The Player's Box cover

The Player's Box

Keys, Pegula, Brady, Krawczyk

Think you know your favorite athletes? You’ve seen them on the court, but what about the mishaps, late nights, and unexpected encounters that happen before the game starts? Step inside the world of tennis with Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk as they pull back the curtain on life behind the scenes. From breaking down the game to sharing wild travel stories, pop culture takes, and plenty of fan Q&As, it’s your all-access pass to life beyond the baseline. The Players Box drops every Tuesday—grab your seat courtside.

Think you know your favorite athletes? You’ve seen them on the court, but what about the mishaps, late nights, and unexpected encounters that happen before the game starts? Step inside the world of tennis with Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk as they pull back the curtain on life behind the scenes. From breaking down the game to sharing wild travel stories, pop culture takes, and plenty of fan Q&As, it’s your all-access pass to life beyond the baseline. The Players Box drops every Tuesday—grab your seat courtside.

64 | Love is Blind Stay or Run & Advice Updates

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Episodes

64 | Love is Blind Stay or Run & Advice Updates 03 Nov 2026

This week on The Player’s Box, we uncover some surprising opinions like who thinks a mattress on the floor with absolutely no other furniture is a green flag, and who is perfectly fine with their significant other going days without texting back. At least we all agree on social media etiquette, including exactly how many people is too many to follow before it becomes a red flag. And, of course, we’re all doing gorgina. Don’t forget to grab your merch before the 8th! https://theplayersboxpodcast62026.itemorder.com/shop/home/ Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

63 | Multitasking, Meltdowns & What’s the Password 27 Oct 2026

This week on The Player’s Box we learn that competition doesn’t stop at the court because fights ensue over a simple game of Password. Plus, we find out who can multitask, who can’t remember texts they sent an hour ago and who gets so distracted they end up just standing at the fridge. Grab your merch here! theplayersboxpodcast62026.itemorder.com/shop/home Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod - Cure - Go to https://curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

62 | Home Screens, Guess the Celeb & Rants 20 Oct 2026

This week on The Player’s Box, the Guess my Number game went so well (poorly) that we attempted to play again by assigning each person a celebrity and it went about as well as you would expect (chaotically). Plus, we’re exposing everyone’s iPhone home screens: who has 6 pages of apps, whose is color categorized, who has an un-downloaded Seat Geek app front and center and whose screen saver came with the phone. Plus tennis headlines, a new rant and more. Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod - Cure - Go to https://curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

61 | Halloween Trivia & Tennis Headlines 13 Oct 2026

This week on The Player’s Box we’re down a Des again (hopefully for the last time), we learn Jess and Jenny do not know Halloween trivia nor what a witch sounds like while Madi is basically Queen of the season, we cover tennis headlines and end on a very hot take about TV from Jenny. Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

60 | Google Search History & Rants 06 Oct 2026

This week on the Player’s Box we lose Des to bad WiFi, investigate everyone’s recent Google search history (shockingly on brand) and introduce a segment of rants where we learn the pod ranges from "Alexa is always listening" to full pro-robot. Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

59 | What’s My Number & Sweater Weather 29 Sep 2026

This week might be one of the most chaotic weeks in Player’s Box history. Someone needs to run Jenny through concussion protocol, Jess is gaslit, Madi is offended and Des is up too early for this nonsense. Also, tennis headlines, fall favorites and some low stakes advice. Thank you to our sponsors: - Quince - head to https://quince.com/playersbox for free shipping on your order and 365 day returns - Cure - Go to https://curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX. - OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at https://oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

58 | US Open Fines & More from History 22 Sep 2026

This week on The Player’s Box ice cream melted, someone tried to fill up an electric car with gas, someone got burned and someone lingered. You be the judge! We also discuss all of the recent US Open fines plus the biggest fines from tennis history. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

57 | US Open Wrap Up & Home Design 15 Sep 2026

This week on The Player’s Box Jenny has car karma, go to Jess if you’d like museum tickets she probably has extra, Des attempted an art project and Madi is living in windshield final destination. Plus, a US Open wrap up, Madi was in Architectural Digest and we learn about everyone’s homes. Grab our new merch before the store closes on 9/20! Purchase here: https://theplayersboxpodcast52026.itemorder.com/ Thank you to our sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns Cure - Go to curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX Bilt - Download the Bilt app and join membership for where you live at joinbilt.com/playersbox OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

