Podcast Summary: The Sage Steele Show

Episode: Who Will Cain Really Is (EP 80)
Air Date: November 5, 2025
Host: Sage Steele
Guest: Will Cain

Overview

This episode of The Sage Steele Show features an in-depth, candid, and often humorous conversation with Will Cain—host of Fox News' “The Will Cain Show” and “Will Cain Country.” Sage and Will, longtime friends and former ESPN colleagues, explore Will's non-traditional path from small-town Texas, to water polo at Pepperdine, to entrepreneurship, journalism, cable news, and ultimately national television and podcasting. The episode delves deeply into formative experiences, family loss, career pivots, handling controversy, the evolution of media, and the importance of authenticity and faith—all punctuated by lighthearted moments and genuine mutual respect.

Key Discussion Points & Insights

1. The Ritual of the Show—Setting the Tone

The episode begins playfully, with Sage’s tradition of making guests wear fuzzy socks. Will jokes about being a “barefoot” guy and remarks playfully on the effeminacy of socks, especially “floral” and “fuzzy” ones.
Memorable Moment: Will reluctantly but sportingly takes part, highlighting their camaraderie.
- “Now we've gone to another level.” (A, 03:18)

2. Upbringing and Formative Years in Texas and Montana

Will describes his childhood in Sherman, Texas, and his deep admiration for Western mythology and Steinbeck’s Travels with Charley.
After law school, Will spent a year in Montana working on a ranch and writing an “unpublishable” novel.
Life-Changing Event: During this period, Will’s father died by suicide—a deeply impactful event for Will and his family.
- “That was the year I honestly turned from a boy to a man.” (B, 10:19)

Notable Quotes:

“My dad killed himself when I was 25. My youngest brother was 15... I just never want to make that and my dad transactional...” (B, 13:40)
Will learned “to start and finish a project,” citing the discipline of writing and working a ranch.
He emphasizes the importance of action over rumination in healing and handling crisis.
“Action and time is the path for moving forward.” (B, 17:02)

3. Path to Media: Law, Journalism, and Entrepreneurial Detours

Will and Sage compare their early career dreams and pivots. Will initially planned to be a small-town lawyer, inspired by his father, but was ultimately drawn to ideas and debate.
Will’s unusual entry into media included buying and running small-town newspapers and launching a quinceañera magazine and events business (which eventually failed during the 2008-09 recession).
- “For me, waking up every day thinking about 15-year-old Hispanic girls was not my passion... If it were, call the FBI.” (B, 32:10)
Will's mantra: “I don’t take no from people that are not empowered to say yes.” (B, 39:44)

4. Break into National TV: Fox, CNN, ESPN

Will describes creating his own TV pilot, leveraging connections, and “cold-emailing” the President of CNN for an opportunity.
- “It was a shot in the dark and it worked.” (B, 38:50)
Sage and Will reflect on the pressure, adrenaline, and authenticity needed for TV, and Will's preparedness for televised debate.

5. ESPN Years: Debate, Humility & Challenges

Will discusses transitioning to ESPN, appearing on “First Take”, and squaring off with Stephen A. Smith.
- “You were never pounding the table to try to get him to believe what you… It was just a straight-up challenge, and no one had ever done that.” (A, 44:09)
Will emphasizes the show’s authenticity—debates weren’t contrived. He recalls heated moments, particularly on issues intersecting sports and race, but maintains he and colleagues like Stephen A. forged genuine friendships through these debates.
Insight: Will notes that being cast as the “contrarian” sometimes branded him, overshadowing his more nuanced personality, as discussed with Ryan Russillo.

6. On Controversy, Race, and Staying True to Values

Will details internet/social media backlash, being labeled a “racist” at both CNN and ESPN for legalistic, nuanced views—especially surrounding cases like Trayvon Martin and Colin Kaepernick.
Despite online hate, Will never considered softening or retreating:
- “That’s been my only North Star… Be you. Be real.” (B, 58:07)
Reflects on the different handling of internal bias and discipline at ESPN, particularly the shift after Trump’s election in 2016.
Memorable Exchange on ESPN’s shift:
- “When do you think ESPN turned?” (A, 61:54)
- “Well, when Trump was elected president the first time, it turned everything over. Not just ESPN, everything…” (B, 62:07)

7. Reflections on the Media Landscape & ESPN’s Decline

Both express sadness for the loss of ESPN’s broad cultural appeal.
Will notes ESPN, though still watched, “is not as relevant as it used to be.” (B, 74:36)
Key insight: fragmentation of consumption—“the multitude of choices” diluting singular cultural platforms like ESPN.
Sage and Will both lament the loss of ideological diversity and tolerance at the network.

