A Canadian Legend in The American Civil War.

In this episode of Canada Is Boring, Rhys and Jesse explore the wild, stranger‑than‑fiction life of Emma Edmonds, a Canadian who fought in the American Civil War while living under multiple identities. Born in 1841 in rural New Brunswick to a harsh, domineering father obsessed with having “strong sons,” Emma grows up physically capable, adventurous, and deeply resentful of male tyranny. Inspired by a pulp adventure about Fanny Campbell, a girl who disguises herself as a man to rescue her lover from pirates, Emma refuses an arranged marriage at fifteen and runs away to work in a millinery shop. Within a year she becomes a co‑owner, but when her father tracks her down, she disappears completely—re‑emerging as Frank Thompson, a Bible salesman.

As Frank, she becomes a remarkably successful door‑to‑door Bible seller and eventually heads to the United States. When the Civil War breaks out, she volunteers for the Union Army, initially rejected for being too short but later accepted once standards drop. Posing as a male recruit, Frank Thompson serves as a nurse and postman, moving through brutal campaigns like Bull Run, where Emma witnesses the gore and chaos of battle firsthand. Her competence and toughness help her blend in with city boys unused to outdoor life, while Victorian modesty norms make it easier to keep her true identity hidden.

Emma’s war story escalates when she volunteers to replace a hanged Union spy. Under a series of disguises—posing as an enslaved Black labourer, an Irish immigrant, a Black woman, and even a Confederate trooper—she repeatedly infiltrates Confederate lines, gathering intelligence, sketching fortifications, and even cooking within sight of General Robert E. Lee. At one point, she’s conscripted into a Confederate cavalry unit against her will and uses a panicked horse as cover to “accidentally” cross back to Union lines. In one of the story’s most surreal moments, she comforts a dying “male” soldier who reveals she too is a woman who enlisted to stay close to her brother.

Eventually, Emma contracts malaria. Unable to check into a military hospital without exposing her secret, she travels to Pittsburgh, puts on a dress, and is treated as a woman before quietly trying to rejoin her unit. When she discovers that Frank Thompson has been declared a deserter—a crime punishable by death—she disappears again, this time returning to Canada.

00:00 – Winter hibernation and opening banter
00:30 – Introducing the American Civil War & “Mulan” comparisons
02:23 – Canada, Cuba travel and setting up the episode
03:22 – Canada as a haven for escaped slaves & Civil War context
04:06 – Emma’s harsh childhood in New Brunswick
06:04 – Tomboy Emma and early adventurous streak
06:31 – Fanny Campbell and inspiration to run away
07:47 – Arranged marriage, patriarchy and gender roles
08:47 – Running away to make hats & becoming a co‑owner
09:23 – Assuming the identity of Frank Thompson
10:36 – Life as a Bible salesman & door‑to‑door culture
11:48 – 90s nostalgia: encyclopedias, dictionaries and pre‑internet life
13:29 – Shared reality vs today’s fragmented information world
14:09 – VHS rentals, Blockbuster and small‑town video stories
16:04 – Jesse’s dream video‑store café/bar concept
16:15 – Emma heads to Flint, Michigan and joins the Union Army
17:01 – Passing the “firm handshake” physical and army life
17:49 – Training, modesty and hiding her identity
18:44 – Ad break: “Canada Is Boring” Patreon plug
19:26 – Comedy detour: Blackadder and gender‑disguise tropes
20:21 – Spy work begins: disguises and infiltration as a slave
24:16 – Risks, labour, and moving around Confederate camps
26:01 – Escaping back to Union lines and reporting intelligence
27:10 – Layers of disguise: woman as man as woman again
28:20 – Cooking near Robert E. Lee & more spy missions
29:47 – Discovering another disguised woman soldier on the battlefield
31:03 – Spy work in Kentucky and accidental Confederate conscription
32:27 – Using a panicked horse to cross back to Union lines
32:53 – Infiltrating a Confederate spy ring in Louisville
33:29 – Malaria, hospital in a dress, and “Frank Thompson” the deserter
34:50 – Returning to Canada and marrying Linus Seely
35:54 – Post‑war recognition, pension and veteran honours
36:23 – Emma’s legacy in the Grand Army of the Republic
37:05 – Episode wrap on Emma Edmonds’ life
37:14 – Entering the Small Talk Dimension (STD Zone)
38:01 – News, looming civil war vibes and feeling depressed
39:04 – Trump’s need to “rate” every conversation and letter
41:08 – Jesse’s A/B testing theory of Trump’s communication
41:49 – Trump’s “peace board” and billion‑dollar memberships
43:07 – 500th episode speak pipes and editing the celebration
44:12 – The missing SpeakPipe link confession
44:19 – Gratitude for listeners and looking to 500 more episodes
44:38 – Closing theme: “Canada Is Boring” song