The Player's Box
Episode 12 | Riyadh Wrap Up & End of Season Reflections
Release Date: November 11, 2025
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk
Episode Overview
Theme:
This episode is a year-end reflection and a behind-the-scenes recap of the WTA Finals in Riyadh. The hosts share personal mishaps, discuss the much-talked-about Finals photoshoot, reflect on their best ("wow") moments and challenges of the tennis season, spotlight notable tour storylines, and end with candid fan Q&A covering both tennis and pop culture.
Key Discussion Points & Insights
1. Unforced Errors of the Week (00:27-04:13)
- Madison: Flew halfway across the world for Year End Finals, got sick, and had to withdraw.
- Jess: Shower flooded on the first day at finals.
- Jenny: Accidentally honked her car horn with her chest/elbow, got flipped off by another driver.
- Desirae: At a wedding, botched the mix on fertility injections, had to call nurse and doctor, missed dinner speeches but made it back for dessert.
Notable Moment:
"My unforced error is flying halfway across the world and then getting sick as matches start at year end finals and then having to pull out..." — Madison Keys (00:40)
Funniest Incident:
"I just needed to readjust my seats...my chest hit my steering wheel and it went...' — Jenny Brady (01:32)
2. The WTA Finals Photoshoot in Riyadh (06:01-11:50)
- Comparison with previous years (dresses, stylists, more options, but hectic).
- Cultural dress code limited photo locations and outfit choices.
- Critique of group photo posing ("doubles girls behind the others"), no smiling photos.
- Madison's creative idea: future finals shots in gowns, barefoot in the desert.
Quotes:
"It was a very different experience compared to Singapore...but this time, at least, we all looked like we were going to the same event for the first time." — Madison Keys (06:29)
"We all should have been in...beautiful gowns and everything, but, like, barefoot in the desert, like, walking through the sand, right?" — Madison Keys (10:50)
3. Riyadh: Event Atmosphere & Reflections on Change (12:12-13:35)
- Despite illness spreading among players, the event logistics and fan atmosphere improved significantly compared to previous years.
- More engaged, knowledgeable fans, and sections cheering for specific players.
Memorable Note:
"There was literally, like, at one point, like, I walked into the training room and I was like, I hear there's people that are sick. And they're like, who isn't sick?" — Jess Pegula (12:22)
On Fans:
"I thought they were great...because last year I felt like they didn't know how to cheer...this year, it felt like way more chance...cheering, sections of different types of fans..." — Jess Pegula (13:33)
4. End of Season Reflections & "Wow" Moments (14:22–23:51)
- Madison: Won her first Grand Slam at Australian Open (AO); career-high ranking (#5), most wins in a season, made WTA Finals.
- Desirae: Tough year managing new partnerships and pressure; highlights semi at Wimbledon, learning and growing.
- Jess: "Wow" mental stretch in Asian swing—grinding through multiple tough wins, clinching Year End Finals qualification.
- Jenny: Comeback from significant surgery; from crutches to full training, started hitting again at US Open.
Quotes:
"I came home with Daphne, which was like super fun...most matches I've ever won in a season...I was five in the world and then Jess overtook me again." — Madison Keys (17:23)
"It was more managing and seeing, taking one tournament in one match at a time and with the switching of partnerships, that was really tough." — Desirae Krawczyk (18:32)
- Discussion on the athlete mindset: tough self-critics, hard to celebrate successes, always pushing for more.
"I feel like it's partially like, what makes, I'd say us in athletes really good is that we're always, like, trying for more, and it's like, we always want to improve..." — Madison Keys (23:10)
5. Matches & Moments They’d Replay (25:15-27:07)
- Desirae would relive her off-court week in Italy ("not going for negativity here!").
- Madison would relive Australian Open—the journey through tough three-set matches and “turning point” in Adelaide.
- Group laughs at the “hyping up”/“jinxing” dynamic: Jenny’s encouraging texts jinxing Jess at Wimbledon.
