The Player's Box

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. 

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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. 

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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. 

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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.

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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. 

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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 [email protected]

This podcast is edited by Marc Colcer. It is Executive Produced by D...

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. 

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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. 

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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 re...

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. 

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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/onemedic...

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

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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 medi...

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/healt...

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

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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

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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.  

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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, mone...

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. 

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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. 

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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:

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On...

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. 

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Connect with the show and hosts on Instagram at:

@MadisonKeys

@JPegula

@Jenny_Brady7

@Des_Krawczyk11

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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 th...

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! 

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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. 

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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. 

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Connect with the show and hosts on Instagram at:

@MadisonKeys

@JPegula

@Jenny_Brady7

@Des_Krawczyk11

@ThePla...

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 [email protected]

This podc...

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 que...

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. 

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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 [email protected]

Thi...

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_Bra...

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. 

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Connect with the show and hosts on Instagram at:

@MadisonKeys

@JPegula

@Jenny_Brady7

@Des_Krawcz...

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@gmai...

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 questi...

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 [email protected]

This podcast is edited by Marc Colc...

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 [email protected]

This podcast is edited by Marc Colcer. It is Exec...

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...

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 [email protected]

This podcast is edited by Marc Colc...

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. 

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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

@ThePlayersBoxP...