Noble Blood: "Sing Me a Song of a Lad That Is Gone"

Host: Dana Schwartz
Release Date: November 18, 2025
Podcast: Noble Blood (iHeartPodcasts and Grim & Mild)

Overview

In this episode, host Dana Schwartz delves into the historical story behind the iconic "Sky Boat Song" and the real-life escape of Charles Edward Stuart, better known as Bonnie Prince Charlie, following the disastrous Battle of Culloden. Through this narrative, Schwartz explores the tension between romantic legend and historical reality, focusing on the fateful events of the Jacobite uprising, Charles's flight, and the quietly heroic role of Flora MacDonald.

The episode draws connections between popular culture (like the show "Outlander"), legend, and historical fact, interrogating how these stories become sanitized and romanticized over time.

Key Discussion Points and Insights

1. The Origins and Meaning of the "Sky Boat Song"

[02:05–05:25]

The "Sky Boat Song," familiar as the theme for "Outlander," evokes the escape of Bonnie Prince Charlie after Culloden.
Robert Louis Stevenson’s 1892 version shifts the focus from a "lass" to a "lad," directly referencing Charles Edward Stuart.
Dana explains:

"The lad that Stevenson was referring to wasn’t just a generic character for a poem. He is a very specific lad. Charles Edward Stuart, or the Bonnie Prince Charlie." [04:01]

2. Royal Succession and the Jacobite Cause

[05:25–12:00]

Detailed background on the deposition of King James II in 1688 for Catholic sympathies and the subsequent rule of William and Mary.
The line of succession: Charles was the direct heir if traditional inheritance were followed.
Catholics and supporters of divine right opposed the Parliamentary shuffle, forming the roots of Jacobite support.

3. Charles Stuart’s Upbringing and Character

[12:00–15:40]

Born in Rome in 1720, Charles was raised amidst the legacy of regnal and religious strife.
His mother, Clementina, was intensely anxious about his Catholic upbringing, with the Pope even intervening to ensure his religious education.
Noted for princely entitlement:

"When he was 13, he physically kicked one of his tutors and threatened to kill him if he tried to discipline him." [14:10]
Despite petulance, Charles grew into a charismatic, handsome figure—an ideal banner-bearer for the Jacobite cause.

4. Charles as a Master of Image and Aspiring Revolutionary

[15:40–21:00]

Charles cultivated a powerful image—arriving to balls in Highland dress and jewels, stoking the romanticism of his cause.

"In modern terms, Charles became a master of his own personal brand." [16:52]
France's reluctant, wavering support; Charles’s impatience led him to act regardless of their hesitations.

5. The 1745 Jacobite Rising – Progress, Failure, and Missed Opportunities

[21:00–25:55]

Initial optimism: Early victories, including at Prestonpans, and the symbolic entry into Edinburgh.
Tensions within the Jacobite leadership: Many favored consolidating in Scotland ("Fortress Scotland") rather than risking an assault on London.
Charles wants to push south, barely winning a council vote.
At Derby, morale plummets when promised English and French support fails to materialize.
Historical irony: London was nearly undefended, “Had Charles and his men marched down, there probably wouldn’t have been enough time for British reinforcements to come in.” [24:20]
The retreat marks a turning point; Charles becomes increasingly despondent.

6. The Battle of Culloden and the Collapse

[25:55–28:30]

Culloden is framed as a decisive and disastrous end for the Jacobites.

“One big mistake was fighting on slow, boggy, flat ground, which allowed the British clear lines of free fire and made the Jacobite soldiers slow on their charge... By the time the Jacobites advanced, Charles almost certainly knew that it was pretty much a lost cause.” [27:09]
Notably grim detail:

“Two of Charles’s messengers did get decapitated by cannonballs one after another, which probably wasn’t great for morale.” [27:26]
Charles is convinced to abandon the field—a reluctant, emotionally impactful act.

7. Charles’s Flight and Flora MacDonald’s Role

[28:30–32:10]

The British offer a £30,000 reward for Charles, making trust a scarce commodity.
Flora MacDonald, from a Protestant family and engaged to a British official, agrees to help Charles, disguised as her maid "Betty Burke."

