The Ebro, Laura, Rosenberg Show — Episode 50

"CC Sabathia Talks Jersey Retirement + Lena Waithe on 'Trinity' + Family Matters"

Date: March 6, 2026
Hosts: Ebro Darden, Laura Stylez, Peter Rosenberg

Episode Overview

This episode features a deep dive into the journeys and current projects of two acclaimed guests: MLB legend CC Sabathia, reflecting on his impact and upcoming Yankees jersey retirement, and creator-writer-performer Lena Waithe, discussing her foray into stage with the play "Trinity" and her reflections on legacy and community. The hosts round out the show with a heartfelt, funny "Family Matters" segment, sharing relatable parenting and life stories with their families and audience.

The tone is genuine, celebratory, and real—a blend of camaraderie, cultural insight, and community laughter characteristic of the ELR show.

Key Topics & Discussions

1. CC Sabathia: Yankee Legend, Legacy & Giving Back

[1:35 - 23:32]

CC's Achievements and Accolades

• CC’s backdrop: Warren Spahn trophies, his favorite, awarded to best left-handed MLB pitcher ("I think I won it 2007, 8 and 9. It's a pretty cool trophy... That's probably my favorite." — CC Sabathia, 02:06)
• Cy Young plaque now in Cooperstown

Reflecting on his Yankees Journey

• On being honored with jersey retirement:

  "I mean, you know, you’ve been... a part of the journey since we got here in, in 2008. To be completely honest, I think everybody knows the story by now, but I didn’t want to come here. This wasn't my first choice..."
  — CC Sabathia, 03:59

• Initial reluctance to come to NY, fears of harsh media and fan scrutiny, longing for home in California
• Cashman’s role: "He was so bullish on this, and I know you'll love it here. If you don't like it in three years, you can leave. But I promise you'll want to stay."
  — CC Sabathia, 06:12

NY Fan Culture, Grind, and Championship Pressure

• Respect for relentless NY fans: "They might talk a little ish to you... but there’s always love." — Laura Rosenberg, 05:59

• Hard work and honesty: "The fans appreciated everything I gave out on the field every fifth day." — CC, 06:12

• 2009 championship impact:

  "When you come here, that’s all you hear about – the championships... I remember sitting there and Juan [Jay Z’s friend] was like, you need to win a championship right now... The championship was something that I was really worried about. I thought for my career, you're going to be like Karl Malone or Charles Barkley, have all these numbers and never have a ring." — CC Sabathia, 07:59

• On pressure for current players (e.g., Aaron Judge):
  "I feel like the one person that can really talk to him or understand what he’s going through is Alex [Rodriguez]... it didn’t matter until he hit in the playoffs in 2009." — CC, 09:55

Community, Foundation, and Representation

• Pitch In Foundation origins:
  "We started a Pitch In Foundation 2006, like, in our living room in California... starting with renovating that [local] field, and then we've been renovating fields from California, you know, across the country, in Ohio, in the Bronx." — CC, 10:56
• Focus: Backpack giveaways, field renovations, community Little Leagues, helping Black youth access baseball
• The Players Alliance:
  "With TPA, we’re trying to make sure that people can stay in their community, grow up and play the game of baseball and still be able to have a chance." — CC, 15:34

Legacy, Critics, and the Monument Park Moment

• On media critics (esp. Phil Mushnick’s column doubting his Monument Park credentials):
  "Who is Phil Mushnick? I’ve never heard of this guy until the other day... he’s never been around the clubhouse... it makes no sense to me." — CC, 19:17
• Respect for true clubhouse writers:
  "Joe Sherman... will write something about you and then come stand right next to your locker the next day. That’s the guy that you got to give respect to." — CC, 21:27
• “If I look at my career as a totality and if everything was here in New York, then it would be no problem with me going into Monument Park. If you look at my whole career...” — CC, 22:29

Memorable Quotes

• "I think people understood every time I went out, I wanted to try to win. I was doing everything I could to win." — CC, 06:12
• "It may be only me and Reggie [Jackson] that are the ones that ended up in Monument Park signing the free agent deal." — CC, 23:01

2. Lena Waithe: "Trinity," Art as Healing, and Cultural Legacy

[28:01 - 41:19]

Trinity: New Stage Play at Baltimore Center Stage

• Title reflects: parental, platonic, romantic relationships
• On the play's premise:

  "It’s really about how our relationships—our platonic relationships, our romantic relationships—are directly affected by how we were raised... It’s about those three different relationships... That’s the trinity."
  — Lena Waithe, 29:19

• "It's a bit of a therapy session, but it's funny, it's entertaining... A trendy playlist—Stevie Wonder, Kehlani, Leon Thomas, Duke Ellington..." — Lena, 30:08
• Three-person cast, futuristic staging

Why Theater, Why Now?

