The Player's Box

Episode 14 | Tennis Headlines, Most Likely To & Who Am I

Release Date: November 25, 2025

Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

In this lively and humorous episode, Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk deliver their unique takes on tennis headlines and behind-the-scenes tour life. The quartet kicks off with “Unforced Error/Winner of the Week” confessions, discusses trending tour stories (retirements, post-season travel, and tennis Twitter oddities), and plays several games (“Most Likely To” and “Who Am I?”). The episode also features candid discussions about fertility, the struggles of post-tennis life, and plenty of unfettered banter enhanced by their close friendship.

Key Segments & Discussion Highlights

1. Unforced Error/Winner of the Week

[00:48–08:13]

• Jenny's (Brady) Unforced Error:

  • Wore compression socks to a bachelorette/bridal shower, slipped on stairs, landed on her butt. “The compression socks are really slippery... I land, like, on my butt...” (01:58)
  • Desirae quickly puts down a stair runner: “I was like, that is a lawsuit waiting to happen.” (03:24)

• Madison's (Keys) Winner:

  • Avoided jury duty last minute, gaining a “free” day:
    • “I got an email, and they said, we don't need you. You're dismissed. We will not contact you for 12 more months at least.” (04:02–04:25)

• Desirae's (Krawczyk) Winner:

  • Finished her egg freezing injections:
    • “I’m officially done with my injections, so yay me.” (04:40)

• Jess's (Pegula) Unforced Error:

  • Waited almost an hour for a haircut at a new place but ultimately stayed:
    • “He was 52 minutes late... But he did a good job and I got a good haircut.” (05:49)
  • Admits she would’ve done nothing about it:
    • “I still tipped him. I paid full, made zero effort to... dispute the fact that I sat there.” (06:45)

Memorable moment:
Jenny and Desirae bicker over who wins “Winner of the Winners” and “Unforced Error” accolades, all delivered with their signature self-deprecation.

2. Tennis Tour Headlines

[09:01–14:18]

• Maldives Off-Season FOMO:

  • All four hosts have never been, but note it’s the trendy tennis player destination:
    • “Every year everyone goes except for us.” (11:04)
  • Speculation on why: sponsorship, free trips for social posts, European convenience.
  • Jess: “Definitely none of the Americans go. Although... Taylor Fritz... has gone.” (12:41)
  • Wonder if anyone ever actually sees each other there:
    • “I want to know if any of them have seen each other there. They for sure [are] at the same resort.” (13:48)

• Tour Banter:

  • Jenny is scandalized at being blamed for loud typing:
    • “I am typing right now. Can you hear me?” (12:01)

3. Real Talk: Egg Freezing Journey

[14:18–18:29]

• Desirae Krawczyk details her egg freezing process:
  • Discusses the injections, procedure, and the importance of open discussion:
    • “The more you talk about it, I think more women... will be more comfortable about it.” (15:42)
    • “If you have the funds... it’s an insurance policy... why not? If you can do it, you don’t want to regret it later.” (16:03)
  • Shares honest symptoms and emotional ups/downs, encourages listeners:
    • “Honestly, it’s like... I don’t have any regrets. I hope other women and other girls... find some sort of courage to do it.” (17:37)

4. Notable Retirements: Chris Eubanks & Lauren Davis

[18:30–24:07]

• Chris Eubanks:
  • Left the tour at 29 after wrist injury and career highs.
  • Transitioning to commentary: “He’s really good at that.” (20:42)
• Lauren Davis:
  • Retires at 32, reflects on tennis and “the next chapter.”
  • “We play tennis our whole lives... and all of a sudden it’s like, okay, you stop and... you’re still young.” (20:14)
• Discussion of ‘Success’ in Tennis:
  • Jess: “Fans get this perception... if you’re not winning all these Grand Slams... your career was a failure... He had an incredible career.” (20:54)
  • Madison: “Players and fans... have a skewed perception... People winning 20 Grand Slams... that’s insane. It’s like, wow, you never made a final? Well, you also did all these other things...” (22:30)
• Andy Murray Reference:
  • Desiree recalls Murray's regret: “He wished he enjoyed his career more... he was too invested in chasing this, chasing that, and not enjoying the moments.” (23:19)

5. Ostapenko’s Instagram Marketplace

[24:54–28:28]

• “Yelena’s Marketplace”
  • Ostapenko’s side hustle selling everything from vacuums to perfume on Instagram,
• Group reactions:
  • Jess: “I’m... flabbergasted. But we respect it, girl’s just trying to get her bag.” (25:28)
  • Madison: “Maybe that’s what paid for the Maldives vacation.” (27:28)
  • Suggest she should expand to represent other player’s stuff:
    • “She should literally... all of us can bring stuff and be like, can you sell this for me?” (28:05)

6. Game Segment: Most Likely To… (On/Off Court)

[28:28–36:44]

A. Among Themselves (Hosts Only)

• On Court

  • Saving Match Points: Madison
  • Most Improved: Jenny
  • Most Mentally Tough: Jess
  • Most Superstitious: Des or Jenny
  • Physio Addict: Des
  • Practice After Win: Jess
  • Snacking on Changeovers: Jenny/Des
  • Lingering in Gym: Jenny (“Even if she’s not working out!”)