“She said she helped Charles because he was a human being in need. Years later, she would tell Frederick, the Prince of Wales, that she would have done the same for him.” [30:02]
Tense escapes, including a dangerous brush with military officers in Lady Margaret Macdonald’s home, highlight Flora’s extraordinary composure.
After parting at Portree, Charles continues his flight, including further escapes in disguise and near-fatal mishaps.

8. The Legacy of Flora MacDonald and Romanticization

[32:10–36:45]

Flora is briefly imprisoned but quickly becomes a celebrated figure in England—her bravery co-opted into romantic Scottish folklore.

“By the Victorian era, Flora MacDonald as a figure became woven into a romanticized ideal of Scotland, along with Mary, Queen of Scots and the Bonnie Prince Charlie himself. She was a piece of folklore by that point, almost.” [34:25]
Dana’s incisive commentary on the ways conquered histories get sanitized:

“For the English it’s easier to romanticize the rebels who rose up against them when those figures are safely in the past, posing no real threat to their status quo.” [34:40]

Notable Quotes & Memorable Moments

On Flora’s motivations:

“She said she helped Charles because he was a human being in need. Years later, she would tell Frederick, the Prince of Wales, that she would have done the same for him.” (Dana Schwartz, 30:02)
On romanticizing history:

“An Englishman could read a book or poem about Flora MacDonald, pat himself on the back for appreciating how stirring her small moment of history was in beautiful windswept Scotland, and then continue on enjoying the cultural hegemony of England.” (Dana Schwartz, 34:52)
On what might have been:

“If Charles and his men had done what Charles had wanted and they had pressed ahead, would they have been able to take London? It’s extremely plausible, but of course, they didn’t have that intelligence at the time to know how undefended London was.” (Dana Schwartz, 24:25)

Timeline of Important Segments

[02:05–05:25] – The origins, lyrics, and cultural weight of the Sky Boat Song
[05:25–12:00] – Historical and familial backdrop: The exiled Stuarts and rise of Jacobitism
[12:00–15:40] – Charles’s upbringing, personality, and early rebellion
[15:40–21:00] – The Jacobite campaign: cultivating support and image, foiled plans with France
[21:00–25:55] – Rebellion progresses, tactical dilemmas, and a fateful retreat
[25:55–28:30] – The Battle of Culloden: tactical errors, defeat, and immediate aftermath
[28:30–32:10] – Flora MacDonald's role in Charles’s escape, their journey and near-misses
[32:10–36:45] – Flora's legacy, transformation into legend, and critique of romanticizing rebellion
[35:17–36:45] – Flora’s later life: exile, struggles in America and Canada, return to Skye

Postscript: Flora MacDonald's Life After Charles

[35:17–36:45]

After aiding Charles, Flora married Allen MacDonald, moved to North Carolina, and, during the American Revolutionary War, found herself on the British Loyalist side.
The family endured hardship: Allen was imprisoned, their property confiscated, and their attempts to resettle in Nova Scotia failed due to climate.
Ultimately, they returned to Skye, where Flora lived out her years.

“She’s buried there now, in Kilmer Cemetery, a fitting end after a lot of global travel to spend eternity in the place of which she became an indelible symbol.” (Dana Schwartz, 36:35)

Tone & Style

Dana Schwartz maintains a narrative, dryly witty, and slightly sardonic tone throughout, blending empathy for her subjects with skepticism for the ways in which history is repackaged into legend. Her story is immersive yet questioning, balancing vivid anecdote with thoughtful historical critique.

Summary Takeaway

The episode transcends simple legend to probe the nuances of historical reality: how a prince’s foolish bravado and a young woman’s split-second decision became immortalized and then sentimentalized. By drawing out both the high drama and the small ironies, Schwartz invites listeners to see the real, human stakes that underlie the myths of romantic rebellion.

For listeners of both history and "Outlander," this episode provides both context and critique, charting the gap between what was and what we choose to remember.

Noble Blood: "Sing Me a Song of a Lad That Is Gone"

Host: Dana Schwartz
Release Date: November 18, 2025
Podcast: Noble Blood (iHeartPodcasts and Grim & Mild)

Overview

The episode draws connections between popular culture (like the show "Outlander"), legend, and historical fact, interrogating how these stories become sanitized and romanticized over time.

