Fail Better with David Duchovny

Episode: Fail Again: Chris Evert Hates To Lose More Than She Loves To Win

Date: January 13, 2026
Guest: Chris Evert

Main Theme and Purpose

In this episode, David Duchovny sits down with tennis legend Chris Evert to explore how failure shapes champions—both on and off the court. They delve into the emotional complexity of competition, what it's like to be a trailblazer in women’s sports, and how the shadow of loss, more than the joy of victory, propelled Evert’s iconic career. This intimate conversation touches on childhood, rivalry, shifting identity after retirement, health battles, and the resilience needed to navigate each “failure” along the way.

Key Discussion Points and Insights

1. The Nature of Failure in Tennis

• Solo Sport, Constant Failure:
  • Duchovny frames the conversation around how, even for the greatest, tennis is a sport where losing is ever-present: “The best player of all time… loses 46% of the time. Now, that's obviously not the matches. That's the points.” (04:51)
• Mental Warfare for Female Athletes:
  • Evert observes the 'warrior' mentality required of women in sport, which historically clashes with nurturing expectations:

    “Men have been warriors for centuries and women have not... for us to get out there, I think it really kind of was a little confusing in the beginning… I want to beat this person's brains out, and at the same time, you know, I want to be nice to them.” (05:25)

2. Competing With (and Against) Those You Love

• Family and Friendship on the Court:
  • Evert discusses the emotional toll of playing her sister Jeannie—and the odd relief of being beaten by her:

    “There’s no way I was going to lose to her… I felt so bad for her… On the other hand, there's a match in doubles … we lost in doubles [to her sister], and I... didn't talk to her for three days.” (06:46; 08:14)

  • On suffering public defeat:

    “I hated to lose more than I love to win.” (10:15)
    “Not fun. No fun.” – on losing in the public eye as a teenager. (11:38)

3. Losing, Learning, and Public Identity

• Brand vs. Self:
  • Evert reflects on being constructed as a “tabloid athlete” and the burden of maintaining an image:

    “You are this image. You're in a little bubble and you feel responsible to act within that image... I didn't have the freedom to go out and take chances and figure out who I really was.” (16:07)

• The Pressure of Early Fame:
  • “I think it's just a lot easier for somebody to achieve fame and recognition … in their 20s … then when they're… 10, 11, 12 years old.” (16:43)

4. Emotional Control and Warrior Stoicism

• Masking Emotions for Advantage:
  • On her father’s advice:

    “Don't get mad, because then your opponent will use it to their advantage... Whenever I saw my opponent start to show emotion or get mad, I knew I had them.” (19:49)

• Born with Calm:
  • Evert credits innate temperament and style:

    “I was born with the ability to, you know, be calm, deal with pressure well...” (20:43)

5. On Choking and Resilience

• How Elite Athletes Self-Diagnose Choking:
  • Evert describes her version of choking as passivity and offers practical advice she now gives to young players:

    “Do a body scan of yourself. How are your feet? … Are you making too many errors … or are you too timid? … Over-exaggerate what you're not doing well.” (38:14-40:15)

6. Adapting to Change: Technology and Rivals

• Redefining Her Game:
  • Evert discusses the transition to new racquets and adapting to the rise of Martina Navratilova:

    “I did lose to Martina 13 times in a row, being stubborn and not willing to change anything… But finally I did…” (29:47–31:55)

  • On her rivalry:

    “Marti and I did push each other and we just wanted to keep playing each other… we kind of ended on equal grounds… which is kind of great.” (33:03)

7. On Retirement and the Loss of Spotlight

• Redefining Success Off the Court:
  • Evert explains how motherhood became her new “win” after tennis:

    “No Wimbledon title, nothing compared to being a mom… the most joy I ever felt in my life.” (43:36)

  • She discusses the burn-out and emotional transition:

    “I started feeling like I didn't want to get out of bed and go play a match. I just, I had it mentally so I was ready, I was ready to retire.” (44:22)

8. Failing as a Broadcaster—At First

• New Arena, New Failures:
  • Evert is candid about her struggles in her first broadcasting stint:

    “I was a great player. I'm going to be great at this... But you know, that's not good for commentating to keep it simple. Everyone wants to know, you know, the details…” (47:49–48:44)

  • On returning better equipped years later:

    “By that time, I had been coaching my academy kids… so… I said, okay, I'll try it for one week. … It's been like 15 years I've been with [ESPN] since then.” (49:53–50:54)

9. Illness, Mortality, and Spiritual Growth

• Facing Cancer—Twice:
  • Evert opens up about her battles with cancer and her perspective:

    “I just... realized that I'm one of millions… I felt like, why not me? … I had a better attitude... My body's always been strong as an athlete… I kind of lost that going through the chemo…” (51:56–53:12)

  • On Information and Prevention:

    “There's a big difference between stage one, getting something early than stage four or five… that's the difference between life and death.” (54:33)

• Spirituality in Later Life:
  • On searching for connection and meaning after facing mortality:

    “You become more spiritual and I've become closer to my higher being... I want to have more of a connection to my higher power.” (55:48–56:41)

Notable Quotes & Memorable Moments

• “I hated to lose more than I love to win.” — Chris Evert [10:15]
• “You are this image... I didn't have the freedom to ... figure out who I really was.” — Chris Evert [16:07]
• “Whenever I saw my opponent start to show emotion or get mad, I knew I had them.” — Chris Evert [19:49]
• “I did lose to Martina 13 times in a row, being stubborn and not willing to change anything... But finally I did.” — Chris Evert [29:52]
• “Nobody beats Vitas Gerulaitis 14 times in a row.” — (referencing the famous quote, attributed to Gerulaitis) [34:38]
• “No Wimbledon title, nothing compared to being a mom.” — Chris Evert [43:36]
• “I felt like, why not me? ... it's almost normal.” — Chris Evert on cancer [51:56]
• “Make it simple. Like I do everything else in life.” — Chris Evert [57:34]

Timestamps for Key Segments

• [05:25] — Evert on the contradictory aggression and nurture in women’s sports
• [08:14] — Losing to her sister and her own reactions to failure
• [10:15] — The hatred of losing as motivation
• [16:07] — Navigating the “image” and public perception
• [19:49] — Masking emotions as competitive strategy
• [29:47] — Adapting after being overtaken by Martina Navratilova
• [34:38] — “Nobody beats Vitas Gerulaitis 14 times in a row.”
• [38:14] — Evert’s ‘body scan’ advice on pressure and choking
• [43:36] — Motherhood vs. athletic glory
• [47:49] — Failing as a broadcaster after retiring
• [51:56] — On her cancer diagnosis and resilience
• [54:33] — The importance of early diagnosis
• [55:48] — Facing mortality, turning inward to spirituality

Tone and Style

The conversation is candid, self-effacing, and frequently introspective. Both Duchovny and Evert blend humor with vulnerability, and the tone remains respectful, warm, and insightful throughout.

Takeaways for Listeners

• Even at the summit of success, failure is constant and indispensable to growth.
• Public images often obscure the complexity and private struggles of champions.
• Adaptation—whether to rivals, technology, or life after fame—is the mark of enduring success.
• True resilience often comes from confronting, not fleeing, discomfort, loss, and failure.
• Identity and self-worth are constantly negotiated, not fixed, no matter how great the accolades.
• There’s meaning and healing in moving beyond “athletic toughness” to emotional honesty and spiritual inquiry.