8. Authenticity, Loyalty, and Chemistry On-Air

Will credits his late-in-life media break for helping him stay grounded and unaffected by “fame.”
Discusses the genuine “lightning in a bottle” chemistry with Fox co-hosts Pete Hegseth and Rachel Campos-Duffy on “Fox & Friends Weekend.”
- “Nothing like what I have with Pete… and Rachel.” (B, 84:01)

9. Community, Giving Back, and the Hawaii Wildfire Relief

Will’s personal connection to Hawaii—his mother was there during the Lahaina wildfires.
He spearheaded a GoFundMe campaign raising $2.6 million, personally vetting recipients and distributing grants, saying it “changed me for the rest of my life.”
- “That was the fulfillment of making this job really meaningful.” (B, 90:11)

10. Faith, Family, and Legacy

Will is humbled by his ability to do his show from Texas, thanks to Fox, restoring family/work-life balance and a deep connection to his roots.
- “I am always and forever from Sherman, Texas.” (B, 102:00)
On what he wants to be remembered for:
- “I just want to be real… I want to be real with every person I interact with.” (B, 103:31)
Sage compliments Will on his integrity and nontraditional, uncompromising career.

11. Lighter Moments & Personal Oddities

Will shares a colorful, step-by-step account of his life-long relationship with chewing tobacco, now replaced by nicotine “Zen” pouches—anecdotes offered self-deprecatingly, adding warmth and relatability to the episode. (80:00–82:34)
Sage teases Will about Texas stereotypes, and Will delivers with gusto.

Notable Quotes & Timestamps

On handling personal tragedy:
- “I just never want to make that and my dad transactional in this… even talking to you now, I don’t want you to feel sorry for me.” — Will (13:40)
On debate and performance:
- “You just can’t do this to try to be famous… The reason I did this is because I thought there was something missing in the conversation that I could provide.” — Will (24:06)
On authenticity:
- “That’s been my only North Star, my only guiding light. Be you. Be real.” — Will (58:07)
On ESPN’s cultural decline:
- “I don’t think it matters… It’s not as relevant as it used to be.” — Will (74:31)
On the meaning of his career:
- “I can’t just make money from it. I have to do more with the privilege and platform that I’ve been given.” — Will (90:11)
On legacy:
- “I just want to be real… I want to be real with every person I interact with.” — Will (103:31)

Section Timestamps

[00:00–03:30] — Playful intro, socks tradition
[05:00–13:30] — Montana, family loss, transition to adulthood
[18:40–24:00] — Water polo, Pepperdine, and handling humility through sports
[24:45–33:47] — Law, small-town newspapers, business ventures, and pivotal failures
[35:30–41:18] — Breaking into TV, CNN and Fox, authenticity on air
[44:09–49:06] — ESPN First Take, debate culture, handling identity and controversy
[54:02–64:06] — Facing race, controversy, ESPN’s political turn
[75:24–84:26] — Fox & Friends chemistry, and the challenges of creating authentic TV ensembles
[86:29–90:56] — Lahaina wildfires, humanitarian work, and the deeper fulfillment of public platform
[95:37–98:45] — On media bias, Fox vs. CNN, objectivity and honesty
[100:43–102:00] — Coming home to Texas, meaning of roots and hometown honor
[103:26–105:36] — Closing reflections on legacy, authenticity, and gratitude

Final Thoughts

This episode is a masterclass in open, reflective podcast conversation. Will Kane’s journey is equal parts rugged individualism, intellectual ambition, and heartfelt service. Sage’s deeply informed and empathetic questioning draws out Will’s lesser-known stories, guiding the discussion with humor and heart. Listeners are left with a rich portrait of perseverance, a commitment to truth and loyalty, and the value of staying real—even (perhaps especially) in the pressure-cooker world of modern media.

