The Player’s Box: Episode 15

Thanksgiving Traditions, This or That & Buffalo
Release Date: December 2, 2025
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

This episode of The Player’s Box is a festive, behind-the-scenes romp as the quartet of tennis pros—Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk—dive into their Thanksgiving traditions (or lack thereof), swap stories from the road, play games (including a Thanksgiving "This or That"), preview Jess’s Buffalo charity gala, and answer fan questions. Laughter, light roasting, and candid confessions abound as the hosts share personal mishaps, food hot-takes, and the realities of life on the tennis circuit.

Main Segments & Timestamps

1. Unforced Errors & Winners of the Week

01:09 – 06:21

Highlights:

• Jenny Brady narrowly avoids hitting a deer while driving, humorously acknowledging her consistent driving mishaps:

  “Apparently maybe I’m the problem because all of my unforced errors happen while I’m driving. RIP Iggy.” (01:44 – Jenny)

• Jess Pegula introduces her new puppy, Mabel—who promptly poops on the breakfast area’s banquet seating:

  "She jumps on everything. And so at some point, she jumped up there and decided to go number two." (02:36 – Jess)

• Maddie details 20 minutes of podcast technical difficulties, naming herself as the culprit:

  "There was lots of movement happening from one of us. I won’t single that person out…" (03:23 – Maddie)

• Desirae admits to burning cornbread stuffing at Friendsgiving ("oven on for six hours extra") but is pleased everyone had fun with Jeopardy and white elephant games.

Notable Moment:
The group tallies up Jenny’s driving-related errors with good-natured teasing, and Mabel the puppy makes her on-air debut.

2. Thanksgiving Talk: Plans, Traditions, & Food Debates

06:28 – 14:51

Whereabouts & Traditions:

• Desirae is in the desert after Friendsgiving; Jenny is headed to Boca/Raton and then Buffalo; Maddie to Pittsburgh and then Buffalo; Jess is already Buffalo-bound for the family and her charity gala.
• The quartet admits tennis tour life makes holiday traditions tricky—most years are spent away from home or at tournaments:

  "It's hard to have a consistent holiday tradition because we're very rarely, like, actually at home for holidays." (08:48 – Maddie)

Food Favorites & Controversies:

• Top Dishes: Mac & cheese, cornbread, various stuffings (“my mom’s stuffing is the best”—Jenny at 10:10).
• Hotly discussed: stuffing mix-ins (sausage vs. cranberries), sweet potato casseroles (with/without marshmallows), apple pie with melted cheese ("It's like sweet and salty!"—Jess, 12:47).
• Maddie proclaims herself “the anti-Thanksgiving person” regarding classic foods (11:54).
• Dessert must-haves: Pumpkin pie (Jenny), Apple pie (Maddie and Jess, who melts cheddar or American cheese on it), banter over the right cheeses ensues.

Memorable Quotes:

• "I think I'm, like, the anti Thanksgiving person, because all of, like, the foods that everyone is like, no, that's Thanksgiving, I'm like, no, thanks. I'll pass." (11:54 – Maddie)
• “My mom’s stuffing...phenomenal.” (10:10 – Jenny)

3. Hostess with the Mostest? Who Would Cook Thanksgiving

13:11 – 16:30

• Group agrees Des and Maddie are most trustworthy to cook (until Des confesses nearly burning cornbread).
• Maddie gets assigned main courses and desserts; Jenny offers to taste-test, Jess is dubbed “bartender” ("Espresso martinis all the way." – 15:23).

Notable banter:
“Could you imagine Dez, like, frying? There is no—well, I mean, yeah.” (14:21)

4. Thanksgiving ‘This or That’ Game

16:51 – 19:02

The hosts riff through quick-fire choices:

• Blankets or sweaters: Blankets (Des), Sweaters (Jenny)
• Pie: Apple (most), Pumpkin (Jess)
• Travel vs. Home: Hosting (Maddie, Des), Being hosted (Jess, Jenny)
• Football vs. Parade: Football unanimous
• Black Friday: Sleep in!
• Board games vs. movies: Board games.
• Family drama: “Lean into it. Drop little bombs all night to see who takes them.” (18:18 – Maddie)
• Kids or adult table: Split (kids – Jenny/Des; adults – Jess).
• Thanksgiving outfits/pets: All vote pets in outfits.

Hilarious quote:
“You just gotta be like…drop little bombs all night to, like, see who takes them.” (18:18 – Maddie)

5. The Ultimate Tennis Thanksgiving Table

22:17 – 24:56

If given five open seats, who would they invite?

• Jenny: Marat Safin (“he’s nice to look at” 22:33)
• Desirae: “Foe” (Frances Tiafoe) for boundless energy and likely being late
• Jess: Serena Williams (“she’d be down for a good time” 23:00)
• Maddie: Emma Navarro (“so weird and so funny”; “in the best way” 23:35), Laura Robson (karaoke machine, TikToks, and party hosting skills).

Memorable anecdote:
Maddie ships fancy napkins from the US to Laura Robson in the UK (“These are some expensive napkins…” 24:34).