Key Discussion Points and Insights

1. The Origins and Meaning of the "Sky Boat Song"

[02:05–05:25]

The "Sky Boat Song," familiar as the theme for "Outlander," evokes the escape of Bonnie Prince Charlie after Culloden.
Robert Louis Stevenson’s 1892 version shifts the focus from a "lass" to a "lad," directly referencing Charles Edward Stuart.
Dana explains:

"The lad that Stevenson was referring to wasn’t just a generic character for a poem. He is a very specific lad. Charles Edward Stuart, or the Bonnie Prince Charlie." [04:01]

2. Royal Succession and the Jacobite Cause

[05:25–12:00]

Detailed background on the deposition of King James II in 1688 for Catholic sympathies and the subsequent rule of William and Mary.
The line of succession: Charles was the direct heir if traditional inheritance were followed.
Catholics and supporters of divine right opposed the Parliamentary shuffle, forming the roots of Jacobite support.

3. Charles Stuart’s Upbringing and Character

[12:00–15:40]

Born in Rome in 1720, Charles was raised amidst the legacy of regnal and religious strife.
His mother, Clementina, was intensely anxious about his Catholic upbringing, with the Pope even intervening to ensure his religious education.
Noted for princely entitlement:

"When he was 13, he physically kicked one of his tutors and threatened to kill him if he tried to discipline him." [14:10]
Despite petulance, Charles grew into a charismatic, handsome figure—an ideal banner-bearer for the Jacobite cause.

4. Charles as a Master of Image and Aspiring Revolutionary

[15:40–21:00]

Charles cultivated a powerful image—arriving to balls in Highland dress and jewels, stoking the romanticism of his cause.

"In modern terms, Charles became a master of his own personal brand." [16:52]
France's reluctant, wavering support; Charles’s impatience led him to act regardless of their hesitations.

5. The 1745 Jacobite Rising – Progress, Failure, and Missed Opportunities

[21:00–25:55]

Initial optimism: Early victories, including at Prestonpans, and the symbolic entry into Edinburgh.
Tensions within the Jacobite leadership: Many favored consolidating in Scotland ("Fortress Scotland") rather than risking an assault on London.
Charles wants to push south, barely winning a council vote.
At Derby, morale plummets when promised English and French support fails to materialize.
Historical irony: London was nearly undefended, “Had Charles and his men marched down, there probably wouldn’t have been enough time for British reinforcements to come in.” [24:20]
The retreat marks a turning point; Charles becomes increasingly despondent.

6. The Battle of Culloden and the Collapse

[25:55–28:30]

Culloden is framed as a decisive and disastrous end for the Jacobites.

“One big mistake was fighting on slow, boggy, flat ground, which allowed the British clear lines of free fire and made the Jacobite soldiers slow on their charge... By the time the Jacobites advanced, Charles almost certainly knew that it was pretty much a lost cause.” [27:09]
Notably grim detail:

“Two of Charles’s messengers did get decapitated by cannonballs one after another, which probably wasn’t great for morale.” [27:26]
Charles is convinced to abandon the field—a reluctant, emotionally impactful act.

7. Charles’s Flight and Flora MacDonald’s Role

[28:30–32:10]

The British offer a £30,000 reward for Charles, making trust a scarce commodity.
Flora MacDonald, from a Protestant family and engaged to a British official, agrees to help Charles, disguised as her maid "Betty Burke."

“She said she helped Charles because he was a human being in need. Years later, she would tell Frederick, the Prince of Wales, that she would have done the same for him.” [30:02]
Tense escapes, including a dangerous brush with military officers in Lady Margaret Macdonald’s home, highlight Flora’s extraordinary composure.
After parting at Portree, Charles continues his flight, including further escapes in disguise and near-fatal mishaps.

8. The Legacy of Flora MacDonald and Romanticization

[32:10–36:45]

Flora is briefly imprisoned but quickly becomes a celebrated figure in England—her bravery co-opted into romantic Scottish folklore.