56 | Josh Allen in The Player’s Box & US Open Updates 06 Sep 2026

In honor of football Sunday, we’re dropping this episode a little early. The entire Player’s Box team pulled off the surprise of the podcast bringing Josh Allen in to surprise Jenny. Everyone panics, Jenny is confused and then we recap how we pulled it off. Also, Josh plays some tennis trivia, goes through girl dad training camp and gives us his own UFE. Then we give some US Open updates. Grab our new merch before the store closes on 9/13! Purchase here: https://theplayersboxpodcast52026.itemorder.com/ Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

55 | Live from New York: US Open, NYC Bucket List & Confessions 01 Sep 2026

The Player’s Box is live this week to kick off the US Open and half the pod almost didn’t make it since Jenny’s plane almost ran out of fuel (at least it wasn’t a car) and Des sat at the wrong gate for the wrong delayed flight. Jess has a live Unforced Error while Madi’s match was used as someone’s personal remote office. Plus, tennis headlines and best US Open and NYC memories. Thank you to our sponsor and host for this episode, World of Hyatt, a loyalty program designed to reward members with hotel stays, benefits, and curated travel experiences. This collaboration gives listeners access to premium, money-can’t-buy experiences that feel exclusive, memorable, and uniquely tailored to fans who value exceptional travel. For more information or to join World of Hyatt, please visit world.hyatt.com Purchase our most recent merch drop here: https://theplayersboxpodcast52026.itemorder.com/ Thank you to our other sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns Cure - Go to curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX. Amazon Health AI - Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Bilt - Download the Bilt app and join membership for where you live at joinbilt.com/playersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

54 | Cincinnati Open & One Year of The Player’s Box 25 Aug 2026

This week we walk down a year of memory lane on the pod with Jenny’s bloopers, Madi’s anti-lingering, Jess’s tech issues and Des trying to get us cancelled and yet we’ve never missed an episode. Also, Cincinnati Open and more tennis headlines. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Thank you to our other sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns Cure - Go to curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX. Square - Get up to $200 off Square hardware when you sign up at square.com/go/playersbox Bilt - Download the Bilt app and join membership for where you live at joinbilt.com/playersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

53 | Cincinnati Open, Queen City & Fan UFEs 18 Aug 2026

This week on The Player’s Box we’re just going to stop letting the group chat leave the house because there’s food spilled all over the grocery store, drinks spilled on themselves, Ubers hitting objects on highways and cancelled flights. The luck is not with the group. Plus, Cincinnati Open updates and some games for the Queen City. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more If you want to leave us a voicemail, join us over on Patreon at https://patreon.com/theplayersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

52 | Toronto Updates & Canada Games 11 Aug 2026

This week on The Player’s Box Madi received the world’s most expensive pack of Clorox wipes, Jess returns to the Florida DMV (iykyk), and Jenny gives Des a new last name. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more If you want to leave us a voicemail, join us over on Patreon at https://patreon.com/theplayersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

51 | Tennis Updates & What’s Streaming 04 Aug 2026

This week on The Player’s Box we are anti-slipper as they caused Jenny to get strep throat and Jess to step on glass. Madi was ready to call anyone and everyone involved in a recent documentary and Des bought a puzzle that was 80% sky. Plus, some tennis updates, upcoming tournaments, and thoughts on true crime documentaries. If you want to leave us a voicemail, join us over on Patreon at https://patreon.com/theplayersbox Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

50 | Memphis and DC Tournaments & Trivia 28 Jul 2026

This week on The Player’s Box Jenny is in a club with slippers, Des killed all of her plants, Jess lost multiple iPad cases multiple times and Madi didn’t sleep for basically two full days. Everyone is doing great. Also, tennis-ish headlines and some Memphis and DC based trivia in honor of the tournaments this week. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Thank you to our other sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns Cure - Go to curehydration.com/playersbox and get 20% off your first order with promo code PLAYERSBOX. Square - Get up to $200 off Square hardware when you sign up at square.com/go/playersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

49 | Never Have I Ever & Summer Memories 21 Jul 2026

This week on The Player’s Box Des is a reckless child while Jenny has no tolerance for her reckless ways, Jess hate deleted her own Instagram comment (or did she…) and Madi has created a hugo spritz monster. Also, never have I ever, summer memories and next tournaments. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