Podcast Summary: The Sage Steele Show

Episode: Who Will Cain Really Is (EP 80)
Air Date: November 5, 2025
Host: Sage Steele
Guest: Will Cain

Overview

Key Discussion Points & Insights

1. The Ritual of the Show—Setting the Tone

The episode begins playfully, with Sage’s tradition of making guests wear fuzzy socks. Will jokes about being a “barefoot” guy and remarks playfully on the effeminacy of socks, especially “floral” and “fuzzy” ones.
Memorable Moment: Will reluctantly but sportingly takes part, highlighting their camaraderie.
- “Now we've gone to another level.” (A, 03:18)

2. Upbringing and Formative Years in Texas and Montana

Will describes his childhood in Sherman, Texas, and his deep admiration for Western mythology and Steinbeck’s Travels with Charley.
After law school, Will spent a year in Montana working on a ranch and writing an “unpublishable” novel.
Life-Changing Event: During this period, Will’s father died by suicide—a deeply impactful event for Will and his family.
- “That was the year I honestly turned from a boy to a man.” (B, 10:19)

Notable Quotes:

“My dad killed himself when I was 25. My youngest brother was 15... I just never want to make that and my dad transactional...” (B, 13:40)
Will learned “to start and finish a project,” citing the discipline of writing and working a ranch.
He emphasizes the importance of action over rumination in healing and handling crisis.
“Action and time is the path for moving forward.” (B, 17:02)

3. Path to Media: Law, Journalism, and Entrepreneurial Detours

Will and Sage compare their early career dreams and pivots. Will initially planned to be a small-town lawyer, inspired by his father, but was ultimately drawn to ideas and debate.
Will’s unusual entry into media included buying and running small-town newspapers and launching a quinceañera magazine and events business (which eventually failed during the 2008-09 recession).
- “For me, waking up every day thinking about 15-year-old Hispanic girls was not my passion... If it were, call the FBI.” (B, 32:10)
Will's mantra: “I don’t take no from people that are not empowered to say yes.” (B, 39:44)

4. Break into National TV: Fox, CNN, ESPN

Will describes creating his own TV pilot, leveraging connections, and “cold-emailing” the President of CNN for an opportunity.
- “It was a shot in the dark and it worked.” (B, 38:50)
Sage and Will reflect on the pressure, adrenaline, and authenticity needed for TV, and Will's preparedness for televised debate.

5. ESPN Years: Debate, Humility & Challenges

Will discusses transitioning to ESPN, appearing on “First Take”, and squaring off with Stephen A. Smith.
- “You were never pounding the table to try to get him to believe what you… It was just a straight-up challenge, and no one had ever done that.” (A, 44:09)
Will emphasizes the show’s authenticity—debates weren’t contrived. He recalls heated moments, particularly on issues intersecting sports and race, but maintains he and colleagues like Stephen A. forged genuine friendships through these debates.
Insight: Will notes that being cast as the “contrarian” sometimes branded him, overshadowing his more nuanced personality, as discussed with Ryan Russillo.

6. On Controversy, Race, and Staying True to Values

Will details internet/social media backlash, being labeled a “racist” at both CNN and ESPN for legalistic, nuanced views—especially surrounding cases like Trayvon Martin and Colin Kaepernick.
Despite online hate, Will never considered softening or retreating:
- “That’s been my only North Star… Be you. Be real.” (B, 58:07)
Reflects on the different handling of internal bias and discipline at ESPN, particularly the shift after Trump’s election in 2016.
Memorable Exchange on ESPN’s shift:
- “When do you think ESPN turned?” (A, 61:54)
- “Well, when Trump was elected president the first time, it turned everything over. Not just ESPN, everything…” (B, 62:07)

7. Reflections on the Media Landscape & ESPN’s Decline

Both express sadness for the loss of ESPN’s broad cultural appeal.
Will notes ESPN, though still watched, “is not as relevant as it used to be.” (B, 74:36)
Key insight: fragmentation of consumption—“the multitude of choices” diluting singular cultural platforms like ESPN.
Sage and Will both lament the loss of ideological diversity and tolerance at the network.

8. Authenticity, Loyalty, and Chemistry On-Air

Will credits his late-in-life media break for helping him stay grounded and unaffected by “fame.”
Discusses the genuine “lightning in a bottle” chemistry with Fox co-hosts Pete Hegseth and Rachel Campos-Duffy on “Fox & Friends Weekend.”
- “Nothing like what I have with Pete… and Rachel.” (B, 84:01)

9. Community, Giving Back, and the Hawaii Wildfire Relief

Will’s personal connection to Hawaii—his mother was there during the Lahaina wildfires.
He spearheaded a GoFundMe campaign raising $2.6 million, personally vetting recipients and distributing grants, saying it “changed me for the rest of my life.”
- “That was the fulfillment of making this job really meaningful.” (B, 90:11)

10. Faith, Family, and Legacy

Will is humbled by his ability to do his show from Texas, thanks to Fox, restoring family/work-life balance and a deep connection to his roots.
- “I am always and forever from Sherman, Texas.” (B, 102:00)
On what he wants to be remembered for:
- “I just want to be real… I want to be real with every person I interact with.” (B, 103:31)
Sage compliments Will on his integrity and nontraditional, uncompromising career.