6. Jess’s Buffalo Charity Gala Preview

25:03 – 27:32

• Jess explains the upcoming rescue/service dog benefit—her first major charity event, “Casino Royale” themed, complete with dressed-up dogs and non-profits.
• "We're like, kind of all panicking. It's also just a busy week with Thanksgiving, but it was kind of the only weekend that we could do it this year." (26:10 – Jess)
• The tennis crew, plus friends, are Buffalo-bound for the event and a “wing tour” and Sabres game.

7. Buffalo, Josh Allen, and the Great Wing Debate

27:32 – 32:36

• Jenny (a loyal Josh Allen fan) insists she’d be speechless if she ran into the Bills QB.
• The group plans a Buffalo “wing tour”; Jenny, ever the researcher, is critiqued for being too picky (“I just said that they look a little saucy, and I don’t love…” 31:12).
• Maddie ribs Jenny for overanalyzing wing joints based on “garnish.”
• “No, I just said that they look a little saucy, and I don’t love…” (31:12 – Jenny)
• The group plans to blog the adventure and see if Jenny keeps her word about being easy to please.

8. Davis Cup, Comebacks & Tennis Life

33:12 – 39:06

• Italy’s Davis Cup and Billie Jean King Cup three-peat lauded; hosts marvel at Italy's tennis fever.
• Story of young Kaboli idolizing Berrettini and winning Cup together is shared ("really cute" 34:17)
• Holger Rune back on court five weeks after Achilles surgery sparks discussion:
  • Dasha’s (Daria Kasatkina) social post about rehab exhaustion and progress is referenced.
  • Jenny: “It's so exhausting. It's so draining. You have to, like, do, like, those small progressions, and they are…It's more draining mentally than it is physically.” (37:14)
  • Maddie: Tennis comeback is “so much sitting in a chair swinging a racket you want to break all of your rackets.” (36:51)

9. Autographs & Boundaries: The Connor Bedard Debate

40:25 – 47:00

• Hockey’s Connor Bedard goes viral for refusing an autograph from an adult reseller; hosts reflect on similar experiences.
• Maddie: “I'll just be like, are you selling these? ... Since it’s my face, I kind of want to get paid for it.”
• Desirae: “The best part is when you…they come back, it’s printed, and they're like, can you sign it? And I’m like, whoa.” (42:32)
• Jess: “From a female perspective…the boundaries thing gets really weird because they tend to always be older men. It’s just a little creepy…When that happens, it kind of ruins your want to do it again.” (45:18)

10. Pop Culture Round-up

47:19 – 53:38

• Maddie touts Real Housewives of Salt Lake City as “absolute cinema” and recaps the drama (“it is so funny—all of the comments are so unhinged” 48:59).
• Jenny quickly worn out after one wild episode of RHOSLC, mentions a castmate arrested for defrauding the elderly (“it all unfolded on camera” 50:52).
• The group discusses Secret Lives of Mormon Wives, Dancing with the Stars finale predictions, and “Landman” as the next show on the queue.

11. Who Am I? – Guess the Player Game

53:38 – 55:32

• Desirae delivers clues about a current British player whose home turf is Wimbledon, and whose game is marked by grit (listener challenge to guess in the comments).
• Previous answer: Anna Blinkova (revealed by Jess).

12. Fan Questions

55:32 – 61:03

Q1: Pros/cons of playing doubles with a close friend?

• Des: "Can be great…Playing at a high level with your best friend is special. But, it can be hard if a match goes south—how do you navigate that?" (56:21)
• Jenny: “Don’t mix business with…pleasure.” (57:48)

Q2: Favorite match lost but played well?

• Jess: “A lot of my recent matches with [Aryna] Sabalenka…You lose but…you feel like you put your best self out there.” (58:52)
• Maddie: Wimbledon vs. Jasmine Paolini—“unbelievable atmosphere…super fun, but…walked off in tears.” (59:38)
• Jenny: US Open 2020 vs. Naomi Osaka—“probably one of the best matches” (59:59)
• Des: Recalls several high-level matches; “can’t just go off the court and be so pissed…done such good things in the match.” (60:35)

Notable Quotes & Moments

• “Lean into it [family drama]. Drop little bombs all night to see who takes them.” (18:18 – Maddie)
• “If you do sell them, I feel like since it’s my face, I kind of want to get paid for it.” (41:44 – Maddie)
• “I think you just need to communicate…anything.” (58:33 – Desirae, on doubles with friends)
• “It’s more draining mentally than it is physically.” (37:14 – Jenny, discussing sports rehab)

Episode Tone

Conversational, candid, and filled with sisterly ribbing. The hosts alternate between nostalgic, tongue-in-cheek, and laugh-out-loud funny, giving fans a window not just into their lives as athletes, but as friends juggling wild travel, sweet and chaotic dogs, and the quirks of tennis tour life.

For Listeners

Whether you're in it for the tennis, the holiday banter, or just to hear athletes be utterly themselves, this Thanksgiving episode is a warm, relatable, and thoroughly entertaining listen.

Next Time: Tune in for more tales from the tennis road, unfiltered opinions, and fan Q&A (and to hear if you guessed Des's mystery Wimbledon Brit right).

[End of Summary]