The Woke Left Can’t Stand Her — Virginia’s Gubernatorial Candidate Winsome Earle-Sears Won’t Back Down episode artwork

EPISODE · Oct 22, 2025 · 1H 21M

The Woke Left Can’t Stand Her — Virginia’s Gubernatorial Candidate Winsome Earle-Sears Won’t Back Down

from Keeping It Real: Conversations with Jillian Michaels · host Jillian Michaels

The Trump-Endorsed Gubernatorial Candidate Lt. Gov. Winsome Earle-Sears came to America from Jamaica with nothing but grit and a dream — and made history. A U.S. Marine Corps veteran, small business owner, and Virginia’s first woman of color ever elected statewide, Winsome Earle-Sears shattered barriers to become Lieutenant Governor — and now, she’s running for governor. In this powerful episode, Winsome opens up about the beliefs and experiences that shaped her journey: her positions on abortion, gay marriage, ICE, Immigration, DEI, and right-to-work laws; the Jay Jones controversy that ignited debate across Virginia; and her bold vision for a state united by freedom, opportunity, and accountability — not identity politics. For the first time, she also speaks from the heart about the tragic loss of her daughter, and how that pain transformed her into a more compassionate, purpose-driven leader. Courage, conviction, and compassion — Get to know the firebrand that is taking Virginia’s gubernatorial race by storm.  Learn more about your ad choices. Visit megaphone.fm/adchoices

The Trump-Endorsed Gubernatorial Candidate Lt. Gov. Winsome Earle-Sears came to America from Jamaica with nothing but grit and a dream — and made history. A U.S. Marine Corps veteran, small business owner, and Virginia’s first woman of color ever elected statewide, Winsome Earle-Sears shattered barriers to become Lieutenant Governor — and now, she’s running for governor. In this powerful episode, Winsome opens up about the beliefs and experiences that shaped her journey: her positions on abortion, gay marriage, ICE, Immigration, DEI, and right-to-work laws; the Jay Jones controversy that ignited debate across Virginia; and her bold vision for a state united by freedom, opportunity, and accountability — not identity politics. For the first time, she also speaks from the heart about the tragic loss of her daughter, and how that pain transformed her into a more compassionate, purpose-driven leader. Courage, conviction, and compassion — Get to know the firebrand that is taking Virginia’s gubernatorial race by storm.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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The Woke Left Can’t Stand Her — Virginia’s Gubernatorial Candidate Winsome Earle-Sears Won’t Back Down

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How long is this episode of Keeping It Real: Conversations with Jillian Michaels?

This episode is 1 hour and 21 minutes long.

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This episode was published on October 22, 2025.

What is this episode about?

The Trump-Endorsed Gubernatorial Candidate Lt. Gov. Winsome Earle-Sears came to America from Jamaica with nothing but grit and a dream — and made history. A U.S. Marine Corps veteran, small business owner, and Virginia’s first woman of color ever...

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