The Player's Box
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.
Episodes
43 | Roland Garros Week Two & More Headlines
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.
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42 | Roland Garros Week One & Rank and Reveal
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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41 | Live from Paris: Roland Garros & Travel Days
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 r
40 | Tennis Updates & Top 5 Horror Movies
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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39 | Italy, Iconic Movies & Met Gala
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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38 | Rome, Pet Peeves & Low Stakes Advice
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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37 | Madrid Open, Spring Cleaning & Hallelujah
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_Br
36 | Tennis Headlines, Horoscopes & Europe
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!
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35 | Charleston Champions Corner, The Hot Seat & Europe
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
34 | Charleston Open, Clay Season & Reality TV
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_Br
33 | Alex Eala in The Player’s Box
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 kno
32 | Miami Open Week One
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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31 | Miami Open Memories & Indian Wells Headlines
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
@Jenn
30 | Indian Wells Update, Combined 1000s & Sam Querrey Joins
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.
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29 | Indian Wells Memories, Headlines & More
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 ques
28 | Dubai Recap & Olympic Memories
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_Krawcz
27 | Iva Jovic in The Player’s Box
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
26 | Hot Takes & Middle East Tournament Updates
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_Krawcz
25 | AO Recap, Tennis Calendar & Cheesy Apple Pie
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 roun
24 | Australian Open Headlines
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!
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23 | Australian Open 4th Round Preview - Madi vs. Jess
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.
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22 | Australian Open, One Point Slam & Tennis Headlines
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
21 | Brisbane Recap, United Cup & Australian Survivor
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:
@MadisonK
20 | Coco Gauff in The Player’s Box
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.
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19 | Mini Episode - Fan Questions!
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!
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18 | Mini Holiday Episode - Trivia!
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 po
17 | Offseason Training, Holiday Gift Guides & Year End Awards
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 Sto
16 | Group Chat Who Said It, Exhibitions & Missing Holidays
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
15 | Thanksgiving Traditions, This or That & Buffalo
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.
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14 | Tennis Headlines, Most Likely To & Who Am I
This week Jess, Madi, Jenny and Des cover all of the major tennis headlines of the week. They then play a rapid fire game of most likely to - tennis edition. We end with a new game of Who Am I where they use 3 clues to describe another player.
Connect with the show and hosts on Instagram at:
@MadisonKeys
@JPegula
@Jenny_Brady7
@Des_Krawczyk11
@ThePlayersBoxPod
Submit fan questions to the
13 | What Would You Do & Winners of the Week
This week Jess, Madi, Jenny and Des play a big game of what would you do — tennis edition. They also dive into why there tends to be coaching changes at the end of the year, and how that process works. They end, of course, with fan questions.
Connect with the show and hosts on Instagram at:
@MadisonKeys
@JPegula
@Jenny_Brady7
@Des_Krawczyk11
@ThePlayersBoxPod
Submit fan questions to thep
12 | Riyadh Wrap Up & End of Season Reflections
This week Madi, Jess, Jenny and Des come together for a big end of year wrap up. First they discuss the WTA Finals and Jess and Madi chat about their time in Riyadh. Then, they chat about the ATP Finals before taking a look back on their seasons as a whole.
Connect with the show and hosts on Instagram at:
@MadisonKeys
@JPegula
@Jenny_Brady7
@Des_Krawczyk11
@ThePlayersBoxPod
Submit fan qu
11 | Riyadh, Egg Freezing & Embarrassing Moments
This week, Jess and Madi come to us from Riyadh and give us an update on all of the pre-event details including the behind-the-scenes of their photoshoot. Then, Des gives us an update on her recent egg freezing journey and we hear Jenny’s most embarrassing locker room moment.
Connect with the show and hosts on Instagram at:
@MadisonKeys
@JPegula
@Jenny_Brady7
@Des_Krawczyk11
@ThePlayersBo
10 | Halloween Stories, Social Media & Confessions
This week, Jess, Jenny, Madi and Des dive into Halloween stories and what they like (and don’t like) about this season. Then, they chat about recent gambling news that broke in the NBA, leading them to some of the comments they have to constantly deal with on social media. We end with some on court confessions and fan questions.
Connect with the show and hosts on Instagram at:
@MadisonKeys
@
9 | Six Kings Slam, Fitness Trends & Confessions
This week everyone is back together as Des updates us on how things are going in Japan. They talk about their thoughts on the Six Kings Slam before jumping into fitness trends, training and confessions.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk11
ThePlayer
8 | Staying Motivated & Speaking Gen Z
Jess, Jenny and Madi are without Des this week due to navigating four different timezones. They dive into how to stay motivated towards the end of the year, anti-doping testing stories and more. Then, they take their swing at Gen Z slang.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk1
7 | WTA Finals, Fan Gifts & Recording Internationally
Join Jess and Des in China and Madi and Jenny in the States as they battle WiFi, lags and recording across the globe from each other. They cover recent tennis news, the WTA Finals, meeting fans at the China Open and more.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk11
ThePlay
6 | Friendship Origin Stories, Socializing on Tour & China Update
Jenny and Madi are on their own this week because Jess and Des couldn’t connect from Beijing. We learn more about where their friendship started and how it’s changed and developed over the years. Then we go into fan questions and end on a Jess and Des update from China!
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
5 | Unforced Errors, Billie Jean King Cup and Travel Disasters
On this week’s episode Jess, Madi, Jenny and Des kick things off with a new segment of Unforced Errors where they discuss what went wrong during their weeks. Then they go into the Billie Jean King Cup and details about their upcoming trips to China.
Giveaway announcement! Be sure to follow @theplayersboxpod on Instagram and then subscribe on The Player’s Box YouTube page and leave a comment on
4 | Dating on the Tour, Travel Pet Peeves & Best Slam
Join Madi, Jess, Des and Jenny this week as they discuss the challenges of dating on the tour, all of their travel pet peeves as they prepare to head to China and then answer some great fan questions about each other’s best shots and the best grand slam.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk11
Th
3 | US Open Wrap Up, Breaks During a Match and What’s Next
Join Jess, Madi, Jenny and Des as they do their final recap of their time at the US Open — including their peaks and pits, watching the semi-finals and all of the influencers and celebrities spotted at the tournament.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk11
ThePlayersBoxPod
Submit fan questions to theplayersb
2 | US Open Match Updates, Most Likely To and Choosing Balls
On this week’s episode of The Player’s Box, Jess, Madi, Des and Jenny recap their time so far at the US Open. Then, you get to know The Player’s Box with a round of most likely to questions. They also encounter the most wild fan question and answer session yet.
Connect with the show and hosts on Instagram at:
MadisonKeys
JPegula
Jenny_Brady7
Des_Krawczyk11
TheP
1 | US Open Highlights, Celeb Encounters and Tough Moments
On the premiere episode of The Player’s Box, hosts Madison Keys, Jessica Pegula, Jennifer Brady and Desirae Krawczyk break down everything you should know heading into the US Open. They talk scheduling, kits and some of the toughest moments from past years.
This episode is sponsored by Dragos Capital - we acquire businesses and real estate from owners ready for their next chapter. Connect with
Bonus - Why We Started The Player’s Box
Madi, Jess, Jenny and Des take you from the group chat to the creation of the podcast — what made them finally launch one after years of talking about it? Plus, fan questions!
This episode is sponsored by Dragos Capital - we acquire businesses and real estate from owners ready for their next chapter. Connect with us at DragosCapital.com
Connect with the show and hosts on Instagram at:
M
The Player's Box Trailer
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, Jenny 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 cultu
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