The Bert Show – “This Letter From Bert's Big Adventure Kid Jameson's Mom Will Melt Your Heart”

Air Date: February 23, 2026
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, et al.)
Special Focus: The heartfelt letter from Jameson's mom during Bert’s Big Adventure

Episode Overview

This episode captures the magic, joy, and deep emotion of Bert’s Big Adventure—a special trip for children facing health challenges and their families. The focus is on Jameson and his family, their memorable experience at Disney, and a moving letter written by Jameson's mom. It’s a segment filled with humor, gratitude, emotional vulnerability, and celebration of resilience.

Key Discussion Points & Insights

The Pin Game & Disney Traditions

• Pin Collecting Mishap

  • Bert recounts promising Jameson he’d be the “pin king” at Disney, helping him get as many collectible pins as possible.
  • Despite their efforts, another child (Gunner) ends up with even more pins, creating a funny and relatable moment.
  • [03:22] Bert: “I make a promise to him... you're gonna have the most pins... you are gonna be the pin king, right?”
  • This leads to a gentle, humorous apology when Bert’s promise doesn’t pan out as expected.
  • [04:34] Bert: “How dare you? And I looked at him like, I am so sorry. And it's Dr. Michelle's fault.”

• Favorite Pins & Disney Experiences

  • Jameson’s favorite pin is the Aladdin one.
  • There’s discussion about the joy of trading pins, commemorating epic moments, and how these traditions build community at Disney.
  • [04:54] Co-Host Question: “Which one's your favorite, Jameson?”
  • [04:54] Jameson's Mom: "The Aladdin one."

• The Giant Stitch Plush

  • Jameson receives a massive Stitch plush, a recurring theme where a volunteer seeks out a child to gift the largest Stitch toy each year.
  • Stitch accompanies Jameson to dinner and a movie, delighting both him and those around.
  • [06:17] Volunteer: “It’s kind of my thing every year, to get a massive stitch that’s bigger than they are... and what was funny about Jameson is... Stitch had a seat, ate dinner with us, and then we were watching the movie. He had Stitch kind of sitting around him as his buddy, watching his favorite movie with him, which I thought was really sweet.”

Jameson’s Big Role & Family Joy

• Jameson as Children’s Miracle Network Ambassador

  • Jameson serves as an ambassador, sharing his story to support fundraising for other children’s programs.
  • [07:09] Jameson's Mom: “He’s an ambassador... for 2025, 2026 to represent and just goes to different locations... to tell his story and let [people] know what they are donating for and what it goes towards.”

• Surprises & Magical Memories

  • The family reflects on having no expectations and being thoroughly blown away by the experience.
  • Andre (family member) recalls seeing another child admiring Jameson's pin collection with awe.
  • [08:16] Andre: “I see this kid look over at Jameson and then he taps his sister, and then he goes, ‘Dude, that kid is stacked.’”
  • The unpredictable joy of Disney moments—unexpected rides, desserts during fireworks at a “veranda,” and a special after-hours Ratatouille ride.

The Heartfelt Letter from Jameson’s Mom

The emotional centerpiece of the episode

• Jameson’s mother reads her letter aloud, reflecting on his health journey, his resilience through heart and throat surgeries, and how he never lets obstacles define him.
• She expresses immense gratitude for the experience provided by Bert’s Big Adventure, highlighting the importance of family moments and the unique peace she felt knowing everything was handled and her kids were happy together.
• Notable Excerpts:

  • [09:25] Jameson's Mom:
    "My sweet Jameson, from the moment I found out I was pregnant with you... we learned about your heart defect... Your life has been nothing short of surprises. No matter what has been thrown your way, we have always found a way through it together. Watching you grow has been one of the greatest blessings of my life."

  • [10:09] Jameson's Mom:
    "Even with these obstacles, you never let them define you or hold you back. That kind of strength cannot be taught. It comes from deep within. And I'm so proud of you."

  • [11:21] Jameson's Mom:
    "As your mom, that means more to me than I can ever explain. Seeing all of you laugh together, try new things, and share in a once in a lifetime experience is something I will treasure forever."

  • [12:13] Jameson's Mom:
    "You have faced more in your young life than many people will ever face, and you continue to rise above it with courage, kindness, and strength. You inspire me every single day..."

  • Sign off with love:
    [12:15] "Love you, piggy."

Reflections on Jameson’s Shyness & Growth

• Bert gently teases Jameson’s supposed shyness, saying he wouldn’t have pegged him as shy given how much he participated and came out of his shell during the trip.
  • [13:10] Bert: “If you'd have lined up 100 words describing him, I had to put shy at the very end of that thing because I haven't seen that at all.”
• Jameson’s mom and family discuss how he adapts in new situations—quiet at first but opening up with friendly encouragement and support.

Memorable Quotes & Moments

• [03:22] Bert: “You are gonna be the pin king, right?”
• [06:17] Volunteer: “…Stitch had a seat, ate dinner with us, and then we were watching the movie… I thought that was really sweet.”
• [07:09] Jameson's Mom: “He’s an ambassador... to go and tell his story...”
• [08:16] Andre: “Dude, that kid is stacked.”
• [09:25-12:15] Jameson's Mom: The full heartfelt letter, including:
  • “You inspire me every single day, which is why I’m able to advocate for you like I do. I love you more than words could ever explain. Love you, piggy.”
• [13:10] Bert: “If you'd have lined up 100 words describing him, I had to put shy at the very end…”

Important Segment Timestamps

• [02:00-03:51] – Pin collecting and the “pin king" promise
• [04:47-05:10] – Jameson's favorite Disney moments
• [05:55-06:52] – Giant Stitch plush story
• [07:09-07:46] – Jameson as Children’s Miracle Network ambassador
• [08:16-09:15] – Family reflections and memorable moments
• [09:25-12:15] – Jameson's Mom’s letter (emotional highlight)
• [12:19-13:24] – Family talks about Jameson’s shyness and growth

Summary

This episode stands out for its authenticity, warmth, and powerful depiction of family resilience. Listeners get an intimate look at Jameson’s journey through his family’s eyes, feel the fun and camaraderie of Bert’s Big Adventure, and hear directly from a mother’s heart about the life-changing impact of kindness, adventure, and acceptance. The Bert Show team brings together humor, sincerity, and support, making this episode both moving and deeply memorable.