48 | Wimbledon Week Two & Wedding Stories 14 Jul 2026

This week on The Player’s Box, we hope Des’s car rental company doesn’t listen to the pod, TBD if Jenny knows the time for our next recording, Madi is her own task rabbit, and Jess had quite the welcome home. Also, Wimbledon week two and wedding stories. Thank you to our episode sponsor, Amazon Health AI. Amazon Health AI can connect your symptoms with your medical history and it can even get you care, 24/7. Learn more at: https://health.amazon.com/prime/onemedical/membership/health-ai/learn-more Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

47 | Wimbledon Week One, Live Show Recap & Red Cards 07 Jul 2026

This week on The Player’s Box, we recap our live event last week where Madi had a food related meltdown, Des and Jenny had a sister moment in public and Jess nailed the hardest name known to man. And something happens to someone in a car, probably. Also, Wimbledon week one, and red and yellow cards. Our merch is still live! Go to theplayersboxpod.com and grab yours now. Patreon members get a special 10% off code, so sign up there at Patreon.com/theplayersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

46 | Live from London: Wimbledon, Taste Tests & Traditions 30 Jun 2026

This week on The Player’s Box Jess and Des had an upsetting symphony behind them during Phantom of the Opera, Madi is going to handle the group dinner planning and the podcast team will be buying Jenny a bus pass and confiscating her keys. Plus, taste testing pastries, the grass court season and proper or problematic Wimbledon traditions. Thank you to our sponsor and host for this episode, World of Hyatt, whose loyalty program is designed to reward members with hotel stays, benefits, and curated travel experiences. This collaboration gives listeners access to premium, money-can’t-buy experiences that feel exclusive, memorable, and uniquely tailored to fans who value exceptional travel. For more information or to join World of Hyatt, please visit world.hyatt.com Our merch is now live! Go to theplayersboxpod.com and grab yours now. Patreon members get a special 10% off code, so sign up there at patreon.com/theplayersbox Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

45 | Out of Context Texts & Grass Court Season 23 Jun 2026

This week on The Player’s Box we learn Jess’s other job for the pod, Madi’s passion for the Super Bowl, why the entire group chat turned on Des and whether Jenny is a good singer. Also, all of the recent tennis headlines of the week. To see more out of context texts, plus bonus content and ad-free listening, head to Patreon.com/theplayersbox Thank you to our sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

44 | Hannah Berner in The Player’s Box 16 Jun 2026

This week on The Player’s Box Jenny invites strangers into the bathroom, Madi’s legal at the DMV again but now has no air in her tires, Des comes to us mid-recording from the locker room and Hannah and Jess are lifelong doubles partners. Plus, Hannah’s tennis journey and all about her new Hulu special, None of my Business. Thank you to our sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

43 | Roland Garros Week Two & More Headlines 09 Jun 2026

This week on The Player’s Box Jess is a brand rep for the Florida DMV while simultaneously the DMV seems to think Madi is a bot, if you see Jenny trying to break into your car get in line, and Des opted for a bike amongst football chaos. This podcast is not sponsored by the DMV or automobiles. Also, Roland Garros week two, tennis headlines, and an update from Jenny. Thank you to our sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Omaha Steaks - Get flavorful, high-quality proteins delivered by visiting omahasteaks.com plus $35 off when you use promo code PLAYERSBOX Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

42 | Roland Garros Week One & Rank and Reveal 02 Jun 2026

This week on The Player’s Box Des and Jenny’s hypothetical celebrity dreams come true, headphones couldn’t save Jess from flying with the world’s most annoying couple and Madi resumes her role as our featured Bravo historian. Also, Roland Garros week one headlines and we play Rank and Reveal for some dream scenarios. Be sure to check out all of our sponsors at: https://www.theplayersboxpod.com/ Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

