857. Jackson Olson, Savannah Bananas Infielder & Runner
Release Date: 12/31/2025
Ali on the Run Show
"Winning is really fun!" On Saturday afternoon during Boston Marathon weekend, more than 775 of us took over The TRACK at New Balance for a super fun live show with cohosts Eric Jenkins and Aisha Praught Leer. No further intro needed. SPONSOR: New Balance. to check out the brand new Ellipse, New Balance's just-released everyday trainer. (It's gorgeous!) Follow Ali: SUPPORT the Ali on the Run Show! If you’re enjoying the show, please . Spread the run love. And if you liked this episode, share it with your friends!
info_outlineAli on the Run Show
"I have severe FOMO. All I want to do is run this marathon on Monday." Claire Holt is an actress best known for her work on Pretty Little Liars, H20: Just Add Water, The Vampire Diaries, and Mean Girls 2. She's a mom of three who lives in Miami. And she is a runner and a marathoner. Claire came to Boston to do this live show with us, and to take in all the weekend vibes, and I think it's safe to say she'll be back. Biggest thanks to Shokz for supporting this episode and for making all this magic happen, and thank you to Steven and the amazing team at WBUR CitySpace for having us. FOLLOW CLAIRE...
info_outlineAli on the Run Show
"I went back to Boston, and I found myself again. I found the Ali I knew was in there. The Ali who lives and breathes running. The Ali who had felt so isolated for so long, but who craves community and connection, and knows exactly where to find it." We're just days away from the 130th Boston Marathon! Last year, I was honored to be asked to be the keynote speaker at the Boston Athletic Association's annual partner summit at the Museum of Science. I used the opportunity to share my Boston Marathon story. My story, as someone who grew up 80 minutes north of Boston, who knew nothing about the...
info_outlineAli on the Run Show
"Doubt and belief can coexist. In the book, you see a ton of my doubts and struggles with confidence. But then there’s also this untouchable belief that’s always there, too. So it’s almost like, which voice are you going to listen to?" It's a big week for professional runner Sara Hall! She turns 43 tomorrow, and then heads east to race the Boston Marathon on Monday. And while most marathoners are recovering on Tuesday, Sara, in true Sara form, will be doing the opposite: It's book launch day! Sara's debut memoir, , comes out April 21, and in this conversation, Sara talks about why...
info_outlineAli on the Run Show
"Calm, calm, calm. Relax, relax, relax." Welcome to your guide to the 2026 Boston Marathon! We just about one week away from the 130th running of the world's oldest marathon. This year's Boston Marathon takes place, as always, on the third Monday of April — this year, that's April 20. In this mega-episode, I (along with a team of experts and insiders) attempt to answer all of your questions about all things Boston. Katie Hawkes and Lauren Proshan from the Boston Athletic Association are here to talk logistics (take some deep breaths — the journey to the start line is doable, and you...
info_outlineAli on the Run Show
"That’s been my thing lately: What excites me?" Emily Sisson is the American record holder in the marathon, a two-time Olympian, and a New Balance professional athlete. And right now, she's gearing up to make her Boston Marathon debut. In this conversation, Emily talks about how the Boston build has been going, and why now was the time to finally race Boston. She talks about her sixth-place finish at last month's United NYC Half, explains why she wanted more from her 2:25 finish at the New York City Marathon in the fall, and talks about making Ireland home — and making new friends in the...
info_outlineAli on the Run Show
"All I can do is move forward knowing that one day I’ll have that moment." Jess McClain just might be the most-loved professional marathoner in the country. The Phoenix, AZ-based Brooks athlete made national headlines last month when she was leading the U.S. Half Marathon National Championships in Atlanta and was led off course by an official vehicle in the final mile of the race. That day, Jess lost out on a national title, a spot on Team USA, and a good amount of prize money. (Listen to Emma Grace Hurley's recap of the day .) She handled the aftermath with grace, compassion, and optimism....
info_outlineAli on the Run Show
"It’s a new day, it’s a new age, let’s learn, let’s grow together. That’s it." Last week, professional Colorado-based marathoner Emma Bates when she shared that she had been dropped by her fueling sponsor after they found out she was pregnant. In this conversation, Emma shares her side of the story that has taken the running community by storm. Emma also talks about running a 2:25 at the Valencia Marathon in the fall, about finding out the next day that she was pregnant, and about the realities of being a pregnant professional marathoner. SPONSOR: Lagoon. to...
info_outlineAli on the Run Show
"I needed to do it like I needed to breathe." At any given marathon, there are thousands of runners on the start line, hoping to complete the 26.2-mile journey to the finish line. That means that at any given marathon, there are thousands of reasons to run. This episode is about those reasons. (Thank you to the nearly 1,000 of you who shared the stories behind why you ran your first marathon. Truly inspiring.) SPONSOR: Oofos: The best in the recovery footwear game. to check out Oofos's new CLUB+ line! Your feet are going to be so happy! In this episode: Why I ran *my*...
info_outlineAli on the Run Show
I remember being like, 'I can’t believe I’m here. I can’t believe I’m doing this right now.'" It's been a while since I've done a race recap! This weekend, I ran the United Airlines NYC Half — my first half marathon in two years. With 11 rounds of chemotherapy in the rear view, I felt a major shift this weekend in my favorite city, with so many of my favorite people, doing one of my favorite things. In this solo episode, I'm breaking down the entire weekend (in far too much detail, and with too many stories about parking, turkeys, and eyebrow tinting). From the parties and plays to...
info_outline"I think there are a lot of athletes out there that are just so scared to show who they truly are and what they like because of their teammates and their coaches. And they’re trying to get to the next level, and they’re like, 'Oh well, if I like this then I’m not gonna get to the next level.' It’s actually the opposite. You’re probably gonna play better if you show who you truly are, because you’re more free."
Everyone loves Jackson Olson. The Savannah Bananas infielder is on a mission to make baseball more fun — and he's doing just that. Jackson has made a name for himself playing Banana Ball, which is like the baseball version of the Harlem Globetrotters. The exhibition-style games include full-on performances with choreography, lip syncing, and walk-ups designed to delight the sold-out stadium crowds. In this conversation, Jackson talks about his road to the Bananas, and his road to becoming a runner. This fall, Jackson ran his first race — the Disney Wine & Dine 5K — and now he's training for a 10K in January while figuring out how running fits into his busy baseball season. Plus, talking Taylor Swift, Disney World, and how Jackson found his voice and his confidence.
FOLLOW JACKSON @jacksonolson_
SPONSOR:
- New Balance: Click here to get your hands on the fan favorite Rebel v5!
In this episode:
- On identifying as a runner (2:40)
- Jackson shares the journey to his first 5K, and his impressions of the running community (5:00)
- Why Jackson turned down an offer to go pro out of college (13:55)
- How Jackson learned to embrace his Disney-loving Swiftie side (20:40)
- How Jackson became a Savannah Banana (29:30)
- All about the theatrics behind the Bananas, including how Jackson pulled off his “Life of a Showgirl” walkup the day after The Life of a Showgirl was released (34:45)
- What it was life living out a childhood dream: playing at Yankee Stadium (43:25)
- Taylor Swift talk! (48:30)
- Will we see Jackson on Dancing With the Stars? (58:00)
- How Jackson is feeling heading into this season with the Bananas (1:02:00)
Follow Ali:
SUPPORT the Ali on the Run Show! If you’re enjoying the show, please subscribe and leave a rating and review on Apple Podcasts. Spread the run love. And if you liked this episode, share it with your friends!