysis, and some personal anecdotes on governmental incompetence are woven throughout.

Key Discussion Points & Insights

1. The Underlying Scandal: Cabinet Members Bypassing Trump

• Revelation: Trump’s national security and defense team deliberately organized secure communications on Signal to keep Trump in the dark about war planning, especially relating to Yemen.
  • Olbermann’s summary: “They are cutting Trump out. That is the only and the inescapable conclusion to all this.” (04:52)
  • Motivation was not secrecy from Democrats or investigators, but from Trump himself because of fears about his stability and unpredictability.
• Espionage Law Reference:
  Olbermann points to 18 US Code 793 as potentially applying to these officials (“gathering, transmitting or losing defense information. Paragraph F.”) and details its wide applicability—even if the information isn’t classified. (06:47)

2. The Players and Their Missteps

• Key officials involved: Mike Waltz (National Security Advisor), Tulsi Gabbard (Director of National Intelligence), Pete Hegseth (Secretary of Defense), with cameo idiocy from JD Vance and others.
  • Highlights Waltz’s awkward explanations for why journalist Jeffrey Goldberg appeared in the signal chat.
  • Gabbard’s carelessness: Gabbard’s phone and Signal profile details were easily found online, as reported by Der Spiegel. (19:32)
  • Per Olbermann, many participants acted with stunning incompetence: “Three of the biggest idiots in the history of this country…” (04:31)
• Notable quote regarding Trump’s grasp:
  “He had no idea what the messaging scandal was, and he had no idea who Jeffrey Goldberg was, and he could barely remember what the Atlantic was long enough to take a really low energy dig at its circulation numbers. Trump is going potty and his cabinet knows it.” (05:43)
• Olbermann’s characterizations:
  He repeatedly calls the cast of characters “idiots,” often listing them rapid-fire for comedic effect.
  E.g., “Mike Waltz is an idiot. JD Vance is an idiot. Pete Hegseth is an idiot... Tulsi Gabbard, two idiots...” (27:44)

3. Legal & Security Implications

• Espionage Risks:
  These officials could theoretically be prosecuted under Espionage Act for transmitting defense info on an app after being warned not to. But political reality (the Attorney General being loyal to Trump) makes this unlikely.
  • “To be guilty of espionage, you have to be charged with espionage. And the person who would charge the other people on the list with espionage is probably the most subservient of Trump’s slaves, his Attorney General.” (11:10)
  • Still, the 10-year statute of limitations lingers over these actors.
• Security Breaches:
  The app (Signal) was formally prohibited by the NSA for sensitive communications just a month prior, yet officials ignored this.
  • “The National Security Agency put out a memo last month specifically saying: do not use Signal. It’s vulnerable... This chat, this edition of Signal Gate came after that warning.” (22:28)
• Contradictory Arguments:
  Officials try to claim the chat wasn’t about classified info, though discussions touched on targeting and war timelines for Yemen. - “The director of no Intelligence [Gabbard] says there was a discussion around targets. That would be war plans. Levitt said there were no war plans. Levitt lied.” (25:39–25:57)
  • Olbermann notes the hypocrisy given their attacks on Hillary Clinton for analogous infractions.

4. The Goldberg Mystery: Media Access and Paranoia

• Jeffrey Goldberg, Editor of The Atlantic, ended up on the Signal chat. Reasons were murky.
  • Olbermann suspects this is because Waltz or another official had him in their phone as a semi-regular contact, possibly from older, more bipartisan days at the Pentagon.
  • Paranoia spreads: “Trump’s chief concern during multiple conversations with Waltz has been why his NSA would have Goldberg’s number in the first place.” (citing Politico, 10:31)
  • Olbermann’s Occam’s razor: “Goldberg was in Waltz’s phone because Waltz put him there.” (16:30)

5. Anatomy of the Leaks: International Fallout

• German newspaper Der Spiegel easily tracks down the officials' phone numbers, emails, and even their app accounts from public breaches:
  • “Der Spiegel reports: Reporters were able to find mobile phone numbers, email addresses, and even some passwords belonging to the top officials... those affected include Waltz, Gabbard, and Hegseth.” (19:32)
  • He lampoons the data security practices of U.S. intelligence officials using as inspiration Gabbard’s leaky Signal profile.
  • “Just when you think human speech has become advanced enough to describe how dumb Tulsi Gabbard is. The DNI, the Director of National Intelligence, has a Signal profile connected to a phone number that is available on the Internet.” (20:24)

6. What the Leaked Chat Revealed: Who’s Really in Charge?

• Key content of the Signal chat:
  • JD Vance expresses doubts about bombing Yemen, proposes delay owing to lack of public understanding, risk to oil markets, and inconsistencies with Trump’s public message.
  • Joe Kent (Counterterrorism Center nominee): “There is nothing time sensitive driving the timeline. We'll have the exact same options in a month.” (29:01)
  • SM (unidentified): Rehashes the President’s order but prioritizes extracting economic concessions from allies.
  • Key insight: These officials are having a genuine, reasoned debate outside the President’s view, fearing his instability.
    • “I mean, read those texts. The bully boy in eyeliner, that’s Vance in public, threatening and swearing and blustering. The guy in the text seems to think about things.” (06:41)
• Olbermann's conclusion: “The point of this is you have a president whose own people think he is now a complete Phoebe, that he cannot function, that he cannot be trusted, that he cannot be trusted not to do something at least disastrously stupid...” (13:40)