11. Lighter Moments & Personal Oddities

Will shares a colorful, step-by-step account of his life-long relationship with chewing tobacco, now replaced by nicotine “Zen” pouches—anecdotes offered self-deprecatingly, adding warmth and relatability to the episode. (80:00–82:34)
Sage teases Will about Texas stereotypes, and Will delivers with gusto.

Notable Quotes & Timestamps

On handling personal tragedy:
- “I just never want to make that and my dad transactional in this… even talking to you now, I don’t want you to feel sorry for me.” — Will (13:40)
On debate and performance:
- “You just can’t do this to try to be famous… The reason I did this is because I thought there was something missing in the conversation that I could provide.” — Will (24:06)
On authenticity:
- “That’s been my only North Star, my only guiding light. Be you. Be real.” — Will (58:07)
On ESPN’s cultural decline:
- “I don’t think it matters… It’s not as relevant as it used to be.” — Will (74:31)
On the meaning of his career:
- “I can’t just make money from it. I have to do more with the privilege and platform that I’ve been given.” — Will (90:11)
On legacy:
- “I just want to be real… I want to be real with every person I interact with.” — Will (103:31)

Section Timestamps

[00:00–03:30] — Playful intro, socks tradition
[05:00–13:30] — Montana, family loss, transition to adulthood
[18:40–24:00] — Water polo, Pepperdine, and handling humility through sports
[24:45–33:47] — Law, small-town newspapers, business ventures, and pivotal failures
[35:30–41:18] — Breaking into TV, CNN and Fox, authenticity on air
[44:09–49:06] — ESPN First Take, debate culture, handling identity and controversy
[54:02–64:06] — Facing race, controversy, ESPN’s political turn
[75:24–84:26] — Fox & Friends chemistry, and the challenges of creating authentic TV ensembles
[86:29–90:56] — Lahaina wildfires, humanitarian work, and the deeper fulfillment of public platform
[95:37–98:45] — On media bias, Fox vs. CNN, objectivity and honesty
[100:43–102:00] — Coming home to Texas, meaning of roots and hometown honor
[103:26–105:36] — Closing reflections on legacy, authenticity, and gratitude

Who Will Cain Really Is | Sage Steele Show | EP 80

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Summary

Podcast Summary: The Sage Steele Show

Overview

Key Discussion Points & Insights

1. The Ritual of the Show—Setting the Tone

2. Upbringing and Formative Years in Texas and Montana

Notable Quotes:

3. Path to Media: Law, Journalism, and Entrepreneurial Detours

4. Break into National TV: Fox, CNN, ESPN

5. ESPN Years: Debate, Humility & Challenges

6. On Controversy, Race, and Staying True to Values

7. Reflections on the Media Landscape & ESPN’s Decline

8. Authenticity, Loyalty, and Chemistry On-Air

9. Community, Giving Back, and the Hawaii Wildfire Relief

10. Faith, Family, and Legacy

11. Lighter Moments & Personal Oddities

Notable Quotes & Timestamps

Section Timestamps

Final Thoughts

Summary

Podcast Summary: The Sage Steele Show

Overview

Key Discussion Points & Insights

1. The Ritual of the Show—Setting the Tone

2. Upbringing and Formative Years in Texas and Montana

Notable Quotes:

3. Path to Media: Law, Journalism, and Entrepreneurial Detours

4. Break into National TV: Fox, CNN, ESPN

5. ESPN Years: Debate, Humility & Challenges

6. On Controversy, Race, and Staying True to Values

7. Reflections on the Media Landscape & ESPN’s Decline

8. Authenticity, Loyalty, and Chemistry On-Air

9. Community, Giving Back, and the Hawaii Wildfire Relief

10. Faith, Family, and Legacy

11. Lighter Moments & Personal Oddities

Notable Quotes & Timestamps

Section Timestamps

Final Thoughts