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

Summary

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

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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.

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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!

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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)

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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

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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.

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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)

Transcript

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[Madison Keys]

This is the players Box.

[Desiree Krafczyk]

Hi everyone. Welcome back to another episode of the Players Box. I'm Desiree Krafczyk alongside Jenny Brady, Madison Keys and Jess Fagula. A friendly reminder to please give our podcast five stars and subscribe on YouTube. So, so we are doing a special mini episode today because we've got a huge fourth round battle between our very own co hosts Jess and Maddie. And yes, it's the first ever podcast co host matchup.

[Jenny Brady]

Maddie, your next match, fourth round is against fellow American Jessica Bagula. What do you think about the matchup?

[Madison Keys]

It's a tough matchup. We've only played, we've played I think three times on the tour now in the last couple of years and it's gone both ways. We played each other last year in the Adelaide final and it was actually a really good match. I've always been really impressed with just how like, just how steady Jess is. It's like, you know that she's always gonna like, make the best decisions and she's got that sneaky drop shot that you always have to be looking out for. But it was funny because it was like two years ago when I was, I was like winning a few matches in a row and I was like making quarters, made like quarters of three tournaments in a row and Bjorn was like, how do you feel? I was like, I'm in my Pegula era. I just quarter every week all of a sudden. So it's just always like, Jess is just always like winning. She's always there. She's just everywhere.

[Jenny Brady]

Yeah. Okay, Jess, you play Madison Keys, next up in your fourth round match. What do you think about the matchup?

[Jess Fagula]

Yeah, so when we played in Adelaide last year, I thought, you know, it was a really good match. It went to three sets and I think Maddie was playing some stellar tennis so much that, you know, 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 a really hard draw and we thought she was going to win Australian Open and she did. So I guess that was a good call by us. But, you know, definitely going to be tough for me tomorrow knowing that she plays so well down here.

[Madison Keys]

Jess is like, I hope I don't see that level.

[Jess Fagula]

Yeah. I'm like, it's great. But, like, tomorrow, like, she can not play that level. It'll be great.

[Jenny Brady]

Don't jinx it for me.

[Madison Keys]

Don't jinx it.

[Jenny Brady]

Don't play stellar. I don't know what to say. She hopes. Jess hopes Maddie doesn't play stellar tomorrow.

[Jess Fagula]

I hope it's.

[Desiree Krafczyk]

And Maddie vice versa. Not the drop shots.

[Jenny Brady]

Not my first choice of words.

[Jess Fagula]

I have to watch out for the forehand hack. Can't wait to see that tomorrow.

[Madison Keys]

I watched your match, your last match. I was scouting, and I was watching your highlights, and you missed a hack slice forehand, and you were so annoyed, and I was like, heh, heh, heh.

[Jenny Brady]

She's gonna hit you up for some lessons.

[Jess Fagula]

I can't wait. I seriously, I've been working on it, so I hope I can hit a good one tomorrow. And if I win the point, I'm gonna be like, yes, take that.

[Madison Keys]

If I get you on any of them, I might just, like, immediately start laughing.

[Jess Fagula]

No, I.

[Madison Keys]

Seriously, that's what I want to see.

[Jess Fagula]

I think so, too. I think I'm gonna start laughing, take. Depending on the score, or I'm going to take the ball and be like, this effing slice forehand. We'll see.

[Desiree Krafczyk]

So, Jess, when did you first meet Maddie?

[Jess Fagula]

I honestly have no idea. I feel like we. It was definitely very young. We were probably. I'm, what, a year older? So maybe you were like, 12 or 13, and I was maybe 14, something like that. I want to say, I remember we talked. Remember I told you about when we played Ponte Vedra? I feel like that was probably the first because we were very young. I think that was probably the first time. I don't even know if we spoke, but that I had ever, like, probably been around you, because I wasn't at Everett or anything when you were there. Does that sound, like, accurate?

[Madison Keys]

Yeah, I think that was the first. That was definitely the first WTA event that we were both at. It was both of our first. I think so. So I remember. I remember being around and everyone being like, oh, it's also Jess's first WTA event, and I think we had kind of crossed paths in junior. Like, some junior stuff, but not a whole lot.

[Jess Fagula]

We did. Cause I didn't really play that much, and you didn't like, I Played Southern, so I played like a lot of. More like smaller, like southern sectional things. And I feel like you did it.

[Madison Keys]

I played Florida.

[Jess Fagula]

Yeah. So I think that's why we didn't really cross paths that much. And then at nationals, I remember playing Sloan and like those girls, but never. I don't think you were playing or. I don't know.