41 | Live from Paris: Roland Garros & Travel Days 26 May 2026

This week on The Player’s Box we’re live from stage and a TV where we learn that Madi won’t even glamp (it’s still outdoors), Jenny was asked to not return to French class, don’t come between Jess and her breakfast and Des not only travels with a full living room but also 11 toiletry bags. Thank you to our sponsor and host for this episode, World of Hyatt, whose loyalty program is designed to reward members with hotel stays, benefits, and curated travel experiences. This collaboration gives listeners access to premium, money-can’t-buy experiences that feel exclusive, memorable, and uniquely tailored to fans who value exceptional travel. For more information or to join World of Hyatt, please visit world.hyatt.com. Please join us over on Patreon for The Player’s Box Social Club with ad-free and exclusive bonus content at patreon.com/theplayersbox Thank you to our other sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Huel - Get Huel today with our exclusive offer of 15% off online with code PLAYERSBOX at huel.com/PLAYERSBOX Omaha Steaks - Get flavorful, high-quality proteins delivered by visiting omahasteaks.com plus $35 off when you use promo code PLAYERSBOX Warby Parker - Buy one prescription pair of glasses and get 20% off any additional prescription pairs at WarbyParker.com/PLAYERSBOX Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

40 | Tennis Updates & Top 5 Horror Movies 19 May 2026

This week on The Player’s Box we learn everything not to do if you want to stay on the pod’s good side, including sending Jenny a voice memo with words, FaceTiming Jess, giving Madi a bad dessert, and asking Des “hey can you talk?” Also, tennis headlines of the week, our Top 5 Horror Movies and more low stakes advice! Please join us over on Patreon for The Player’s Box Social Club with ad-free and exclusive bonus content at patreon.com/theplayersbox You can find a list of our sponsors with promo codes at theplayersboxpod.com Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

39 | Italy, Iconic Movies & Met Gala 12 May 2026

This week on The Player’s Box Des wants a ball gown-y dress, Jenny invents an incredible new phrase, Jess supports announcing an Irish goodbye, and nothing is coming between Madi and Pretty Woman. Also, we play this or that with iconic movies, determine which Italian dishes are real or fake and give some more low stakes advice. Thank you to our sponsors: Quince - head to quince.com/playersbox for free shipping on your order and 365 day returns OneSkin - Get 15% off OneSkin with the code PLAYERSBOX at oneskin.co/playersbox #oneskinpod Warby Parker - Buy one prescription pair of glasses and get 20% off any additional prescription pairs at WarbyParker.com/PLAYERSBOX Huel - Get Huel today with our exclusive offer of 15% off online with code PLAYERSBOX at huel.com/PLAYERSBOX Omaha Steaks - Get flavorful, high-quality proteins delivered by visiting omahasteaks.com plus $35 off when you use promo code PLAYERSBOX Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

38 | Rome, Pet Peeves & Low Stakes Advice 05 May 2026

This week on the Player’s Box Des has some Rome adventures for the ages, Madi’s alive and thriving with her nightly gelato, Jenny is back in the car remembering Iggy and an app is bullying Jess. Also, tennis headlines of the week, our European pet peeves and a look ahead to Rome. You can find a list of our sponsors with promo codes at theplayersboxpod.com Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

37 | Madrid Open, Spring Cleaning & Hallelujah 28 Apr 2026

This week on The Player’s Box the group decides Jess would be great on reality TV, Des accidentally broke into a stranger’s room, Madi’s back to slandering the wilderness and Jenny hit her head again…anything can happen in this episode! Plus, a recap of Madrid, headlines of the week and some great fan questions. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

36 | Tennis Headlines, Horoscopes & Europe 21 Apr 2026

This week it's Jenny and Des vs. modes of transportation as Jenny is back to causing chaos in her car and Des had to sprint through an airport to rescue a lost item. Meanwhile, Jess had a nail emergency and Madi brings an important spelling question to the pod debate floor. Also, tennis headlines, the group reads their horoscopes and a look forward to Europe! Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

35 | Charleston Champions Corner, The Hot Seat & Europe 14 Apr 2026

This week we put Jess, Jenny, Madi and Des in the hot seat and we see what secrets they’re willing to reveal. Jenny does not like what The Rock is cooking, Jess was dared to send a flirty voice note, Des got scammed out of Sumo wrestling and Madi reignites her feud with the airline security who stole her gut string. Also, Jess and Des are Charleston Open winners, tennis headlines and what’s next. Don't forget a limited edition crewneck is available through April 19th! Grab it here: https://theplayersboxpodcast22026.itemorder.com/shop/home/ Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

