Legends of the Old West – FRONTIERSMEN Ep. 2 | Daniel Boone: “Battle For Boonesborough”

Host: Chris Wimmer, Black Barrel Media
Date: October 1, 2025

Episode Overview

This episode chronicles the perilous and pivotal years of Daniel Boone’s efforts to establish American settlements in Kentucky—especially the defense and survival of Boonesborough. It explores the escalating frontier violence, Boone’s leadership through brutal conflicts with Native American nations, the reverberations of larger colonial wars, and the seeds of legend, all during the tumultuous build-up to the American Revolution.

Key Discussion Points and Insights

1. Frontier Violence and the Genesis of Lord Dunmore’s War

• Shawnee Attacks & Colonial Response (00:41):

  • By 1774, Daniel Boone’s life on the frontier was marked by constant threat: “Ambushes, massacres, and mutilations by Shawnee warriors and their allies occurred up and down the Appalachian mountain range.”
  • Boone had earlier survived Shawnee captivity and lost his son James in an attack during an aborted settlement attempt in Kentucky.

• Yellow Creek Massacre (03:20):

  • Colonial men, acting on rumors, killed a group of Mingo at Baker’s Tavern. When more Mingo arrived by canoe, most were shot and killed.
  • “Regardless of the details, the attack became known as the Yellow Creek Massacre.” (06:30)
  • The Mingo and Shawnee retaliated, marking the start of Lord Dunmore’s War.

2. Boone’s Frontier Missions and Rising Leadership

• Warning Surveyors (08:30):

  • With war breaking out, Boone and Michael Stoner trekked over 800 miles into Shawnee territory to warn land surveyors, discovering both survivors and the mutilated bodies of the unlucky.

• Militia Promotion (09:40):

  • Boone, for his heroics, was made a militia captain, defending outposts like Fort Blackmore and Fort Cowan.

• Battle of Point Pleasant (10:00):

  • Colonial victory pushes Shawnee Chief Cornstalk to the negotiating table, ending Lord Dunmore’s War and clearing the path for new settlements.

3. Founding of Boonesborough and Renewed Conflict

• The Wilderness Road & Boonesborough Founded (12:40):

  • Sponsored by Richard Henderson, Boone blazes the "Wilderness Road" into Kentucky, enduring fresh Shawnee ambushes that cost the lives of an enslaved man, Sam, and his owner.
  • “Boone's Trace...became the first major route for Americans to venture westward into Kentucky.”
  • Boonesborough is established as a fortified settlement and quickly joined by two neighboring communities.

• Rising Revolutionary Sentiment (14:20):

  • As the American Revolution breaks out, both the Shawnee and Cherokee ally with the British, aiming to reclaim lost lands by ousting settlers.

4. The Kidnapping of Jemima Boone and Heroic Rescue

• The Abduction (17:30):

  • Boone’s daughter, Jemima, and two Callaway girls are abducted on July 14, 1776 by a mixed party of Shawnee and Cherokee warriors.
  • The girls leave signs and drag their feet to mark their trail, actively resisting.

• Boone’s Pursuit and Rescue (18:50):

  • Boone and a small group track the captors for days, then make a daring rescue at a river crossing.
  • Boone’s opening shot signals the attack, with Jemima yelling, “That’s Daddy!” (21:53)
  • Boone shouts to prevent a friendly fire incident:
    • “For God’s sake, don’t kill her when we have traveled so far to save her.” (22:55)

• Legacy:

  • This real-life event inspired James Fenimore Cooper’s novel, “The Last of the Mohicans,” and later popular films.

5. Expanding War and “The Bloody Sevens”

• British Policy Shift (24:40):
  • The British begin actively enlisting Native American nations to attack rebel settlements. The period is remembered as the “Bloody Sevens” for the wave of raids and massacres that follow.
  • A frontier leader’s plea: “We are surrounded with enemies on every side and our fort is filled with widows and orphans.” (27:00)
  • Ironically, some Loyalists also fall victim, shifting more sympathy toward the Patriots.

6. The First Siege of Boonesborough

• Near-Overrun Defended by Outnumbered Settlers (28:00):
  • March–April 1777: Chief Blackfish leads 70+ warriors in attacks—the dead are mutilated, syrup is drunk, tensions boil over.
  • Daniel Boone and Simon Kenton, with only 14 men, fend off over 100 Shawnee in a surprise attack. Boone is shot in the leg and nearly tomahawked, but is saved by Kenton:
    • “We are gone, but let us sell our lives as dearly as we can.” – Boone, rallying his men (29:12)
    • Kenton kills four warriors and hauls Boone back to safety under fire. Boone’s family tend to his injuries, but he refuses to rest, instead helping strengthen the fort and intelligence networks.

7. The Oncoming Storm: 1777 Siege

• Mounting Pressure and Defensive Innovations (32:10):
  • Boone trains men to guard while others farm, instructing to look for “the glint of sunlight off of gun barrels.”
  • Ammunition is conserved for real threats—“The Shawnee were too smooth to give themselves away by moving recklessly.”
  • May 23, 1777: Over 200 Shawnee warriors approach—the episode ends with Boonesborough on the brink of a renewed siege.

Notable Quotes & Memorable Moments

• On the madness of frontier warfare:
  “Ambushes, massacres, and mutilations by Shawnee warriors and their allies occurred up and down the Appalachian mountain range.” (00:41)
• Boone’s tactical foresight in the rescue:
  “For God’s sake, don’t kill her when we have traveled so far to save her.” – Daniel Boone, averting tragedy during the rescue (22:55)
• Describing the defensive spirit:
  “We are gone, but let us sell our lives as dearly as we can.” – Boone, before a desperate charge (29:12)
• Summing up the fragility of the settlements:
  “Our fort is filled with widows and orphans.” – Kentucky settler (27:00)

Important Timestamps

• 02:10–06:30: Yellow Creek Massacre and Lord Dunmore’s War begins
• 08:30–10:00: Boone’s perilous mission to warn surveyors
• 12:40–14:20: Founding Boonesborough and the Wilderness Road
• 17:30–23:10: Kidnapping of Jemima Boone and the dramatic rescue
• 24:40–27:30: “Bloody Sevens” – British-Native strategy and settler suffering
• 28:00–32:10: First siege and defense of Boonesborough
• 32:10–35:50: Preparations for another siege; episode cliffhanger

Summary

This gripping episode brings to life the violence, courage, and shifting alliances of the Kentucky frontier during Daniel Boone’s most legendary years. Listeners are shown Boone’s relentless bravery under impossible odds, the trauma and terror wrought by a volatile, multi-sided struggle for land, and the roots of American and pop culture myth. The episode ends on the precipice of one of the most significant sieges of Boonesborough, with a promise of escalating drama, betrayal, and resilience to come.

Next Episode Preview:
Boone faces even more harrowing dangers: “He gets captured and nearly killed by the Shawnee. He faces a shocking court martial for treason.” (35:50)

Production Credits:
Written and researched by Michael Meglish, produced by Joe Garop, original music by Rob Valier, hosted by Chris Wimmer.