The Dan Le Batard Show with Stugotz

Hour 2: Stephen A. Smith (feat. Stephen A. Smith)
Date: August 21, 2025

Overview

Live from the Elser Hotel in Downtown Miami, Dan Le Batard, Stugotz, and the crew host an intimate, wide-ranging conversation with Stephen A. Smith. The episode dives deep into Stephen A.'s sprawling media career, his improbable comeback from adversity, his philosophy on “working within the corporate machine,” relationships publicly and privately (including candid remarks about LeBron James and Jerry Jones), and a personal look at family, legacy, and the power—and limits—of ambition. The tone oscillates between playful banter and earnest reflection, offering listeners Stephen A.'s indomitable personality paired with moments of vulnerability.

Key Discussion Points & Insights

1. Stephen A. Smith’s Relentless Work Ethic and Media Expansion

• Stephen A. on Loving His Work

  • Despite relentless travel and a hectic schedule, Stephen A. emphasizes his passion for the job.
    • "That's because I love what I do. I'm having a good time. I'm just traveling right now." [01:53]
  • He apologizes for being late due to airport security (even with CLEAR), joking about his celebrity not getting him through faster—"I'm not too big for that. Private jets are expensive!" [02:41]

• Career & Media Ownership

  • Stephen A. discusses his two new SiriusXM shows (sports and politics), the importance of not being one-dimensional, and strategic partnership deals.
    • "I've always been a conscientious observer and I've always been somebody that's looking not to be one-dimensional." [03:28]
    • "Ownership of my own YouTube channels and my production company...creating scripted and unscripted content..." [03:57]

2. Resilience and Improbable Comeback

• Getting Fired from ESPN and Persevering Through Blackballing

  • Stephen A. recalls being fired in 2009 and describes the following years as a near-total ban from TV and the industry.
    • “I was essentially banned, in my estimation, blackballed… considered somebody that you didn’t want to do business with.” [04:56]

• The Fear That Drives Him

  • He reveals the deep fear and insecurity that continue to motivate him, rooted in his upbringing and family obligations:
    • "I was a new dad...knowing what welfare cheese and bread is like...I was absolutely, positively petrified...if I didn't get something together." [06:32]
    • "At the snap of a finger, it can all be taken away from me. That is how I approach my everyday life… It’s who I am." [07:23]

3. Navigating Corporate Media and Remaining Authentic

• Balancing Authenticity and Responsibility

  • Stephen A. explains the need to maintain authenticity while understanding organizational expectations:
    • “I've always prided myself on being as true to me as I can possibly be, but being mindful of the fact that I don’t just represent myself.” [10:21]
  • Contrasts his approach with Dan’s more rebellious tendencies:
    • “Sometimes you’re so, so passionate that you’ll win the battle and lose the war…You’re too damn important.” [11:28]

• Learning from Hardship in Media

  • References past highly contentious moments in his career and arbitration battles, marking a difference in temperament and strategy compared to Dan:
    • “There was times...trouble has always followed me...I’m gonna say the things that need to be said…sometimes it's gonna ruffle feathers.” [12:21]
    • “Some fights…ain’t worth a damn...and then there are some bigger fights where somebody needs to get their ass kicked.” [13:41]

4. Media Business, Journalism, and the NFL’s Stake in ESPN

• On the NFL’s 10% Ownership of ESPN

  • Stephen A. addresses concerns over the NFL's influence on journalism at ESPN after purchasing a stake in the company, maintaining confidence in journalistic integrity:
    • "We live in a different age and everybody's in business with somebody...I don't think so [that it compromises journalism]." [14:36]
    • “...No deal between the league and ESPN is going to stop me from being me.” [17:11]

• Dan Presses on the Changing Media Landscape

  • Dan and Stephen A. debate if true independence is even possible moving forward, with Stephen A. insistent that while pressures exist, standards won’t automatically drop:
    • “...The integrity that comes with ESPN and how we do what we do is not going to be compromised just because you got a piece of ownership.” [21:16]