“By the Victorian era, Flora MacDonald as a figure became woven into a romanticized ideal of Scotland, along with Mary, Queen of Scots and the Bonnie Prince Charlie himself. She was a piece of folklore by that point, almost.” [34:25]
Dana’s incisive commentary on the ways conquered histories get sanitized:

“For the English it’s easier to romanticize the rebels who rose up against them when those figures are safely in the past, posing no real threat to their status quo.” [34:40]

Notable Quotes & Memorable Moments

On Flora’s motivations:

“She said she helped Charles because he was a human being in need. Years later, she would tell Frederick, the Prince of Wales, that she would have done the same for him.” (Dana Schwartz, 30:02)
On romanticizing history:

“An Englishman could read a book or poem about Flora MacDonald, pat himself on the back for appreciating how stirring her small moment of history was in beautiful windswept Scotland, and then continue on enjoying the cultural hegemony of England.” (Dana Schwartz, 34:52)
On what might have been:

“If Charles and his men had done what Charles had wanted and they had pressed ahead, would they have been able to take London? It’s extremely plausible, but of course, they didn’t have that intelligence at the time to know how undefended London was.” (Dana Schwartz, 24:25)

Timeline of Important Segments

[02:05–05:25] – The origins, lyrics, and cultural weight of the Sky Boat Song
[05:25–12:00] – Historical and familial backdrop: The exiled Stuarts and rise of Jacobitism
[12:00–15:40] – Charles’s upbringing, personality, and early rebellion
[15:40–21:00] – The Jacobite campaign: cultivating support and image, foiled plans with France
[21:00–25:55] – Rebellion progresses, tactical dilemmas, and a fateful retreat
[25:55–28:30] – The Battle of Culloden: tactical errors, defeat, and immediate aftermath
[28:30–32:10] – Flora MacDonald's role in Charles’s escape, their journey and near-misses
[32:10–36:45] – Flora's legacy, transformation into legend, and critique of romanticizing rebellion
[35:17–36:45] – Flora’s later life: exile, struggles in America and Canada, return to Skye

Postscript: Flora MacDonald's Life After Charles

[35:17–36:45]

After aiding Charles, Flora married Allen MacDonald, moved to North Carolina, and, during the American Revolutionary War, found herself on the British Loyalist side.
The family endured hardship: Allen was imprisoned, their property confiscated, and their attempts to resettle in Nova Scotia failed due to climate.
Ultimately, they returned to Skye, where Flora lived out her years.

“She’s buried there now, in Kilmer Cemetery, a fitting end after a lot of global travel to spend eternity in the place of which she became an indelible symbol.” (Dana Schwartz, 36:35)

Tone & Style

Summary Takeaway

For listeners of both history and "Outlander," this episode provides both context and critique, charting the gap between what was and what we choose to remember.

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Sing Me a Song of a Lad That Is Gone

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Summary

Noble Blood: "Sing Me a Song of a Lad That Is Gone"

Overview

Key Discussion Points and Insights

1. The Origins and Meaning of the "Sky Boat Song"

2. Royal Succession and the Jacobite Cause

3. Charles Stuart’s Upbringing and Character

4. Charles as a Master of Image and Aspiring Revolutionary

5. The 1745 Jacobite Rising – Progress, Failure, and Missed Opportunities

6. The Battle of Culloden and the Collapse

7. Charles’s Flight and Flora MacDonald’s Role

8. The Legacy of Flora MacDonald and Romanticization

Notable Quotes & Memorable Moments

Timeline of Important Segments

Postscript: Flora MacDonald's Life After Charles

Tone & Style

Summary Takeaway

Summary

Noble Blood: "Sing Me a Song of a Lad That Is Gone"

Overview

Key Discussion Points and Insights

1. The Origins and Meaning of the "Sky Boat Song"

2. Royal Succession and the Jacobite Cause

3. Charles Stuart’s Upbringing and Character

4. Charles as a Master of Image and Aspiring Revolutionary

5. The 1745 Jacobite Rising – Progress, Failure, and Missed Opportunities

6. The Battle of Culloden and the Collapse

7. Charles’s Flight and Flora MacDonald’s Role

8. The Legacy of Flora MacDonald and Romanticization

Notable Quotes & Memorable Moments

Timeline of Important Segments

Postscript: Flora MacDonald's Life After Charles

Tone & Style

Summary Takeaway