34 | Charleston Open, Clay Season & Reality TV 07 Apr 2026

This week on The Player's Box Des has our first ever live Unforced Error, Jess has a no bottoms moment (iykyk), someone in Europe is living with Jenny's identity and Madi performs a state of the union on Bravo drama. Also, an overview on the transition to clay season and all of the tennis headlines of the week. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

33 | Alex Eala in The Player’s Box 31 Mar 2026

This week we have a very special guest on The Player’s Box - Alex Eala! We also have a new host, Medison Cues, Jenny continues to catch lingering accusations, meanwhile Jess and Des decided to decorate Jess’s floors with a sea salt latte and Alex parle bien français? Also, we get to hear about Alex’s life growing up, her Philippines travel recommendations and we play a couple games to get to know her better. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

32 | Miami Open Week One 24 Mar 2026

This week on The Player’s Box Jenny basically moved into the Miami Open site, Jess brings us some gossip from the parking lot, Madi was signing body parts and Des accidentally got into a low speed car chase with the cops? Also, all of the insights from the Miami Open so far. Don’t forget merch is back! Grab it here by March 29th! https://theplayersboxpodcast2026.itemorder.com/shop/home/ Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

31 | Miami Open Memories & Indian Wells Headlines 17 Mar 2026

This week on The Player’s Box Jenny used to love a Miami club, Madi agrees to willingly go for a run outside, Jess autographed her own wedding picture and Des is seconds away from being gifted a froze all day t-shirt. Also, a look back at the headlines as Indian Wells wrapped up, and a look ahead at the Miami Open. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

30 | Indian Wells Update, Combined 1000s & Sam Querrey Joins 10 Mar 2026

This week on The Player’s Box Jenny has a lot of superstitions specifically about towels, Madi almost missed a practice due to a sarcasm error, Des really wants you all to comment in the comments and Jess accidentally posted an X rated sponsor to promote the podcast. Also, all things Indian Wells and Sam Querrey joins to discuss Nothing Major’s Hottie Coaches Bracket. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

29 | Indian Wells Memories, Headlines & More 03 Mar 2026

This week on The Player’s Box Madi is LIVID, Des hit Andy Roddick with a flag, Jess joined an 8pm recording at 7pm and Jenny is coming to us live from the back seat of a rental car. Also, tennis headlines and a look back at the best Indian Wells memories. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

28 | Dubai Recap & Olympic Memories 24 Feb 2026

Today on The Player’s Box Jess is Miss Incredible, Madi was completely neglected by the entire podcast team, Des is still celebrating her birthday and Jenny had an unforced error in a car…again. Also, Jess’s recap on winning Dubai, tennis headlines, Olympic memories and 2026 storylines and more. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

27 | Iva Jovic in The Player’s Box 17 Feb 2026

Today we have a very special guest joining us in The Player’s Box — Iva Jovic! Jenny may be the new Quad God, Madi continues to be running’s biggest anti, Jess’s entire algorithm is Olympics drama, Des continues to be the reigning Gilmore Girls trivia champ and Iva’s singing almost got a disturbance call? Also, we get to know Iva, play some games and dive into all of the tennis headlines from the past week. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

26 | Hot Takes & Middle East Tournament Updates 10 Feb 2026

This week Des booked the same flight three times, Jess just wants a classic Marriott breakfast buffet and tensions rise as Jenny and Madi fight for their lives to describe girl pockets. Plus, updates on the Middle East tournaments, Des making the semis in Abu Dhabi and what’s next for everyone. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

25 | AO Recap, Tennis Calendar & Cheesy Apple Pie 03 Feb 2026

This week is the moment you’ve all been waiting for as Madi takes a bite of Jess’s cheese pie. Does she love it? Hate it? Does her face go through 17 different emotions while chewing? Watch and find out. Also, Jenny is back at it on the court and still bickering with Des off of it, Jess stole someone’s (middle?) seat on her flight and Des calls out her wooden spoon situation. Also, an AO round up, discussion of cameras at tournaments and what’s next. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

24 | Australian Open Headlines 27 Jan 2026

This week we have some wild reveals like Jenny and Jess’s ideal high fashion sponsors (Ralph Lauren and Reese’s?), Des learns she may have broken Madi’s one player’s box rule and Madi lets all of us know what she’s learned from the podcast….spoiler: lots of patience is required. They also give a recap of all of the Australian Open headlines up to this point! Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