5. Relationships: LeBron James, Skip Bayless, Shannon Sharpe, and Family

• LeBron James: A Candid Rift

  • Stephen A. confirms there is “zero” relationship with LeBron, tracing the animosity to a game confrontation and accusations of attacking LeBron’s family:
    • “I don’t like him. He doesn’t like me. We don’t like each other. It is what it is…That’s a line you don’t get to come back from.” [23:10]
    • “I’ve never said a negative word [about Bronny James] until...he got scorched.” [24:54]

• Skip Bayless and Shannon Sharpe

  • Stephen A. expresses gratitude for both, despite limited off-air relationship with Skip:
    • “He pushed for me to be on First Take, which obviously played a pivotal role in resurrecting my career.” [28:30]
    • “With Shannon...our friendship developed, our brotherhood developed. I got a lot of love for him.” [28:30]

• Family: Daughters and His Late Mother

  • Joyful stories about his daughters' playful ribbing and their different personalities (Samantha, an aspiring actress/lawyer; Nyla, “the socialist” who prefers to be behind the scenes).

    • "My daughters...when they do good in school...there’s nothing they can’t get from me.” [32:33]
    • “They tease me about my forehead, my receding hairline—'dad, at some point you gotta let it go.'” [34:43]

  • On his mother’s passing and its emotional legacy:

    • “She looked me in the face and she said… you’re gonna be the best father you could possibly be...And you’re going to keep it.” [36:01]
    • “There is an emptiness that comes with it, because you’re not sure if you’ll ever have that again in life...what offsets it is, my two daughters.” [36:01]

6. Signature Banter and Beef Top Five

• Who Pays for Dinner?

  • Stephen A. jokes nearly nobody ever pays for him—except for his daughters, who know they'll just charge something later anyway. [32:04]

• Top Five Beefs

  • Dan riffs on public feuds; LeBron makes the list, but Stephen A. struggles to see many others as serious personal beefs.
    • Playful mention of Cowboys fans: “I love seeing them cry, though, when they lose. Oh, it brings me such joy.” [40:22]

• Jerry Jones as Face of the NFL

  • “If Jerry Jones had to select between [a Super Bowl or team value]? He would say winning the Super Bowl, I believe it’s being the most valuable franchise. That man is about his money.” [41:33]

Notable Quotes & Memorable Moments

• On Returning After Adversity

  • “Usually when ESPN lets you go, it's a death knell, particularly if you're a black man in this industry...That's a lot to overcome...” [04:56]

• On Fear as Motivation

  • “I am always of the mindset that at the snap of a finger, it can all be taken away from me. That is how I approach my everyday life...” [07:23]

• On Authenticity in Corporate Media

  • “All I've ever encouraged you to do is remember you're not just having to think about you. It's more than just about you.” [10:21]

• On LeBron

  • “He doesn't like me. We don't like each other. It is what it is. And it's probably going to stay that way forever.” [23:10]

• On Jerry Jones

  • “He would say winning the Super Bowl. I believe it’s being the most valuable franchise in football. That man is about his money...” [41:33]

Important Segment Timestamps

| Timestamp | Segment | |---------------|---------------------------------------------------------------| | 01:53 | Stephen A. joins, discusses work and travel | | 04:56 | Stephen A. describes being fired from ESPN and comeback | | 06:32 | Childhood, fear, and drive explained | | 10:21 | Corporate media realities, authenticity, and responsibility | | 14:36 | ESPN’s business changes, NFL ownership, Spike Lee doc | | 23:10 | Relationship breakdown with LeBron James | | 28:30 | Relationships with Shannon Sharpe and Skip Bayless | | 32:04 | Who pays for dinners; stories about Stephen A.’s daughters | | 36:01 | Emotional reflection on his late mother, fatherhood | | 40:22 | Stephen A. on Cowboys fans—favorite sports “beef” | | 41:33 | Jerry Jones’ priorities and face of the NFL |

Tone and Style

There’s a blend of classic Stephen A. bravado, honest self-assessment, competitive bravura, and warm, familial storytelling. The episode is engaging, unafraid of truth, and ultimately generous—a masterclass in both personal and professional resilience delivered with the candor and showmanship only Stephen A. Smith can provide.

End of Summary