Valor Friday

| July 2, 2021

I’ll be digging deep into American history for this week’s amazing subject. Anne Hennis Trotter Bailey was an English woman born in Liverpool in 1742. She emigrated to the American colonies when she was 19 after losing both her parents. She settled in the Shenandoah Valley area of Virginia.

Bailey married a militia soldier, Richard Trotter, who died nine years into their marriage. Trotter was serving in the Virginia militia in Lord Dunmore’s War (1774) when he was killed in action against Shawnee forces at the Battle of Point Pleasant. This was a conflict between the Shawnee and Mingo tribes and the Virginia Colony.

The 32-year old widowed mother of a young son, Bailey was apparently quite enraged by the Shawnee killing of her husband. She left her son with a close neighbor Mrs Moses Mann and joined the militia to avenge the death of her husband.

Bailey would ride between recruiting posts and implore the settlers to join the militia to defend the colony from the Natives first and then the British. On one such trip she was accosted by a party of Shawnee. After being pursued by the warriors, she jumped off her horse and hid in a rotted log. Despite the braves sitting on that very log while they searched for her, they resigned themselves to merely taking her horse. That night, Bailey snuck into their camp and stole back her steed.

Once away from camp, Bailey began to scream and shriek. The Shawnee thought she was possessed and invulnerable to bullets or arrows. The Shawnee gave her the nom de guerre “Mad Anne” and the “White Squaw of Kanawha.”

A year later, when the American War of Independence broke out, the Virginia Militia (famous for having been George Washington’s command during the French and Indian War) was pressed into service. Over the course of the next eight and a half years, Bailey served as both a scout and a courier during the war. Dressed as a frontiersman, it’s been said that she learned to both drink and cuss like a soldier.

After the war, Bailey remained with the militia. It was in this capacity that she again went to war, this time against her most reviled enemy the Shawnee.

The Northwest Indian War was started in 1785, less than two years after the Revolutionary War ended. The Treaty of Paris, which ended that war, ceded the area of the Ohio Territory to the US. This left the Great Lakes as the natural dividing line between the US and British Canada.

In contravention of their treaty obligations, the British still had military forces manning forts in the Ohio and Illinois Countries and were providing material support to the Native tribes there, who were warring with the nascent US government and militia forces.

After a series of raids against settlers in the newly organized Northwest Territory, the new President of the United States George Washington ordered the US Army to exert sovereignty in the territory in 1790. The problem was that after the Revolutionary War, there was not intended to be any standing US Army. Therefore, the new Army was formed of mostly untrained recruits and militiamen.

After a series of stinging defeats, Washington ordered Revolutionary War hero General Anthony Wayne to organize a proper fighting force. He took command of the Legion of the United States in 1792. This force successfully prosecuted a war against the Tribes and their British backers. By 1795 the tribes were forced to cede significant territory and Britain was forced to abandon their military forts on US soil.

During this conflict Anne Bailey would marry a second time, in 1788 to John Bailey. He was also a frontiersman and a ranger for the militia. The couple was posted to Fort Lee, Virginia.

Bailey continued her military service by patrolling the area around the fort for hostile Native forces and working as a messenger between Fort Lee and the remote, forward frontier posts.

It was here at Fort Lee in 1791 when Bailey distinguished herself in battle. While under heavy attack, the defenders of Fort Lee (now Charleston, West Virginia) were running out of ammunition. Bailey volunteered to make a run on horseback, alone, 100 miles across rough terrain.

Bailey completed the difficult journey unscathed, reaching Fort Savannah in Lewisburg. After loading up with the needed supplies, she returned across the 100 miles of wilderness to relieve the besieged Fort Lee just three days later.

Bailey is credited for saving the fort with her heroic ride. Since the US had no medals or other awards and decorations at the time (they being too European), Bailey was gifted the beautiful black horse she rode on that fateful journey. He was said to have white feet and a blaze face. She named him Liverpool in honor of her place of birth. Bailey remained in service with the militia until 1795 when the Treaty of Greenville ended the conflict.

Unfortunately for Mad Anne, her second husband John died somewhere between 1794 and 1802. Twice widowed, she lived with her son. She spent her later years travelling the country, ranging as far south as Alabama. When her son moved west into Gallia County, Ohio, she joined them in 1818.

Anne was once again on the frontier, where she apparently most preferred to be. Even though she was 76, she still found work as an express rider.

In 1823, Ann Bailey was interviewed by Anne Royall, a local reporter in the Ohio area she’d settled. When speaking of her adventures and bravery she said, “I always carried an ax and auger, and I could chop as well as any man… I trusted in the Almighty… I knew I could only be killed once, and I had to die sometime.”

Mad Anne Bailey died in 1825 at the age of 83. She died in November of that year, so she lived long enough to see the country she played a role in forming pass its 50th anniversary. She was buried there, near her son’s home, but was re-interred 76 years later at Monument Park in Point Pleasant, West Virginia (in Bailey’s time, this was still part of Virginia).

Bailey’s ride was recounted nearly a century after her deeds with the poem “Anne Bailey’s Ride” from 1861.

Category: Army, Historical, Valor, We Remember

Comments (6)

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  1. Veritas Omnia Vincit says:

    Great story, and in interesting piece of history.

    The number of average people doing very un-average deeds to build this country becomes a testament to the pioneering, independent spirit of those involved.

    That’s one tough lady.

  2. KoB says:

    Just…DAAAYYUUUM!!! Yep, one hell of a tough Lady Warrior. “…could only be killed once…” And you got to give a little credit to that horse, Liverpool. Toted her, them brass ovaries, and the supplies, thru the wilderness, making a 200 mile round trip in 3 days. A Battery Gun Salute for her and the horse!

    Great story Mason…Thanks!

  3. SgtBob says:

    “An Uncommon Soldier” is a good account of Sarah Rosetta Wakeman, aka Pvt. Lyons Wakeman, 153rd NY volunteers, Aug. 30, 1862 – her death, June 19, 1864. One amazing thing is the number of people who knew what Wakeman was doing, including her family back home and two cousins who were in an Ohio infantry regiment.

  4. Roh-Dog says:

    Dang. What a beast!
    If the good Lord drags these bones by Point Pleasant, WV I’ll pay my respects.

  5. Mason says:

    Forgot to mention that, for comparison’s case, then Assistant Surgeon Leonard Wood (later major general and Chief of Staff Army) earned the Medal of Honor in 1886 for making a similar 100-mile trek through hostile Native territory.

  6. AW1Ed says:

    Another great one, Mason. Thanks.