7. Historical Parallels and Incompetence in Government Communications

• Olbermann relates personal and historical anecdotes of communication breakdowns in government:
  • Civil War: Robert E. Lee’s Special Order 191, a lost invasion plan found by a Union soldier.
  • Bush Administration: The White House’s hilarious inability to spell Olbermann’s name correctly and resultant misdirected emails, highlighting bureaucratic incompetence.
    • “Put an email in front of an administration staffer, any administration, any century and they would screw it up. Put a phone call… and they would screw it up. Put literally a handwritten note… and they did screw it up.” (39:50)
  • Personal story with Joe Wilson: Olbermann recounts the White House attempt to plant talking points with him before an interview with former Ambassador Joseph Wilson, which backfired spectacularly.

8. "Worst Persons in the World" Segment (starts 53:39)

• Bronze: Stephanie Borowitz, a Pennsylvania legislator, for bragging about a perfect “John Birch Society” score.
• Runner Up: Steve Bannon, whose increasingly self-censored rants make for “a show without the violent threats.”
• Winner: Bill Maher, mocked for pal-ing around with Kid Rock, wanting to meet Trump at the White House, and for Olbermann’s long, comic history of knowing—but not liking—Maher back to their days at Cornell.

Memorable Quotes & Moments

• On Trump being cut out:
  “There was a workaround around Trump. They are cutting Trump out. That is the only and the inescapable conclusion to all this.” (04:52)

• On cabinet's judgment of Trump:
  “The only part of the job he's putting any effort into anymore is the blah blah blah speech part.” (05:28)

• On espionage law:
  “It does not have to be classified information... It only has to be defense information that's in the code. Transmitting or losing defense information.” (12:54)

• On technological cluelessness:
  “They are convening on Signal, which might as well be an app you get free with the purchase of a lot of porn because there is no chance Trump has any idea how it works.” (05:08)

• On administrative stupidity as democracy's greatest bulwark:
  “For the one millionth time in this series alone, the democracy is preserved less by our exertions to save it than it is by the stupidity of those who seek to destroy it.” (27:59)

• On the Biden security clearance double standard:
  “The context of all this was the big show they made last week of Trump removing security clearances of the Bidens and everybody else he doesn’t like because nominally they can’t be trusted with secret information. … We have to keep that for Tulsi Gabbard to give away.” (26:47)

Timestamps for Important Segments

| Segment | Timestamp | |--------------------------------------------------|---------------| | Olbermann’s opening thesis: cabinet vs. Trump | 04:15–06:30 | | Espionage Act law explanation | 06:47–12:50 | | Signal leak details & officials' incompetence | 19:32–22:50 | | Detailed legal contradictions & hypocrisy | 23:37–27:35 | | Signal chat content analysis | 28:50–30:50 | | Personal anecdotes on government incompetence | 38:30–50:30 | | “Worst Persons in the World” segment | 53:39–61:00 |

Notable Quotes (with Attribution and Timestamp)

• “He had no idea what the messaging scandal was... Trump is going potty and his cabinet knows it.”
  — Keith Olbermann, 05:43

• “There is at least one ghost mechanism in place to allow Trump’s cabinet members to try to get something done without destroying the world yet.”
  — Keith Olbermann, 13:01

• “Goldberg was in Waltz’s phone because Waltz put him there.”
  — Keith Olbermann, 16:30

• “The director of no Intelligence says there was a discussion around targets. That would be war plans. Levitt said there were no war plans. Levitt lied.”
  — Keith Olbermann, 25:39–25:57

• “Just when you think human speech has become advanced enough to describe how dumb Tulsi Gabbard is. The dni, the Director of National Intelligence, has a signal profile connected to a phone number that is available on the Internet.”
  — Keith Olbermann, 20:24

Tone & Style

Olbermann is blistering, sardonic, and hyperbolic—freely calling high-ranking officials “idiots,” musing about whether the saving grace of democracy is the sheer incompetence of its would-be saboteurs, and liberally referencing everything from Sunset Boulevard to his own career blunders. Long detours into historical and media-industry anecdotes are used to lampoon perennial governmental dysfunction.

Summary Takeaways

• Trump’s own cabinet intentionally excluded him from major national security conversations due to a perceived loss of his mental faculties.
• Their use of insecure technology (Signal), against explicit security advice, now exposes them to espionage charges—though prosecution is unlikely barring a political sea change.
• The scandal highlights both how little faith senior officials have in Trump, and the ongoing, historic inability of governmental staff to securely or competently communicate.
• Olbermann concludes the survival of democracy may depend less on valiant defenders and more on the idiocy of those trying to undermine it.

For more detailed news, Olbermann’s full historic anecdotes, and sparkling asides—listen to the full episode.