Sergeant Stubby: A Very Good Boy Goes to War

    How a stray dog became the unofficial mascot of World War I

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    Episode Summary

    In this heartwarming episode of "Rainy Day Rabbit Holes," hosts Shay and Jody take listeners on a captivating journey through the life of one of World War I's most unlikely heroes: Sergeant Stubby, the Boston Terrier who became a symbol of courage and loyalty on the battlefields of France. Amidst the chaos of gas attacks, trench raids, and the deafening sounds of artillery, Stubby not only survived but thrived, leaving an indelible mark on military history.

    The episode begins with a vivid backdrop of World War I, painting a picture of the harsh realities faced by soldiers—including Corporal James Robert Conroy, Stubby’s best friend and fellow soldier. Conroy, who enlisted at the age of 25, formed an unbreakable bond with Stubby after the little dog wandered onto the military grounds at Yale University during training. The hosts delve into the emotional history of Conroy, an orphan who lost both parents at a young age, highlighting how those early experiences shaped his character and loyalty—not only to his comrades but also to his canine companion.

    As Stubby becomes the unofficial mascot of the 102nd Infantry Regiment, listeners learn about his endearing antics and impressive skills. From marching in step with the troops to performing salutes, Stubby quickly became a beloved fixture among the soldiers, boosting morale during some of the war's darkest moments. When Conroy and his unit were deployed to France, he smuggled Stubby aboard, showcasing the lengths to which they would go for their friendship.

    The episode captures the tension of combat as Stubby faced mustard gas attacks, demonstrating his remarkable ability to detect danger. His keen sense of smell became an early warning system that saved countless lives, a testament to the loyalty and bravery that define his legacy. With gripping storytelling, the hosts recount a particularly harrowing night when Stubby alerted the troops to an impending gas attack, showcasing his instinctual understanding of danger.

    Listeners are treated to tales of Stubby’s many heroic deeds, including locating wounded soldiers in no man's land and thwarting a German spy’s plans. Each story reinforces the idea that heroism comes in many forms and that even the smallest warriors can make a monumental difference.

    As the episode progresses, Stubby’s fame grows, leading him to meet Presidents Woodrow Wilson and Calvin Coolidge, partake in parades, and even earn a military rank—becoming the first dog to be promoted to sergeant in U.S. history. His journey from a stray dog to a decorated war hero captivates the audience, evoking a sense of pride and nostalgia for a time when loyalty and love transcended the brutality of war.

    In a poignant conclusion, the hosts reflect on the life lessons that Stubby's story imparts: the importance of showing up for those we care about, the power of loyalty, and the profound love that dogs bring into our lives. With humor and sensitivity, they remind us that while we may not be able to change the world, we can certainly make a difference in the lives of those around us—just like Sergeant Stubby did.

    Join Shay, Jody, and their special guest Erin as they celebrate this remarkable canine hero in an episode filled with laughter, tears, and heartfelt admiration for the unsung heroes of history. Tune in to "Rainy Day Rabbit Holes" and discover the incredible story of Sergeant Stubby—an adventure that proves that even in the darkest of times, love and loyalty can shine through.

    In the chaos of World War I, one unlikely soldier refused to stay behind. He didn’t carry a rifle, didn’t understand borders or politics, and technically wasn’t allowed to enlist—but he charged into danger anyway.

    In this episode, we tell the true story of Sergeant Stubby, a Boston Terrier mix who became one of the most decorated heroes of World War I. From smuggling himself onto a troop ship, to warning soldiers of mustard gas attacks, locating wounded men in no man’s land, and even capturing an enemy spy, Stubby proved that bravery doesn’t require rank—or even thumbs.

    Joining us for this emotional (and occasionally unhinged) journey is special guest Erin, Shea’s longtime friend and fellow history nerd, who helps us explore why Stubby’s story still resonates more than a century later.

    Fair warning: this is a dog story, which means Shea cries. More than once. We apologize in advance—and also refuse to apologize at all.

    🐾 In This Episode:

    • How a stray dog became the unofficial mascot of the 102nd Infantry Regiment
    • Sergeant Stubby’s role in 17 battles on the Western Front
    • Mustard gas detection, artillery warnings, and battlefield rescues
    • The night Stubby captured a German spy—and earned a promotion
    • Stubby’s postwar celebrity life, medals, and legacy
    • Why this small dog’s story still hits so hard today

    🎖 Notable Figures:

    • Sergeant Stubby – World War I war dog and certified good boy
    • Corporal James Robert Conroy – Stubby’s human best friend and handler
    • Erin – Special guest, history nerd, and longtime friend of Shea

    You can find photos, sources, and more stories like this at

    👉 https://rainydayrabbitholes.com



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    March 25, 2026

    Episode Gallery

    Sergeant Stubby: A Very Good Boy Goes to War episode image

    Sergeant Stubby: A Very Good Boy Goes to War episode image

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    Corporal James Robert Conroy and Stubby

    Corporal James Robert Conroy and Stubby

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    Sources and Links

    • Wikipedia

      https://en.wikipedia.org/wiki/Sergeant_Stubby

    • Connecticut Military Department

      https://portal.ct.gov/mil/mapo/history/people/stubby-the-military-dog

    • Connecticut History.Org

      https://connecticuthistory.org/a-true-dog-of-war-sergeant-stubby/

    • America Comes Alive

      https://americacomesalive.com/sergeant-stubby-1916-or-1917-march-16-1926-world-war-i-mascot/

    • History Extra

      https://www.historyextra.com/period/first-world-war/sergeant-stubby-richard-lanni-film-animated-war-dog-american-history/

    Episode Location

    Germany

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