• Off Court

  • Always Late to Dinner: Jess
  • Restaurant Guru: Jenny
  • Most Stylish: Des
  • Messiest Packer: Des
  • Most Dog-Obsessed: Des (while her dog is on her lap on the podcast)
  • Most Likely to Say Something Controversial/Become a Meme/Roast Themselves: Jenny
  • Most Likely to Nap Anywhere/Explore Cities on Foot: Des
  • Most Likely to Start Beef (Jokingly/Not): Jenny

Notable Quotes:

• “Jenny, starting beef would be like, ‘I hate you’... next day, ‘How’s the family?’” – Madison (32:51)

B. Wider WTA Tour

[38:48–44:00]

• Mentally Tough: Coco Gauff, Sabalenka
• Superstitious/Routines: Iga Swiatek
• Grinder in Gym: Maria Sakkari (“She’s jacked...practices 8 hours a day.”)
• Stylish: Sabalenka, “the Asians,” Coco Gauff, Marta Kostyuk
• Late to Dinner: Jess or Frances Tiafoe (“That’s why we tell them to come 15 minutes before.”)
• Dog-Obsessed: Anna Kalinskaya, Marta Kostyuk, Anastasia Potapova

7. Contact Photos and Group Chat Insights

[36:44–37:47]

• Laughter over the disastrous contact photos each one has for the others (including a photo of Jenny with a COVID swab up her nose or Jess “growing wings”).
• “Should we talk about Maddie’s contact photos for all of us?” – Des
• Friendly teasing and inside jokes about their group dynamics.

8. Who Am I? – Guess the Player Game

[44:50–47:26]

• Jess runs a cryptic “Who am I?”:
  • “Her name suggests a sudden flash. She has played Call of Duty before. I vote for this girl every year for the sportsmanship award, but she doesn’t win it.”
  • Listeners are invited to comment their guesses.

9. Fan Q&A

[47:28–59:14]

• Olympic Qualification Process:

  • Madison: “To qualify... eligible to play three of the Billie Jean King Cup ties... top four singles, two doubles, two mixed.”
  • Jess adds: “For doubles... there’s a site entry list [for mixed].”

• TikTok Activity:

  • “I get tight posting things... After I posted that one… it went viral and was just people making fun of it.” – Jess (49:59)
  • Group agrees they need a podcast TikTok for shared posts.

• Friendship Origins:

  • “We were all tight with Jenny before that... once this chat started and podcast... we bonded.” – Des (53:39)
  • “Maddie’s definitely the hardest to break down.” – Jess (55:25)
  • “I’m easy!” – Jenny

• Headphones Hate for Jess:

  • She uses old-school wired headphones, which viewers regularly mock in comments:
    • “These headphones have been the only reliable piece of equipment...”
    • “My trainer told me the Bluetooth is melting my brain... so now I'm kind of listening to him.” (57:13, 58:49)

Notable Quotes & Moments

• On redefining success in tennis (Madison):
  “Players and fans... have a skewed perception... people winning one Grand Slam is something you dream of as a kid... the fact that there are people winning 20, now it’s like, ‘Wow, you never made a final?’” (22:30)

• On egg freezing journey (Desirae):
  “Honestly, it’s like, I don’t have any regrets. I hope other women... find the courage to do it...” (17:37)

• Maldives travel envy (Jess):
  “Every year everyone goes except for us.” (11:04)

• On Ostapenko’s Marketplace (Jess):
  “Girl’s just trying to get her bag... it’s kind of awesome.” (26:13, 26:17)

• Game Show Banter (Jenny):
  “‘Jenny, starting beef would be like, ‘I hate you,’ and the next day, ‘How’s the family?’” – Maddie (32:51)

Structure & Tone

The podcast is fast-paced, self-deprecating, and full of inside jokes born out of years on tour and close friendship. The hosts offer genuine reflections on tennis beyond competition—retirements, aging, fertility, mental health, fame, and friendship.

Timestamps Quick Reference

• Unforced Errors & Winners: 00:48–08:13
• Maldives FOMO/Headlines: 09:01–14:18
• Egg Freezing Insights: 14:18–18:29
• Retirements & Tennis Culture: 18:30–24:07
• Ostapenko’s Marketplace: 24:54–28:28
• Most Likely To (Hosts): 28:28–36:44
• Most Likely To (Tour): 38:48–44:00
• Who Am I?: 44:50–47:26
• Fan Q&A: 47:28–59:14

The Player's Box continues to shine as a candid, funny, and occasionally heartfelt look at the real lives of WTA players, balancing lighthearted games with real talk on everything from career changes to women’s health. For listeners wanting the real behind-the-scenes tennis experience, this episode is both insightful and entertaining—“your all-access pass to life beyond the baseline.”