[Madison Keys]

I feel like the first. The first, like, match that I really remember us playing was the Indian Wells. Pretty pre quali.

[Jess Fagula]

Yes.

[Madison Keys]

And we played in the finals and I was so salty because I won. And then we both. But we both ended up getting the wild cards and I got the number one seed in Quali. You got in my mind a way better draw than you qualified.

[Jess Fagula]

I qualified, Yes. I qualified. And that was like the first big tournament that I ever qualified at. And then I remember you lost to Paolo or Machea, like first or.

[Jenny Brady]

Oh, my gosh.

[Jess Fagula]

You did.

[Madison Keys]

No, it wasn't for that. I don't think it was Ormachea, but it was all. I remember I played Paula. You played Paula, I think.

[Jess Fagula]

Who did you play?

[Madison Keys]

I played.

[Jess Fagula]

I do remember that.

[Madison Keys]

The number one seed. And I was like, this is. I won. Just got the better draw.

[Jess Fagula]

And then, yeah, we ended up both getting wild cards for making the finals of the pre qualifying event at Indian Wells, which is literally a pre qualifying to get a wild card into the qualifying. And we like killed everybody in the draw and it was just like us in the finals and yeah, that was like the first time we probably played. And the first time I really like. Yeah, core memory, I think.

[Desiree Krafczyk]

But it was never like, oh, my God, Maddie. Oh, like, oh, my God, Jess. You know, like, you know when you first, like, meet someone, you're like, I.

[Jess Fagula]

Think I don't like, Maddie was like, become really good friends after Maddie. I've never felt like that Maddie was like, up here and I was like, down here. That's how I felt. Because Maddie was always like this, like from like when we played Pon of Edra. Like, I always did well. And then Maddie was always like, she was beating like some girl top 100. And it was like the youngest ever tour win, like, ever. Because you were like 2:12 or something. I don't even know. And I was always a year older. So I feel like Maddie was like touted so much. So 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. It was like maybe three sets.

[Madison Keys]

But you, like, killed me in the third yeah.

[Jess Fagula]

Yeah. I think it was, like, 6:1 or 6:0 in the third, but I won the second. And then I think I realized, like, oh, my gosh, like, I. To meet Madison Keys. And then I, like, you didn't win another game. No, I think she got ahead of herself.

[Desiree Krafczyk]

Yeah. The match isn't funny, because in the moment, Jessica.

[Jess Fagula]

Yeah. I just, like, I never. I don't know, we had completely different junior lives, so I just, like. Yeah, Maddie was always like, oh, my gosh, Madison Keys. Like, she's supposed to be, like, the next big thing. And that was always when I was coming up. That's like, always. I don't know what was in my head. Thoughts.

[Jenny Brady]

Maddie has no comment.

[Jess Fagula]

Maddie's just not wrong. Right.

[Madison Keys]

I mean, thanks. Well, it was also, like, I played. I played a ton of pro events super young, and once I started playing, like, the challengers and stuff, like, I kind of moved up the rankings fairly quickly, and. 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, and it would be like, I would always kind of be like. Like, I wonder where Jesse is. And then, like, I'd see your name again, and you would do well, and then you'd kind of be gone. And then I vividly. Sorry. I vividly remember you winning D.C. and you being like, this is the first time I've ever won a tournament. And I was like, ever. Like, she's so good. What do you mean? And then from there, it was like, now you're.

[Jess Fagula]

Yeah, then I was fine, so. But, yeah, now I'm Jess. No, that was true, because I was like, I feel like you did really well, really quickly. And then I started to do well, but I kept getting hurt. So, like, we were actually, like, I don't think that far at one point in the rankings, kind of. I don't know at what point this was. And I was like, I feel like I. But I wasn't like, a USTA or, like a touted kind of, like, junior, but I was actually doing pretty well. And then I got hurt, and then I would come back and I get back to, like, 150. And then I kind of get hurt, and then I come back and I get back in the top 150. And that happened, like, two or three times until finally, like, I got healthy, and then I. That's when I, like, finally cracked to the top 100, and then I won DC. So it was like, kind of A weird in and out kind of situation.

[Madison Keys]

Yeah, like I said, we're just.

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[Desiree Krafczyk]

Let's get into the trash talking, girls. Okay, none of this stuff of this. Okay. We have a couple things that were going on. We've heard a Maddie, if Maddie loses, she's got to eat Jess's favorite thing. Eat cheese on apple pie. Or we've got, if Jess loses, she's got to wear the chief jersey. You know, what's the thoughts on that? What's like, which is worse?

