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The Once and Future C&F - Captain Whiley’s Enterprise
L ike a lot of us, Richard Whiley’s path into the insurance business was not a straight line. He was born in London in 1767 and came to the U.S. in the 1780s — and then things got interesting. The first permanent settlement in Ohio (which was considered “the Northwest” back then) was established in 1781 1 . There was a lot of friction between the settlers and the Indigenous Americans. The US Army at the time was small, but they sent 2,000 soldiers to Ohio to protect the settlers. In 1790, the army was defeated by the locals — with support from the British and Canadians — near what would later become Fort Wayne, Indiana (named after Anthony Wayne). In response, the US government rushed to undertake a second military expedition. They also got their hats handed to them. President Washington and Congress were not interested in losing another conflict, so they thought hard about who to put in charge. They picked one of the few remaining Revolutionary War leaders capable of service — affectionately known as “Mad Anthony” Wayne. General Wayne agreed to take the command, but stipulated that he would not go into action until his soldiers were trained and ready. A description of the recruits (many of whom deserted on the way to the Pittsburgh training camp) is very unflattering — not quite “The Dirty Dozen” but implying that they were mainly otherwise headed to jail. By early 1793, Wayne had transformed his rag-tag recruits into a disciplined army in “Band of Brothers” fashion (if you want, you could now mentally picture a frontier training montage). Richard Whiley was an enlisted dragoon (horse-mounted infantry) in General Wayne’s army. This “Legion of the US” moved into position to protect the settlers, but then waited as Congress was negotiating with the tribal leaders to see if they could find a peaceful outcome. In the meantime, Wayne — an engineer by training — put his troops to work building Fort
Recovery. In the spring of 1794, the Legion was joined by volunteer mounted riflemen from Kentucky (including William Clark of Lewis and Clark fame, who wrote an account of his time on this campaign). In the summer, the tribes gathered to attack the fort and were fended off. About a month later, the army moved into action. In 11 days, they marched 76 miles in a careful and disciplined fashion through dense forest. They constructed a 210-foot bridge across a swamp. They built another base of operations and named it Fort Defiance. Shortly thereafter, the army found the amassed Indigenous forces encamped in thick woods near a British fort. Wayne sent a messenger with a final peace offering, which was rejected. The Battle of Fallen Timbers only lasted 40 minutes, but essentially ended the 10-year Northwest Indian War, driving the British out of the Northwest and laying the foundation for America’s western expansion. It sounds like a rough way to live. The army was underfunded, so the soldiers were living in the woods for years with limited food and clothing, building lodging as they went — all under the constant threat of attack. Even so, military life seemed to agree with Richard Whiley, who in 1796 was appointed a lieutenant in the Artillerists and Engineers and followed Major Henry Burbeck to Fort Mackinac. A few years later, Whiley was put in charge of a reduced force at Fort Mackinac. Around this time, British Lieutenant George Landmann described Whiley as “a young, fair, beardless personage, on good terms with himself and placed great reliance for his military dignity on the length of his boots and the thickness of his queue” — which sounds a little judgmental - but does tend to match the only picture we have of Whiley.
1. For some of the details of this chapter, I have relied on history books. These sources, and others, are cited in the appendix.
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