The Don Lemon Show
The Don Lemon Show
June 5, 2026

Lemon LIVE at 5 | Holy Sh*t, Donald Trump Had A Bad Week!

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Quick Read

Don Lemon and Anthony Scaramucci dissect a 'colossally bad week' for Donald Trump, highlighting his political setbacks and discussing strategies for the Democratic party to leverage the shifting political landscape.
Trump faced multiple legal and legislative defeats, including a 'slush fund' cancellation and a bipartisan rebuke on war powers.
His low approval ratings and lack of credible allies indicate a weakening political position.
Democrats should prioritize winning elections by embracing a 'big tent' strategy over 'purity tests' to defeat Trumpism.

Summary

Don Lemon opens the show by detailing a series of significant setbacks for Donald Trump, including the official declaration of his 'slush fund' as dead, the bipartisan passage of the War Powers Resolutions Act, the removal of his name from the Kennedy Center, and a federal court ruling against his transgender military ban. Anthony Scaramucci joins to corroborate the 'bad week' narrative, interpreting Trump's low approval ratings and lack of credible cabinet voices as signs of the 'slow decline of Trumpism.' The conversation expands into a discussion on political strategy, emphasizing the need for Democrats to focus on winning elections by appealing to independents and letting go of minor 'culture war' battles, rather than imposing strict 'purity tests' on potential allies. Personal anecdotes from callers reinforce the idea that engagement and open dialogue can lead to changing hearts and minds, even among those with opposing views.
This episode offers a critical perspective on the political vulnerabilities of Donald Trump, providing a detailed account of his recent legal and legislative defeats. It also delves into a crucial debate about effective political strategy for the Democratic party, suggesting that a more pragmatic, 'big tent' approach focused on electoral victory, rather than ideological purity, is essential to counter Trumpism. The personal stories shared by callers underscore the power of dialogue and empathy in bridging divides, offering a human dimension to the political discourse.

Takeaways

  • Donald Trump experienced a 'very bad week' marked by multiple legal and legislative defeats.
  • His 'slush fund' for January 6th insurrectionists was declared dead, though lawmakers didn't officially vote to cancel it.
  • Both chambers of Congress passed the War Powers Resolutions Act, telling Trump to end the war in Iran, with bipartisan support.
  • A federal judge ordered Trump's name removed from the Kennedy Center by June 12th.
  • The DC circuit ruled against Trump's transgender military ban for currently enlisted service members.
  • Trump's approval rating stands at 37%, with 61% disapproving of his actions.
  • Anthony Scaramucci views Trump's setbacks as the 'beginning of the slow decline of Trumpism.'
  • Scaramucci suggests that Trump's actions have exposed weaknesses in the system, creating a 'playbook' for future reform-based presidents.
  • The host and guest advocate for a pragmatic political strategy, urging Democrats to focus on winning elections by appealing to independents and choosing battles wisely, rather than adhering to rigid 'purity tests.'
  • Personal stories highlight the importance of open dialogue and maintaining relationships to foster understanding and change, even with those holding opposing views.

Insights

1Trump's 'Slush Fund' Declared Dead

The fund, reportedly created to pay January 6th insurrectionists, was officially declared dead by Todd Blanch, though lawmakers did not formally vote to cancel it. This leaves Trump's personal IRS immunity intact while those he allegedly used are left with nothing.

Todd Blanch testified under oath that they are 'not moving forward with the fund. Period.' This fund was '1.776 million dollar created to pay January 6th insurrectionists and other wrongdoers.'

2Bipartisan Rebuke on War Powers

Both chambers of Congress passed the War Powers Resolutions Act, directing Donald Trump to end the war in Iran. This marks the first time both chambers told a sitting president to stop a war he started without their approval, indicating a crack in his party's unity.

The Senate already passed one. The House passed theirs 215 to 208. Four Republicans crossed over. First time ever, both chambers told a sitting president to stop a war that he started without their approval.

3Removal of Trump's Name from Kennedy Center

A federal judge ordered Donald Trump's name removed from the Kennedy Center by June 12th, stating that its placement was unlawful. This symbolizes a public rejection of his influence.

A federal judge ordered his name removed from the Kennedy Center by June 12th. The law said it never should have been there.

4Federal Ruling Against Transgender Military Ban

The DC circuit ruled two to one against Donald Trump's transgender military ban for currently enlisted service members, further eroding his policy legacy.

The DC circuit ruled two to one against Donald Trump's transgender military ban for currently enlisted service members.

5The Slow Decline of Trumpism

Anthony Scaramucci asserts that Trump's recent string of failures and low approval ratings (37%) signify the beginning of a slow decline for his political movement, as mainstream Republicans start to push back.

Scaramucci states, 'It was a colossally bad week and I would say the beginning it's the beginning of the slow decline of Trumpism.' He notes Trump's 37% approval rating and that 'all [polls] are uniformly bad.'

6Trump's Actions as a Playbook for Reform

Scaramucci suggests that Trump's 'baldfaced' flouting of rules and norms has inadvertently exposed all the weaknesses in the system, creating a clear 'playbook' for a future reform-based president to strengthen democratic institutions.

