The Lovable Reunion Podcast
Episode: David Ross & Anthony Rizzo Kick Off 2016 Chicago Cubs World Series Podcast
Date: March 31, 2026
Hosts: Anthony Rizzo & David Ross
Location: Recorded at Murphy's Bleachers, Wrigleyville, Chicago
Episode Overview
To mark the 10th anniversary of the Chicago Cubs’ historic 2016 World Series championship, Anthony Rizzo and David Ross kick off “The Lovable Reunion” podcast. The series promises behind-the-scenes clubhouse stories, untold perspectives, and heartfelt reflections from the players and coaches who ended the legendary 108-year drought. In this engaging first episode, Rizzo and Ross share their personal journey, memorable team moments, leadership lessons, the emotional ride of the postseason, and the enduring bond with Cubs fans.
Key Discussion Points & Insights
1. Reflecting on 10 Years: Life After 2016
- Both hosts catch up on their post-2016 lives and careers, with Rizzo becoming a Cubs ambassador, doing baseball media, and Ross transitioning into management and post-playing life.
- Quote (Ross, 01:34): “Ten years has gone by. I feel like it’s happened so fast. Our kids… everybody's kids have gotten older and grown up… it's nuts how fast the 10 years has gone.”
- Both hosts mention the Cubs Convention reunion and marvel at time’s passage.
2. How Rizzo & Ross Met and Became “Brothers for Life”
- Recounting their first meeting in 2008 when Rizzo, undergoing cancer treatment, received a ticket from Ross (then with the Red Sox).
- Quote (Rizzo, 02:12): “Turns out, we’re brothers for life. Turns out… that was kind of crazy, the fact it went full circle.”
- Their “real” first bonding came at an ESPN car wash in 2014, leading Rizzo to lobby for Ross to join the Cubs, setting up foundational team chemistry.
3. Building a Championship Culture
- Ross & Lester’s leadership raised team professionalism upon arrival.
- Quote (Rizzo, 08:03): “They elevated me personally to another level of professionalism. It was all about winning—what it took to win, the energy it takes to win.”
- Ross’s philosophy: the “shit sandwich” approach to feedback.
- Quote (Ross, 06:48): “You start with a real positive thing, you say the shitty stuff in the middle, and you end with some positivity.”
- Rizzo’s specific anecdotes about learning respect for bench players and always being present (“I took that with me for the rest of my career.” – 15:09).
4. Defining Moments Before the Breakthrough
- Sweeping the Giants in August 2015 as a turning point (“That series really stood out…” – Ross, 09:59)
- The parties, karaoke at Stanley’s, night in Lester’s penthouse—team-building that fostered trust and looseness.
5. Leadership, Accountability & Camaraderie
- Memorable “calling out” moments:
- Ross confronting Rizzo after a rough, hungover start in Pittsburgh (12:46–14:14)
- Learning from veterans and holding each other accountable.
- Quote (Rizzo, 14:15): “For the rest of my career, any day I had off, I was out there for first pitch watching those guys.”
- The importance of showing up for teammates and recognizing the role of both stars and role players.
6. The 2015–16 Transition & Mindset
- The feeling of being “America’s team” (28:52), handling “embrace the target” mentality, and lessons learnt from falling short in 2015.
- The off-field rituals—Vegas, penthouse sharing, mimosa and Bloody Mary bars before spring training games, wild nights, and the looseness Joe Maddon championed.
7. Rituals, Inside Jokes, and Grandpa Rossi
- Grandpa Rossi Instagram account, clubhouse handshakes, and unique team rituals that helped them “keep the mood light but focused."
- Quote (Ross, 19:47): “Joe let us have those moments and the off-the-field stuff, and he championed that. Talking about embrace the target...”
8. 2016 Playoff Run – Critical Moments
- Giants Division Series: The iconic backpick play and trusting teammate’s baseball IQ (33:17–34:38).
- Dodgers NLCS: The “goldfish memory” after tough losses (36:30), carrying momentum with key hits, and Kershaw’s HR (“That was a bomb.” – Ross, 36:52).
- Clinching the Pennant: The surreal Wrigley celebration (“We still have a job to do!” – Rizzo, 38:02).
9. The World Series – Emotional Roller Coaster
- Fans & Atmosphere: “Fans were so happy, it really was like...no matter the outcome, one fanbase is breaking their own drought.” (39:08)
- Handling Pressure: Rocky movies on clubhouse TVs, motivational speeches, and pregame rituals.
