Ruthless Podcast — "Remembering Charlie Kirk" (September 11, 2025)

Hosts: Josh Holmes, Comfortably Smug, Michael Duncan, John Ashbrook
Special Guest: Senator Sheehy (Montana)

Episode Overview

This episode deviates from the usual lighter tone of Ruthless, focusing instead on processing the shocking assassination of conservative activist Charlie Kirk. The hosts forgo their trademark humor, offering heartfelt reflections on Kirk’s legacy, the current state of political violence, and the challenges facing American society. The episode also features a timely interview with Sen. Sheehy, recorded shortly after news of the shooting broke, adding broader context on political discourse, violence, and resilience.

Main Themes

• Remembrance and Legacy of Charlie Kirk:
  Reflections on Kirk's influence in conservative politics, especially among young people and in new media.
• Condemnation of Political Violence:
  Discussion of recent trends in political violence and the dangerous polarization in America.
• Character and Exemplary Leadership:
  Highlighting Kirk’s personal traits—his courage, faith, affability, and approach to debate.
• Frustration and Anger at Media and Cultural Responses:
  Critique of reactions from left-leaning media figures and online communities celebrating or excusing the violence.
• Coping with Grief and the Way Forward:
  Emphasis on resilience, the importance of continued civil discourse, and the need to honor Kirk’s legacy by persisting against fear.

Key Discussion Points & Insights

1. Charlie Kirk’s Impact and Unique Presence [(00:00–08:36)]

• Personal Reflections:
  The hosts are visibly shaken, emphasizing the personal and communal loss.

  • "There are no words to describe the collective emotion that we... have dealt with over the last 18 hours or so since you’ve heard about the passing of Charlie Kirk." — Josh Holmes [00:00]

• Legacy in Conservative Youth Movement:

  • Will Kane (Fox News) eulogizes Kirk:
    "No one has marshaled the youth in this country in my lifetime in the way of Charlie Kirk... His influence didn’t stop on college campuses. Charlie Kirk’s influence extended onto the heights of power in the United States of America." — Will Kane, featured clip [02:19]
  • Reflection on how Kirk normalized conservative engagement on college campuses.
  • Kirk as a personal connector, supporting colleagues in a business filled with competition.

• Kirk’s Courage and Conduct:

  • "He did one of the hardest things in politics as a conservative, and that is show up on college campuses... it was never a meanness to any of it." — Michael Duncan [05:23]

• Family and the Human Cost:

  • The hosts grieve for Kirk’s young children.
    "His kids are so little. They can’t read. They don’t understand what’s happened to them. But when they get older, think about how proud they're going to be of their dad." — John Ashbrook [07:35]

2. Processing Grief, Anger, and Political Division [(08:36–24:02)]

• The Rage and Sorrow:
  The hosts discuss their brewing anger at both the event itself and the reactions online and in media.

  • "I'm just filled with so much anger as I looked at those pictures of a 1 year old and a 3 year old who will not have their father because the left has lost its goddamn mind." — Michael Duncan [09:11]
  • Recognition that conservative disagreements pale in comparison to existential threats from escalating political violence.

• Rejection of Exploitative Reactions:
  Critique of those who seek social media clout from Kirk’s death or use the incident for political point scoring.

• Political Violence—Historical Context:

  • Parallels to the late 1960s; recounting incidents of attacks on politicians and public figures.
    "I just have to believe at some level that we’re not going to tip into 1968. Like, I just... have to believe that we’re not going to go down that road." — Josh Holmes [13:02]

• The Social Media Information Silo:

  • The internet facilitates dehumanization, hate, and celebration of violence.
  • "It is absolutely a sickness. It's a disease. And these people on TikTok are demons." — John Ashbrook [20:50]

• Character Amidst Hostility:
  The hosts note Kirk’s composure even amongst hostile protesters:

  • "His reaction was peaceful. And, like, I think that is a testament to his character." — Michael Duncan [23:31]

3. Lessons for the Moment and Future [(24:02–30:00)]

• Resilience in the Face of Violence:

  • The importance of continuing the work, unafraid.
    "You have to live unafraid of these people. That’s how we win." — Michael Duncan [28:07]
  • Comparing Kirk’s “happy warrior” mentality to other conservative figures willing to confront hostile environments.

