Podcast Summary

Podcast: Keeping It Real: Conversations with Jillian Michaels
Host: Jillian Michaels
Episode: The Woke Left Can’t Stand Her — Virginia’s Gubernatorial Candidate Winsome Earle-Sears Won’t Back Down
Release Date: October 22, 2025
Guest: Winsome Earle-Sears (Virginia Lieutenant Governor, Gubernatorial Candidate)

Episode Overview

In this powerful episode, Jillian Michaels sits down with Winsome Earle-Sears—Jamaican immigrant, U.S. Marine Corps veteran, small business owner, and current Lieutenant Governor of Virginia. With candor and depth, the conversation traverses topics from the American immigrant experience to the vitriolic attacks Earle-Sears faces and her policy stances on immigration, LGBTQ+ rights, abortion, law enforcement, unions, and economic development. Both women tackle political double standards, media bias, and the ways in which culture wars distract from pressing societal issues. The episode is also profoundly personal, as Earle-Sears shares the impact of losing her daughter and grandchildren, and how tragedy shapes her resilience and leadership.

Key Discussion Points & Insights

1. Winsome Earle-Sears: The American Story

[03:30–06:24]

• Jillian introduces Earle-Sears as a Jamaican immigrant whose father arrived with just $75 and a vision for opportunity in the U.S.
• Winsome relays that her father had to prove he wouldn’t be a burden on taxpayers before immigrating.
• Emphasizes legal immigration as beneficial: “He thought that America is where he would restart his life... he chose America because he figured this is...where the jobs and the opportunities were.” (Winsome, [05:08])

2. Immigration: Laws, Borders, and Crime

[07:29–09:14]

• Immigration must be legal and managed, with the “front door” metaphor for borders.
• Earle-Sears criticizes her opponent Abigail Spanberger for supporting open borders: “As a result...fentanyl came through, killing five Virginians every week. We had sex trafficking happen. We had every kind of trafficking happen.” (Winsome, [08:07])

3. Personal Identity, Double Standards, and Vicious Attacks

[11:25–17:40]

• Jillian remarks on Earle-Sears’s paradoxical position as the ideal for liberal identity politics, yet subject to vicious attacks for not conforming politically.
• Reads aloud hate mail Earle-Sears has received (with slurs redacted).
• Winsome’s response: “These are from the people who are tolerant. If this is what their love looks like, God help us. ... do good anyway, because it was never between you and them. It was between you and God.” (Winsome, [13:03])

4. Media Bias and Political Hypocrisy

[15:06–17:51]

• Discussing how media frames Republican women of color more harshly and ignores abuse when aimed at conservatives.
• “If the Republicans had done that to a black female who is Democrat, just call the race over. ...But apparently it's okay when the Democrats do it to a black female Republican. You see the double standard.” (Winsome, [16:23])

5. Policy on LGBTQ+ Rights

[20:34–22:10]

• Clarifies she would not pursue any policy to overturn marriage equality: “No, absolutely not...I want everybody to make the best of themselves, whatever that is. And as governor, I represent everybody.” (Winsome, [20:48 & 22:10])
• Critiques how the left weaponizes the issue and spreads misinformation about conservatives on LGBTQ+ rights.

6. Abortion: State Rights and Nuance

[28:40–33:57]

• Earle-Sears emphasizes her stance: letting Virginians decide via constitutional amendment.
• Criticizes her opponent’s position as extreme (up to birth), and says her own position allows for exceptions for rape, incest, and health of the mother.
• “My position is this: we've got to come together as the Commonwealth and figure out where we want to be on it. ...It's not going to be my policy, it's going to be the policy of the majority.” (Winsome, [28:40])

7. Unions, Right to Work, and Economic Policy

[40:33–44:19]

• Right to work defined as workers not being forced to join unions or pay dues.
• Explains, “That's not freedom, that's not liberty...I must be able to work without being forced to join a union.” (Winsome, [41:43])
• Connects big union money to political loyalty and lack of worker agency.
• Highlights how culture wars distract from these critical economic issues.

8. Law Enforcement, Safety, and Qualified Immunity

[46:17–50:31]

• Earle-Sears blames rising crime on anti-police policies and emphasizes the importance of qualified immunity for officers’ personal protection.
• “If you don't win, we're not staying because we'll lose everything.” (Winsome, quoting law enforcement, [47:54])
• 81 out of Virginia’s sheriffs support Winsome.