- Quote (Rizzo, 41:02): “We're putting Rocky I and every Rocky on every single TV…”
- The pregame “dancing naked” Rocky routine—a recurring stress relief, repeated even before Game 7 (46:29–48:42).
10. Game 7: Legacy, Drama & Aftermath
- Lead Changes and Pivotal Moments:
- Raje Davis HR shaking everyone (“That curse is fucking real.” – Rizzo, 57:31).
- Chapman’s gutsy 9th inning turnout; rain delay—the “greatest delay in baseball history” (58:22).
- Jason Heyward’s famed rain delay speech that reset the team’s resolve.
- Extras and the Winning Rally:
- Almora’s legendary tag, Zobrist’s go-ahead double, Miggy’s insurance RBI, and Mike Montgomery recording the final out.
- Ross’s Swan Song:
- Game 7 HR in final career at-bat (54:11–54:49).
- The emotional lifting of Ross on teammates’ shoulders after the final out (66:54–69:35).
- Quote (Ross, 67:33): “How did that all transpire? Cuz I’ve never heard this story.” / (Rizzo, 69:01): “To carry you off the field, it was just like a celebration of the boys and for you.”
11. The Parade & the Fans’ Stories
- Exponential celebrations from the plane ride and wild parties to the legendary parade with 6 million attendees (75:01).
- Personal family stories and gratitude for the generational passion of Cubs fans.
- Quote (Ross, 74:34): “The passion that the fans have when they tell those stories are literally still the same, 10 years later.”
12. Looking Ahead
- Teasing future episodes with teammates and coaches, starting with Joe Maddon.
- The mission of the podcast: preserving the memories, reveling in emotion, and connecting with fans anew.
Notable Quotes & Memorable Moments (with Timestamps)
-
On becoming brothers:
“[Our agents] said just say hi, maybe snap a photo… Turns out, we’re brothers for life.” – Rizzo, 02:12 -
On leadership and feedback:
“It’s a shit sandwich, right? You just… start with a real positive thing, you say the shitty stuff in the middle, and you end with some positivity.” – Ross, 06:48 -
On the pressure and joy of winning:
“Losing is easy in the big leagues. You just… lose, you win a couple, you lose… When you win a lot and you lose, it sucks to lose.” – Rizzo, 08:03 -
On the unique Cubs camaraderie:
“It wasn’t just about winning. It was about doing it with those guys.” – Ross, throughout -
Pittsburgh ‘hangover’ game confrontation:
“If you can't stay out all night and you’re not ready to play, don’t stay out all night.” – Ross, 12:50
“Fuck you, Rossi, I’m always ready to play.” – Rizzo, 13:07 -
100th home run at Wrigley & teammate support:
“The look on my teammates' faces with the 100 home run and the Game 7 home run… those moments you can’t get back.” – Ross, 25:42 -
Yadier Molina recognition:
“I thought that was so cool Yadi realized that moment… and gave you that moment at Wrigley.” – Rizzo, 26:34 -
On the infamous Game 7:
“The world just came to me, and in my head, I’m just like, dude, like, this curse is fucking real.” – Rizzo, 57:30 -
On the rain delay speech:
“Jaehe pulls everyone in. And it was like, that moment for us is… legendary.” – Rizzo, 59:29 -
On carrying Ross off the field:
“To carry you off the field, it was just like a celebration of the boys and for you. And like, how cool was that, bro?” – Rizzo, 69:01
Important Segment Timestamps
- How They Met & Became Friends: 02:12–04:59
- Joining Cubs, Building Team Chemistry: 04:59–08:03
- Leadership & Accountability Stories: 12:46–15:09
- 100th Home Run, Yadier Molina: 25:39–26:52
- 2016 NLDS/NLCS Drama: 32:10–38:02
- World Series Pregame Rituals: 41:02, 46:29–49:08
- Game 7 Recap & Rain Delay: 54:11–62:23
- Winning Moment & Carrying Off Ross: 65:00–69:35
- Fan Impact, Legacy, and Parade: 74:03–76:16
Tone and Takeaway
Rizzo and Ross are candid, playful, and unfiltered, constantly balancing humor and emotion. The stories capture genuine affection, camaraderie, and reverence for their teammates, the organization, and the fans. This opening podcast episode not only memorializes the legendary 2016 Cubs but also offers actionable insights into chemistry, leadership, and what it takes to build a true winning culture.
Next Episode: A deep dive with Skipper Joe Maddon—what made him the leader behind the curse-breaking magic.