[Madison Keys]

I mean, it's clearly mine.

[Jess Fagula]

Are you kidding me?

[Jenny Brady]

Chief Jersey 100 is worse.

[Madison Keys]

Cheese on apple pie is pretty brutal.

[Jess Fagula]

My family owns the Buffalo Bills. They've owned it. I have to sit there and wear this. And then there's gonna be pictures and then people are gonna be like, true. Jess clearly lost a bet and I'm gonna have to suffer. Mine's definitely.

[Madison Keys]

When you came after me for the apple pie, I was like, what's the worst thing that I could possibly think of for Jess? For retaliation.

[Jess Fagula]

We were walking the press and we saw each other and I was laughing about how they're talking about this. You know, first ever podcast, podcast host playing each other historical moment. And my agent was like, you guys need to come up with like a funny bet or something. Something. And then I literally like yelled down the hallway, I was like, apple pie.

[Madison Keys]

With cheese on it. She's like, no, never.

[Jess Fagula]

And I'm like, nope, I'm sticking to it. Yeah, she refuses. But then she came up with that one. So I don't know. We'll see.

[Desiree Krafczyk]

Would you rather wear, like, Chief. Would you rather wear the Chief jersey or, like, a Taylor Swift?

[Jenny Brady]

She keeps saying Chief.

[Desiree Krafczyk]

Sorry, I don't know. Would you rather wear a Chief's jersey or a Taylor Swift shirt?

[Jess Fagula]

I guess. Oh, God, that's really hard.

[Desiree Krafczyk]

I mean, I could lend you the Taylor Swift shirt. I have that. So, I mean.

[Jess Fagula]

I think I'd maybe rather wear a Swift. Taylor Swift shirt.

[Desiree Krafczyk]

Oh, you heard it here first.

[Madison Keys]

I wanted to kind of double down, and I wanted the Chief's jersey with, like, a whole stack of, like, the Taylor Swift French bracelets. I felt like that felt better since. I don't know, I just. I still kind of stand by. I think the pie is pretty gross, so I was like. I feel like the combo of the jersey and the friendship bracelets is.

[Jess Fagula]

What's the name on the back? Swift. Like Kelsey Swift. Like a hyphen.

[Madison Keys]

Who's the. Or. Or like, maybe. I don't know if I want, like, Travis Kelce or if I want Patrick Mahomes. Oh, my God.

[Jenny Brady]

My homes would be rare.

[Jess Fagula]

Well, you can make a decision.

[Jenny Brady]

I don't know.

[Desiree Krafczyk]

For every friendship bracelet, we will have to see what happens with that. So stay tuned, everyone, to see what happens.

[Jenny Brady]

Okay, since we are cheering you both on, we can pick a winner for other showdowns. Who would be better at Real Housewives? Maddie.

[Jess Fagula]

Maddie. For sure.

[Madison Keys]

I would be so good at Housewives.

[Desiree Krafczyk]

You're not supposed to pick, though.

[Jenny Brady]

You're not supposed to pick.

[Desiree Krafczyk]

We are the ones that guess.

[Jenny Brady]

It's me and Des. Okay.

[Desiree Krafczyk]

Okay. This is our game.

[Jenny Brady]

Yeah, this is our game. This is our time to shine. Since you guys are shining tomorrow.

[Madison Keys]

Okay, gosh. Give us our 10 minutes.

[Jenny Brady]

Let's give a little bit of a spotlight. Okay. Who would be better at Real Housewives? Oh, what? Okay, wait.

[Jess Fagula]

Okay.

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Oh, my God.

[Jenny Brady]

Crying convincingly. Desiree, lock in.

[Desiree Krafczyk]

Crying.

[Jenny Brady]

Crying convincingly on camera. Maddie.

[Desiree Krafczyk]

I. Yeah, I was gonna say Jess, because, like, she doesn't really cry and, I don't know, she's calm, cool, and collected. So.

[Jenny Brady]

Yeah, that's why she wouldn't be good on camera.

[Desiree Krafczyk]

Oh, okay.

[Jenny Brady]

Picky. Oh, becoming a fan favorite. Can we say both?

[Jess Fagula]

I was gonna say I feel like we're both fan favorites.

[Jenny Brady]

Yeah, they're both pretty favorited by the fans. Winning shop till you drop. I'm going to have to say Maddie.

[Desiree Krafczyk]

Maddie.

[Jenny Brady]

Taking their way into.

[Desiree Krafczyk]

Wait, what?

[Jenny Brady]

Sorry, sorry. Talking their way into a free upgrade.

[Desiree Krafczyk]

Jess H. Oh, okay.