9. Homelessness, State Spending, and the Problem with Big Government

[50:31–52:29]

• Criticizes endless government programs and lack of accountability.
• “We have these liberals who want to be kind with my tax money.” (Winsome, [51:22])
• Proposes a tax form option for voluntarism: “Tell us how much more you want us to tax you, and we will send you a Golden thank you letter.” (Winsome, [52:29])

10. Reflections on Socialism, History, and Policy Lessons

[55:28–59:06]

• Draws on her experience growing up in Jamaica under socialism: state took over property, rich-poor chasm grew, economy collapsed.
• “Jamaica was now a socialist democrat country...businesses immediately fled...the state would now own everything.” (Winsome, [55:49])
• Argues Americans must learn from international history and avoid similar policy mistakes.

11. Personal Tragedy and Mental Health Advocacy

[70:26–77:32]

• In a deeply moving segment, Winsome recounts the loss of her daughter and two grandchildren:
• “Here I am in the church, and I'm looking at three caskets. ... that's why I'm saying, you want to live that way, live that way. ...But let's find a way to love each other... I don't know, let's agree to disagree.” (Winsome, [71:03])
• Talks about lessons in compassion and empathy she brings to her public service.

12. Closing: On Dialogue, Respect, and Pragmatism

[78:56–82:55]

• Calls for respectful, fact-based debate and working together for the good of all.
• “I can lose it by myself, but I can't win it by myself. We all play this role in making sure that we have the ability to have a Virginia that works for everybody. And my policies will.” (Winsome, [82:12])

Notable Quotes & Memorable Moments

• On Racist Attacks:
  “These are from the people who are tolerant. If this is what their love looks like, God help us.” (Winsome Earle-Sears, [13:03])

• On Double Standards:
  “If the Republicans had done that... the Republican Party would be done forevermore, never to be spoken of again. But apparently it's okay when the Democrats do it to a black female Republican.” (Winsome, [16:23])

• On LGBTQ+ Rights:
  “I am not about to take away anyone's rights. ...I want everybody to make the best self, the best of themselves, whatever that is. And as governor, I represent everybody.” (Winsome, [22:10])

• On Losing Her Daughter and Grandchildren:
  “Here I am in the church, and I'm looking at three caskets. Not one, not two, but three. ...Life is too short.” (Winsome, [71:03])

• On Abortion:
  “My position is this: we've got to come together as the Commonwealth and figure out where we want to be on it. ...It's not going to be my policy, it's going to be the policy of the majority.” (Winsome, [28:40])

• On Economic Policy:
  “That's not freedom, that's not liberty...I must be able to work without being forced to join a union.” (Winsome, [41:43])

• On Immigration and Law Enforcement:
  “We have to be a nation of laws, and if you commit the crime, you are going to do the time. It's that simple. ...You gotta go home.” (Winsome, [63:13])

• On Working Together:
  “I can lose it by myself, but I can't win it by myself. We all play this role in making sure that we have the ability to have a Virginia that works for everybody.” (Winsome, [82:12])

Important Timestamps

• 03:30 – Winsome’s immigrant story and family background
• 07:29 – Immigration policy and border security
• 11:25 – Breaking identity expectations, hate mail examples
• 16:23 – Media’s double standard
• 20:34 – LGBTQ+ rights stance
• 28:40 – Abortion stance and constitutional amendment
• 40:33 – Right to work, unions, and economic liberty
• 46:17 – Law enforcement, qualified immunity, and safety
• 50:31 – Homelessness, funding, and government programs
• 55:28 – Lessons from socialism in Jamaica
• 70:26 – Personal loss: mental health, daughter and grandchildren
• 78:56 – Commitment to open debate, dialogue, and respectful disagreement

Episode Tone & Language

The discussion is frank, emotional, and pragmatic, with both host and guest committed to “keeping it real”—calling out hypocrisy, misinformation, and the importance of fact-based dialogue. Despite differences in background and some beliefs, the tone is one of mutual respect and shared concern for policy over partisanship. Winsome Earle-Sears comes across as honest, resilient, and guided by her personal faith and life experience.

Conclusion

This episode offers a deep dive into both the personal convictions and policy priorities of Winsome Earle-Sears, painting a nuanced portrait of what it means to lead fearlessly in today’s political climate. For listeners seeking a mix of political analysis, personal storytelling, and thoughtful debate on contentious issues, this is a must-hear conversation—one that insists the ultimate solutions must be pragmatic, fair, and rooted in shared American values.