Trump has been so baldfaced about this, Don, that therein lies the opportunity to push the reform. He's almost exposed all the weaknesses in the system by flouting it.

Bottom Line

The market's superficial strength, driven by AI and power capital spending, masks underlying top-heaviness that could become a problem.

So What?

This suggests a potential economic vulnerability despite current growth, implying that the broader economy might not be as robust as headline numbers suggest, which could impact future political landscapes.

Impact

Investors could look for opportunities in sectors less reliant on AI/power capital or prepare for potential market corrections if this top-heaviness leads to instability. Policymakers should consider broader economic diversification strategies.

The 'grift' and 'pay-for-play' activities, such as contracts for donors to Trump's ballroom and pardons for millions, will eventually face a reckoning, similar to historical figures like Boss Tweed.

So What?

This implies that even seemingly unpunished corruption can eventually lead to accountability, offering a long-term perspective on political ethics and justice. It also suggests that such actions are being meticulously documented.

Impact

For a future reform-based administration, this documentation provides a clear roadmap to implement stronger anti-corruption measures and close loopholes that were exploited, strengthening democratic institutions.

Key Concepts

Culture War Strategy

Anthony Scaramucci advises against winning every point in the 'culture war,' suggesting that focusing on broader political goals and appealing to independents is more effective for long-term victory. Don Lemon echoes this, advocating for strategic alliances even with those who don't share all values, to achieve electoral wins.

Scaffolding (Political Strategy)

Lizzy introduces the educational concept of 'scaffolding' as a political strategy, where complex issues are introduced with umbrella terms to ease people into understanding, taking baby steps towards broader acceptance and change over time. This implies a gradual, inclusive approach to win over voters.

The Pendulum Swing

Scaramucci uses the metaphor of a 'pendulum swinging back' to describe the current political climate, indicating a shift away from Trumpism and towards a more favorable environment for opposing political movements. This model suggests that political trends are cyclical and can be leveraged.

Lessons

  • Prioritize electoral victories over ideological purity: Focus on strategic voting and building broader coalitions to achieve political goals, even if it means aligning with those who don't share every value.
  • Engage in dialogue and maintain relationships: Rather than cutting off those with differing views, engage in conversations to foster understanding and potentially change hearts and minds over time, as demonstrated by personal anecdotes.
  • Choose battles wisely and avoid 'outrage porn': Concentrate efforts on significant issues that can lead to tangible change, and disengage from constant, unproductive outrage to maintain focus and energy for impactful action.

Leveraging Trump's Actions for Systemic Reform

1

Identify and document all instances where Donald Trump's administration flouted rules, norms, and standards of society.

2

Use this documented 'playbook' to pinpoint specific weaknesses in the democratic system that need strengthening.

3

Propose and implement reforms to these exposed weaknesses, ensuring that future leaders cannot exploit them in the same manner.

4

Build a broad political coalition focused on these reforms, appealing to those who prioritize the integrity of democratic processes over partisan divides.

Notable Moments

Anthony Scaramucci shares personal artifacts from his time in the White House, including a Stephen Colbert cartoon and a New Yorker cover that was never printed, to illustrate his journey and the importance of letting go.

This provides a personal, reflective dimension to the political discussion, showing how individuals can recover and learn from public setbacks, and reinforces the idea of not holding onto every grievance in the 'culture war'.

Daniel Grimes shares a deeply personal story about his father's evolution from homophobic views to acceptance after Daniel came out, emphasizing that keeping the door open for dialogue can lead to profound personal change.

This powerful anecdote serves as compelling evidence for the argument that engagement, rather than 'purity tests' or cutting people off, can transform deeply held prejudices and foster acceptance, even in politically charged environments.

Kelly Raymond recounts her mother-in-law's initial racist reaction to her biracial daughter, and how persistent engagement led to her becoming a 'phenomenal grandmother,' highlighting the importance of setting boundaries while still educating.

This story reinforces the theme that personal relationships and direct confrontation, when handled with clear boundaries, can overcome ingrained biases and lead to positive change within families and society.

Quotes

"

"The man who told you he wins so much that you would get tired of winning is having a very bad loser of a week."

Don Lemon
"

"It was a colossally bad week and I would say the beginning it's the beginning of the slow decline of Trumpism."

Anthony Scaramucci
"

"You're winning. The movement in the pendulum is swinging back. And I would just ask everybody, please understand there's a culture war going on and you don't have to win every point in the culture war. Go for the independents, okay? And you will get the country back away from these misgrants."

Anthony Scaramucci
"

"Trump has been so baldfaced about this, Don, that therein lies the opportunity to push the reform. He's almost exposed all the weaknesses in the system by flouting it."

Anthony Scaramucci
"

"You don't need to be prepared for the white side in life. But you do being a black person and having and having exposure to your culture and knowing who you are and and standing firm in that belief in who you are that you are just as good as and there's not a room that you don't belong in."

Kelly Raymond

Q&A

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