• The Importance of the Battle of Ideas:

  • "Violence is not going to solve anything. Retribution never in that capacity ever does in this country. It may in others… but in the United States, a battle of ideas is just won by people who actually just commit to it. And that’s what Charlie was committed to." — Josh Holmes [25:50]

• Addressing the Audience:

  • The hosts urge listeners not to be paralyzed by despair, but to honor Kirk’s legacy by persisting in civil, courageous engagement.

Notable Quotes & Memorable Moments

• "Every single one of us would get a text, would get a direct message, would get a call from Charlie, encouraging us, congratulating us, complimenting a conversation or a segment. In a business that is full of ego... Charlie Kirk was a true friend." — Will Kane [02:19]
• "You look at some of the great leaders of our time and you think about what their reaction to tragedy is. I'm urging you all... do not get despondent. Violence is not going to solve anything… a battle of ideas is just won by people who actually just commit to it. And that's what Charlie was committed to." — Josh Holmes [25:50]
• "You've got to keep doing. You've got to keep going. That's what Charlie did. And all of us were in admiration for the idea that he did what he would do." — Josh Holmes [28:13]
• "We are honored to have that guy in the Senate." — Michael Duncan, on Senator Sheehy [53:55]

Senator Sheehy Interview Highlights [(30:05–53:11)]

Reaction to Charlie Kirk’s Assassination

• Sen. Sheehy calls for rejecting political violence, emphasizing the mounting normalization of such acts.
  • "There’s just no excuse for political violence… we’ve got to figure out how to talk to each other again." — Senator Sheehy [30:05]

Political and Societal Context

• Draws parallels to violence abroad and in America.
• Remembers the Trump assassination attempt and the resilience required to persist in public life after such events.

Public Service and Problem-Solving

• Shares his approach to solving bipartisan issues like wildfires, drawing on previous experience as a firefighter and outsider.
  • "We have to stop watching our cities burn to the ground. And I just loved that. That was very cool." — Michael Duncan quoting Sheehy [35:10]
• Emphasizes the necessity of coalitions and pragmatic, non-ideological problem solving in the Senate.
  • "The whole concept of legislating is building a coalition around an issue... to get anything done, there has to be some understanding that you have to have a persuasive quality and you have to get to know people." — Josh Holmes [44:01]
• Candidly describes navigating Senate relationships as akin to partnerships in military missions.

9/11 Anniversary Reflections

• Sheehy relates his own life trajectory and call to service to the attacks of September 11th.
  • "Everyone knows where they were... life divided into a before and after..." — Senator Sheehy [47:01]

Crime and Political Dysfunction

• Blames rising crime and disorder on ideological capture within the Democratic Party.
  • "Americans want secure border, safe streets, cheap gas, cops are good, criminals are bad, boys are boys, girls are girls." — Senator Sheehy [52:34]

Closing Moments

• The hosts reaffirm their gratitude for conservative leaders like Kirk and Sheehy, express ongoing grief, and urge listeners to keep Kirk’s family in their prayers.
• "Thank you, everyone, for listening honestly. And please keep Charlie’s family in your prayers. I can't imagine what they're going through." — Comfortably Smug [54:50]

Timestamps for Key Segments

• [00:00] – Reflections on Kirk’s death; tone set for the episode
• [02:19] – Will Kane’s tribute
• [05:23] – Kirk’s conduct on campuses, legacy for youth
• [07:35] – Family, fatherhood, and loss
• [09:11] – Anger and political context
• [13:02] – Political violence, historical parallels
• [18:04] – Media/social media reactions, critique
• [23:31] – Kirk's composure in debate
• [24:02] – Guidance for coping and resilience
• [28:07] – Living unafraid; how to continue
• [30:05] – Introduction to Senator Sheehy interview; his reaction to the shooting
• [35:10] – Problem-solving approach in public policy
• [41:24] – Senate observations, collaboration
• [47:01] – 9/11 memories and national context
• [52:34] – Soundbite summary of common sense values
• [53:55] – Reflections and bringing the discussion full circle
• [54:50] – Final thoughts and sign-off

Tone & Language

The episode is deeply raw and emotional, with hosts oscillating between grief, anger, admiration, and a call to resilience. The language is candid, unscripted, at times explicit, and shaped by the hosts’ personal connections to the subject and audience.

Takeaways

• Charlie Kirk’s legacy is one of courage, optimism, and the willingness to engage with ideological opponents without malice.
• The episode serves as a caution against political and media dehumanization leading to violence.
• The Ruthless team calls for unity, consistent engagement in the public square, and honoring Kirk by defending civil discourse and conservative values without succumbing to fear or hatred.