• Never performed or written for the stage before:
  "This is my first time acting on stage. It's my first time writing a play." — Lena, 31:13
• Draw to theater as phone-free, deeply communal art form:
  "In theater, pulling out your phone is like pulling out a cigarette on an airplane... It’s ill advised." — Lena, 31:29
• "I just want to pay homage to... someone like Felicia, who did Soul Food, the series on Showtime, where we wouldn't be here were it not for that show." — Lena, 37:37

Reflections on "The Chi" Ending

• Season 8 = Final season, deep gratitude for long arc and cast's growth
• “The Shy says goodbye, season eight... I’ve never done a last season of a show before... I’m just in a space of gratitude to have been on for eight seasons, to have grown so much.” — Lena, 36:39
• "The syndication checks aren’t what they used to be... I still gotta go to work. I may be on YouTube with y’all." — Lena, 38:36

Cultural Labor, Transition, & Community

• Recognizing intergenerational work:
  "There have been so many people that have come before me that are the reasons why I am here right now, why I do what I do." — Lena, 37:37
• On performing emotionally vulnerable work: "We say there’s emotional nudity in the play, and there is... The audience is another cast member for us." — Lena, 34:34

Notable Quotes & Moments

• "No one is above, no one is below. Anyone... I have to give it my all, because the work is so—I'm on an assignment. It's mission work." — Lena, 33:20
• "I love, like, watching y’all here on this platform on YouTube... Had no issue following y’all over here at the Joy hearing y’all talk about your families and what’s going on." — Lena, 40:33

3. Family Matters: Parenting, Identity, and Family Stories

[41:20 - 69:19]

Issa Makes a Surprise Appearance

• Issa (Ebro’s daughter, age 11) guest stars, shares about her international youth flag football tournament in Florida—team finished strong, played on ESPN, describes tournament nerves and fun.
• Navigating being a big sister, sibling dynamics ("She picks and chooses when she wants to be nice to you." — Issa, 45:53)
• Reflections on managing younger siblings with school and hobbies, balancing her own pursuits
• Funny retelling of tween drama at a Freya Sky concert:

  "I'm not that rat. Being an adult is hard."
  — Issa, 55:56

Parenting Real Talk

• Hosts swap real-life family logistics, joys, tradeoffs, and the emotional realities of parenting from birth to the teenage years and beyond.
• Honest reflections on choosing family size:
  "Some people just want to go back to being able to do the things they love to do... it’s not selfish." — Fetna, 63:59
• Rosenberg contemplates timing for a second child, juxtaposed with partner’s career comeback
• "You're not selfish for wanting to have a life for yourself." — Ebro, 64:12
• Discussion on the phases of parenting: newborn sacrifices, scheduling, anxiety of kids growing up ("There are people that when their kids get to be high teenagers, it's so difficult... My dad never slept on Saturday nights until he heard that door slam." — Rosenberg, 66:02)
• Extended family photo nostalgia: hosts and Issa reminisce over childhood photos, birthdays, and changing family milestones

Community Announcements

• Birthday shoutouts, comments on team members’ growing families, and solidarity for all in the trenches of both parenting and "merch shipping"
• On partnership: "Her job is... But you have a job in this too. That's important." — Ebro to Laura and Rosenberg, 68:23

Notable Quotes Section

“I appreciate it because, I mean, I think you know, you’ve been... a part of the journey since we got here in 2008. And to be completely honest, I think everybody knows the story by now, but I didn’t want to come here. Like this wasn’t my first choice.”
— CC Sabathia, [03:59]

“The fans appreciated everything that I gave out on the field every fifth day... I think people understood every time I went out, I wanted to try to win.”
— CC Sabathia, [06:12]

“Trinity is really about how our relationships—our platonic relationships, our romantic relationships—are directly affected by how we were raised. And it’s about going back to the beginning and figuring out what our mothers and our fathers taught us about love...”
— Lena Waithe, [29:19]

"The audience is another cast member for us."
— Lena Waithe, [36:22]

“Being an adult is hard.”
— Issa, [55:56]

Important Timestamps & Segments

| Time | Segment | | ---------- | ------------------------------------------------------- | | 01:35 | CC Sabathia joins, discusses trophies, Yankees legacy | | 03:59 | CC reflects on journey to Yankees, hometown loyalty | | 05:40 | Discussion: NY hustle, fan respect, adapting as a star | | 07:59 | 2009 title, championship pressure and legacy | | 10:56 | CC’s Pitch In Foundation, community projects | | 15:34 | The Players Alliance, making baseball more inclusive | | 19:17 | Media critics, legacy, Monument Park | | 23:32 | Goodbye to CC, host banter, legacy wrap | | 28:01 | Lena Waithe joins — "Trinity," artistic vulnerability | | 31:13 | Lena's theater debut and creative process | | 36:39 | Reflecting on "The Chi" and the power of cultural legacy| | 41:20 | "Family Matters" segment: family stories, Issa’s sports| | 55:56 | Issa’s relatable tween concert drama | | 63:50 | Parenting choices, self-care vs. sacrifice debate | | 66:02 | Teen stress, multigenerational parenting | | 68:38 | Merch shop banter, team shoutouts |

Overall Episode Mood & Value

This episode blends intimate reflections on legacy, vulnerability, and community engagement—with laughter, support, and realness interwoven throughout. For new or loyal listeners, it's a masterclass in cultural and generational dialogue, spanning sports, the arts, and family life.

If you missed it:
You'll walk away understanding not just why CC Sabathia and Lena Waithe are respected cultural icons, but also how their journeys intersect with community, vulnerability, and the evolving realities of family—on and off the field and stage.

End of Summary