The Player’s Box

Episode 23 | Australian Open 4th Round Preview — Madi vs. Jess
Release Date: January 25, 2026
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

This playful, high-energy episode is a mini preview ahead of the highly anticipated Australian Open fourth-round match between co-hosts Madison Keys and Jessica Pegula. The group dives deep into the unique scenario of podcast co-hosts facing off on such a big stage, looking back at their shared history, sharing insider tennis banter, and engaging in lighthearted debates and games. Personal stories, trash talk, and a series of fun “who’d be better at” questions give fans a peek behind the competitive curtain into the genuine camaraderie among four of the tour’s most beloved players.

Key Discussion Points & Insights

1. The Big Matchup: Keys vs. Pegula at the Australian Open

• (01:10) Jenny Brady kicks things off by asking both Madison and Jess for their take on the match-up.
  • Madison Keys:
    • Recalls their previous matches, specifically referencing their tightly contested Adelaide final.
    • Praises Jess for her relentless consistency:

      “She’s just always like winning. She’s always there. She’s just everywhere.” — Madison Keys (01:50)

    • Shares a humorous story about how she described her streak of quarterfinals as being in her “Pegula era.”
  • Jessica Pegula:
    • Remembers last year’s Adelaide final, how impressive Maddie’s form was, and their group chat predicting her Australian Open win:

      “Once I was kind of out of the tournament, that was when Jenny, Dez and I were all texting that she was getting through all these tough matches and...we thought she was gonna win Australian Open, and she did.” — Jess Pegula (02:43)

    • Expresses hope that Keys doesn’t bring that level against her this time:

      “Tomorrow, like, she can not play that level. It'll be great.” — Jess Pegula (03:16)

2. Friendly Rivalry & Tactical Banter

• (03:24) Light-hearted banter about signature moves and nerves:
  • Pegula jokes about watching out for Keys' forehand “hack.”
  • Keys admits to scouting Pegula’s last match, delighting in a flubbed slice:

    “You missed a hack slice forehand, and you were so annoyed, and I was like, heh, heh, heh.” — Madison Keys (03:50)

  • Both agree they might burst out laughing if these moments come up in the actual match.

3. Their First Encounters: Early Days on Tour

• (04:41–10:56) The group gets nostalgic as Jess and Maddie recount early run-ins as teenagers, their very first matches, and their diverging junior careers:
  • Pegula can't remember their true first meeting, but both recall playing as teenagers at a Ponte Vedra event and later at Indian Wells pre-qualifying.
  • Keys reflects on jumping into pro tournaments at a young age, quickly rising through the ranks, while Pegula shares her struggles with injuries and her circuitous climb to the top 100.

    “I feel like Maddie was like touted so much ... I think I probably lost the match before I even walked on the court.” — Jess Pegula (08:00)
    “I started playing like, the challengers and stuff, like I kind of moved up the rankings fairly quickly ... and I felt like at that time, like, you would come back from injury or something, and you'd have, like, a great couple of months, and then you’d be out again.” — Madison Keys (09:10)

4. The ULTIMATE Friendly Wagers

• (11:56) Trash talk and terms of a friendly bet for the match’s loser:
  • If Madison loses: She must eat cheese on apple pie (Pegula’s favorite combo).
  • If Jess loses: She must wear a Kansas City Chiefs jersey (rival NFL team to Pegula’s family-owned Buffalo Bills).

    “My family owns the Buffalo Bills... mine's definitely worse.” — Jess Pegula (12:29)

  • Madison ups the ante, proposing the loser should also wear Taylor Swift bracelets, and perhaps even a Taylor Swift shirt, combining the NFL rivalry with pop culture references.

    “I wanted the chief’s jersey with like a whole stack of... Taylor Swift friendship bracelets.” — Madison Keys (13:57)

5. “Who’s Most Likely To...” — Game Segment

• (14:55–19:25) Jenny and Dez play a rapid-fire game, guessing which of Maddie or Jess would excel at various off-court scenarios, providing hilarious and revealing moments:
  • Example categories and consensus:
    • Better at Real Housewives: Maddie
    • Crying convincingly on camera: Maddie
    • Becoming a fan favorite: Both
    • Winning shop til you drop: Maddie
    • Talking way into a free upgrade: Jess
    • Losing receipt immediately: Jess
    • Impulse buying something unnecessary: Maddie
    • Talking way out of a speeding ticket: Jess
    • Burying a (fictional) dead body: Maddie (“She's ride or die.” — Jenny Brady, 17:59)
    • Keeping a straight face in a crisis: Maddie
    • Assembling IKEA furniture: Maddie
    • Handling an adult meltdown: Jess
  • Brief, light-hearted bickering ensues as Maddie and Jess chime in—often being shushed!

Notable Quotes & Memorable Moments

• On their “Pegula era” friendship:

  “I was like, I’m in my Pegula era. I just quarter every week all of a sudden.” — Madison Keys (01:55)

• On the playful rivalry:

  “If I get you on any of them, I might just, like, immediately start laughing.” — Madison Keys (04:18)  “I think I’m going to start laughing, take... Depending on the score, or I’m going to take the ball and be like, this effing slice forehand.” — Jess Pegula (04:29)

• On the pain of the potential bet:

  “Cheese on apple pie is pretty brutal.” — Madison Keys (12:27) “My family owns the Buffalo Bills. I have to sit there and wear this... people are gonna be like, Jess clearly lost a bet and I’m gonna have to suffer.” — Jess Pegula (12:29)

• On early-career flashbacks:

  “I remember when we played that match, I think I probably lost the match like before I even like walked on the court. Although I think it was close.” — Jess Pegula (08:00)

• Who would help you cover up a crime?:

  “She’s ride or die.” — Jenny Brady (17:59)

Important Timestamps

• 01:10 — Preview and mutual breakdown of the upcoming fourth-round match (Maddie and Jess)
• 04:41–10:56 — Pegula and Keys reminisce about their first encounters and junior tour memories
• 11:56 — Trash-talk segment and friendly bet: cheese on apple pie vs. Chiefs jersey (plus Taylor Swift twist)
• 14:55–19:25 — “Who’s Most Likely To...” game with Jenny and Dez, featuring a range of funny superlatives

Tone & Takeaway

The episode is candid, cheeky, and full of inside jokes, giving listeners a rare, entertaining glimpse of elite athletes’ friendships and pre-match rituals. Rather than deep technical breakdowns, the focus is on personality, history, and joy in competition. The stakes aren’t just about advancing at the Australian Open—it’s also about pride, banter, and who will have to endure the greatest off-court embarrassment.

Fans will come away not only more invested in the match but also feeling part of the tight-knit community and vivid personalities that make up The Player’s Box.

Closing Moment:

“Well, good luck to you both. Please leave us a rating and review... and may the odds be ever in your favor.” — Jenny Brady (19:52)

“Wow. That was an unhinged episode.” — Jess Pegula (20:24)