Humorous Highlight:
"Jenny, don't ever effing say that I'm gonna win Wimbledon ever again." — Jess Pegula (31:28, referencing group chat superstition)
6. Favorite 2025 Tour Storylines (32:04-36:04)
- Standouts: Rybakina’s winning streak, Boco winning Montreal as a teenager wild card, Vacherot’s Shanghai run as an alternate, Amanda Anisimova’s return/semi/finals at key events after mental health break.
- Other highlights: Belinda Bencic’s resurgence to Top 10 after motherhood, ATP race drama, differences in ATP/WTA Finals qualification timing.
Quotes:
"I think that Amanda was a very fun storyline to follow. Really cool to see...she took some time off, prioritized her mental health...and is now, you know, back." — Madison Keys (33:45, 34:20)
7. Pop Culture & Other Sports Check-in (41:00–44:55)
- LA Dodgers win World Series—Des watched her first full baseball postseason, even at a wedding.
- "Bucket list" moment: Watching baseball while at a wedding.
- Buffalo Bills beat the Chiefs again in regular season—discuss “jinxing,” banter about sports superstitions.
- Brief on Tom Brady "cloning" his dog (group’s confusion and amusement).
Notable Quotes:
"I've never watched so much baseball ever." — Desirae Krawczyk (41:32)
"So Drake May is the Patriots quarterback...now there are these memes that they think Tom Brady, like, cloned himself and he came back as Drake May..." — Jess Pegula (44:29)
8. Fan Q&A (46:28–58:13)
Ceremonial Mishaps
- Jenny’s 2021 AO final speech with Naomi Osaka: “Jenny or Jennifer?” meme explained.
"And she said, 'Do you like to be called Jenny or Jennifer?' and I go, 'Jenny.' ... And then she goes, 'I would like to congratulate Jennifer.'" — Jenny Brady (47:04-47:42)
- Group consensus: This meme moment can't be topped.
Sleep While on Tour
- All three use the same travel pillow, recommended by Madison (“Coop” brand).
- Madison will campaign for firmer mattresses; has slept on floor/bench to avoid back pain.
"I'll actually call down and be like, do you guys have a firmer mattress anywhere?" — Madison Keys (51:41)
- Discussion of pillow sizes, vacuum-sealing for travel, and Europe’s “challenging” bedding.
Translator for Shohei Ohtani (LA Dodgers)
- Debate if Shohei “needs” a translator (after the interpreter gambling scandal).
- Jess: “I’ve heard that he has so many fans in Japan that people like to hear him talking in Japanese, which is fine. But I feel like he should do both more.” (57:37)
- Madison: “If someone who can speak another language wants a translator, like, go for it, bro.” (57:57)
Notable Quotes & Fun Banter
- “We all should have been in beautiful gowns and everything, but, like, barefoot in the desert, like, walking through the sand, right?” — Madison Keys (10:50)
- “It's easy to be your own critic.” — Jenny Brady (23:21)
- “If someone who can speak another language wants a translator, like, go for it, bro.” — Madison Keys (57:57)
Timestamps for Key Segments
- Unforced Errors: 00:27–04:13
- WTA Finals Photo Discussion: 06:01–11:50
- Event & Fan Atmosphere: 12:12–13:35
- Season Reflections & Mindset: 14:22–23:51
- Replay Matches & “Jinxing” Stories: 25:15–31:41
- Favorite Storylines: 32:04–36:04
- Pop Culture & Sports: 41:00–44:55
- Fan Q&A: Ceremony Mishaps: 46:56–50:23
- Fan Q&A: Sleep on Tour: 50:28–55:58
- Fan Q&A: Ohtani Translator: 56:17–58:13
Summary & Takeaways
This episode offered a candid, lively wrap-up of the WTA season — equal parts honesty, humor, and camaraderie. The co-hosts gave fans rare insight into the logistical (and emotional) realities of tennis—a sport where year-end highs and lows blend quickly and tomorrow’s challenge is never far away. Their group dynamic—equal parts self-deprecating, supportive, and witty—keeps things both fun and relatable, whether discussing tournament drama or the mysteries of vacuum-sealing travel pillows.
For anyone who wants an all-access pass to the personalities behind today’s women’s tennis, this episode is a celebration of the human side of sport—mistakes, mishaps, and all.