23 | Australian Open 4th Round Preview - Madi vs. Jess 25 Jan 2026

We’re releasing a special pre-match minisode this week to acknowledge the first ever Player’s Box on court match. Madi and Jess up the stakes with cheese pie (a potential poisoning) and a Kelce jersey? Then, Jenny and Des choose their fighter, Madi or Jess, in a battle of absurd circumstances. Learn more about your ad choices. Visit megaphone.fm/adchoices

22 | Australian Open, One Point Slam & Tennis Headlines 20 Jan 2026

This week Madi gives us an update from her time in Australia including her McDonald’s order, Jess attended a musical down under, Jenny is Vegemite’s biggest fan and Des gives us the rundown on how you (controversially) play Rock Paper Scissors Plus, tons of tennis headlines and AO memories. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

21 | Brisbane Recap, United Cup & Australian Survivor 13 Jan 2026

We learn a lot in this episode of The Player’s Box. In summary: Des would die in humidity, Jenny would win Naked and Afraid, Madi just wants to drink a spritz on the patio and Jess would win Traitors, maybe while holding a lizard. Tune in to learn why, and also catch up on their time in Australia and all of the recent tennis headlines. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer. It is Executive Produced by Dani Klupenger, Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

20 | Coco Gauff in The Player’s Box 06 Jan 2026

Coco Gauff is our first-ever guest on The Player’s Box! Jess, Madi, Jenny and Des put their coolness to the test in a game of Coco or No-Go, they all play a game of Never Have I Ever, and Coco brings her very own Who Am I to the episode. They also, of course, chat about the 2025 tennis season. You can purchase Player’s Box merch here: linktr.ee/theplayersboxpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer and John Gurney. It is Executive Produced by Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

19 | Mini Episode - Fan Questions! 30 Dec 2025

We’re off this week for New Years, but wanted to give you some Player’s Box to hold you over. Jess, Madi, Jenny and Des answer your fan questions. We’re back with regular episodes next week with a very special guest - Coco Gauff! Learn more about your ad choices. Visit megaphone.fm/adchoices

18 | Mini Holiday Episode - Trivia! 23 Dec 2025

We’re off this week for the holidays, but we wanted to make sure you had a little Player’s Box to hold you over. Jenny and Jess face Madi and Des in a trivia showdown and their competitiveness comes out to play. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer and John Gurney. It is Executive Produced by Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

17 | Offseason Training, Holiday Gift Guides & Year End Awards 16 Dec 2025

This week Jess, Madi, Jenny and Des talk about their offseason training and schedules as they prepare for 2026. They vote on the first official Player’s Box Year End Awards, which cover this year’s tennis highlights. They also go through their holiday gift guides — which Player’s Box host would you want to be your Secret Santa? You can find links to their gift guides on the Player’s Box Amazon Storefront here: https://linktr.ee/theplayersboxpod Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer and John Gurney. It is Executive Produced by Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

16 | Group Chat Who Said It, Exhibitions & Missing Holidays 09 Dec 2025

This week Jess, Madi, Jenny and Des catch us up on their Thanksgivings, their time in Buffalo and what it’s like to miss holidays due to their schedules. Then, they play a game of Group Chat Who Said It where they have to guess who sent out of context texts from the Player’s Box group chat. Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer and John Gurney. It is Executive Produced by Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

15 | Thanksgiving Traditions, This or That & Buffalo 02 Dec 2025

This week we recorded before Thanksgiving so Jess, Madi, Jenny and Des discuss their plans, their favorite traditions and foods (who agrees with cheese on apple pie?). Then they discuss their upcoming trip to Buffalo before getting into this week’s Who Am I and fan questions. To learn more about A Lending Paw and donate, please visit: https://www.alendingpaw.com/donate Connect with the show and hosts on Instagram at: @MadisonKeys @JPegula @Jenny_Brady7 @Des_Krawczyk11 @ThePlayersBoxPod Submit fan questions to theplayersboxpod@gmail.com This podcast is edited by Marc Colcer and John Gurney. It is Executive Produced by Harris Lane, Rhapsody Voices and Rewired Talent. Learn more about your ad choices. Visit megaphone.fm/adchoices

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