[Jess Fagula]

Really? I would say.

[Desiree Krafczyk]

Yeah, I was going to say, Maddie, I would never.

[Madison Keys]

No, I'm the person that's like, oh, my order is wrong. That's okay, I'll eat it. That's true.

[Jenny Brady]

Yeah.

[Jess Fagula]

But I feel like. Well, whatever. I'm not gonna go. It's.

[Desiree Krafczyk]

Jess, this is our game. Okay?

[Jenny Brady]

Yeah, Jess, I need you to pipe down.

[Madison Keys]

Stop trying to kill yourself, please.

[Jenny Brady]

Losing their receipt immediately.

[Desiree Krafczyk]

Jess, I've.

[Jenny Brady]

Yeah, Jess. Impulse buying. Something wildly unnecessary, naughty.

[Desiree Krafczyk]

She unnecessarily bought you this stand for your phone, which was okay.

[Madison Keys]

Yeah, Maddie, that was pretty necessary.

[Jess Fagula]

Yeah.

[Madison Keys]

Also, it's a business expense.

[Desiree Krafczyk]

Yeah, It's a write off.

[Jenny Brady]

It's a write off. Talking their way out of a speeding ticket. Jess. Because she's done it before.

[Desiree Krafczyk]

I think. I think Maddie would crack.

[Madison Keys]

Oh, I don't think I would crack on that one.

[Jess Fagula]

No.

[Jenny Brady]

Burying a dead body. Ooh, Maddie. I was gonna say Maddie. I don't know if that's because she's ride or die.

[Jess Fagula]

Yeah, she's watched all the.

[Desiree Krafczyk]

She's got the shovel and she's like.

[Jenny Brady]

She'S ride or die.

[Desiree Krafczyk]

She's ready.

[Madison Keys]

I have watched all the shows too.

[Jenny Brady]

Keeping a straight face in a serious situation. Maddie.

[Desiree Krafczyk]

Yeah, Maddie.

[Madison Keys]

Yeah.

[Jenny Brady]

Jess would laugh. Everybody not panicking in a crisis. Jess, Jess, Jess. Handling a full on adult meltdown calmly.

[Jess Fagula]

Jess.

[Desiree Krafczyk]

Jess.

[Madison Keys]

Sorry, Maddie.

[Jenny Brady]

Calling customer service and actually winning.

[Desiree Krafczyk]

Oh, Jess.

[Madison Keys]

I'm gonna say actually, I don't know.

[Jenny Brady]

Yeah, I don't know. I was gonna say Jess, but she struggled with her one customer service issue, so I'm gonna have to go with Maddie.

[Desiree Krafczyk]

Okay, I'll let you thoughts ride that one.

[Jenny Brady]

I don't know.

[Desiree Krafczyk]

I feel like Maddie can get sassy and like she'll be, you know. Yeah, she'll just give her point and.

[Jenny Brady]

Yeah, yeah, she'll win. Assembling IKEA furniture without crying.

[Desiree Krafczyk]

Maddie, I think Maddie.

[Jenny Brady]

Yeah, Maddie.

[Desiree Krafczyk]

She's like into the furniture.

[Jenny Brady]

I don't think Jess would cry.

[Desiree Krafczyk]

I feel like she'd get overwhelmed.

[Jenny Brady]

Yeah.

[Desiree Krafczyk]

I love what we're talking about them as. They're just sitting here, you know, like.

[Madison Keys]

We were told we're not allowed to speak.

[Jess Fagula]

Yeah, you're not. You're right.

[Jenny Brady]

This is our game.

[Jess Fagula]

So you.

[Desiree Krafczyk]

That was a fun game. I liked it.

[Jess Fagula]

Yeah.

[Desiree Krafczyk]

It was just Jenny and I. Yeah.

[Jess Fagula]

Should we just run through and do.

[Madison Keys]

Jenny versus DEZ real quick?

[Jenny Brady]

Oh.

[Madison Keys]

Oh, God, I feel targeted.

[Jenny Brady]

It's not. It's not about us.

[Madison Keys]

We're done with us.

[Jess Fagula]

Yeah.

[Jenny Brady]

Okay. Well, good luck to you both. Please leave us a rating and review. It helps people. Find out about the podcast. And don't forget to watch us on the players box YouTube page and send us fan questions on Instagram or to our email. May the odds be ever in your favor.

[Madison Keys]

Turn the whistle.

[Desiree Krafczyk]

Yeah.

[Jess Fagula]

Wow. That was an unhinged episode.

[Desiree Krafczyk]

It was a great episode.