Captain James Callaway

by Bob Brail

It is not uncommon for residents of the Boone-Duden area to know about the importance of Missouri during the Civil War. One major battle, at Wilson Run near Springfield, was fought early in the war. The status of Missouri as a slave state that had not seceded meant that there was constant strife within the state between supporters of the Union and the Confederacy. Not as many residents are aware that the eastern portion of Missouri, including the Boone-Duden area, played a role in the War of 1812. Several area men served in that war. The best known is probably Captain James Callaway, a resident of Howell Prairie, who was killed by Indians during an incident that occurred less than three weeks after the Treaty of Ghent officially ended the war.

James Callaway was born in Fayette County, Kentucky, on September 13, 1783, the firstborn son of Flanders and Jemima Boone Callaway. His mother was the daughter of Daniel Boone who had been captured by Indians in 1776 and rescued three days later by her famous father and other men. Flanders and Jemima had married in 1780 and around 1800 moved from Kentucky to Charette in present-day Warren County, about two miles from modern-day Marthasville.

James Callaway had begun his education before the family left Kentucky, so after their arrival in Missouri Territory, Callaway was sent back to Kentucky to finish his education. By 1802 he was back in Missouri Territory. He accompanied Daniel Boone, Nathan Boone, and others on two hunting trips in the fall of 1802 and again in the fall 1803, roaming through what became western Missouri and even as far as present-day eastern Kansas. In 1804 he took another trip back to Kentucky, this time with two cousins to sell furs. Callaway married eighteen year old Nancy Howell, daughter of Francisand Susannah Howell, on May 9, 1805. By the time of Callaway's death in 1815, the Callaways would have three children: Thomas (born 1806), William (1807), and Theresa (1811). Callaway and his wife built a cabin on the north side of a small creek that Callaway named Kraut Run where they farmed. The cabin was located within the boundaries of what became the August Busch Conservation Area. The Callaways' spring was still identifiable with its rock wall enclosure as late as 1922; its possible location is west of the southwest corner of Lake 33 and north-northeast of the Busch Archery Range near a small pond.

Like many of the people of his time who were descended from Daniel Boone, James Callaway was a slave owner. Although the number of slaves he owned is not known, documents pertaining to some of his slave purchases survive. The oldest document was written on April 2, 1808, when Callaway purchased for $600 a twenty-one year old slave named Moses from an individual who lived in Indiana Territory. The document not only states the sale of the slave, but also goes on to say that Callaway, and no one else, has the right “to seize and take into his possession” the slave Moses as Moses “descends the Missouri River.” One might infer from this wording that Callaway purchased a slave who then ran away before being delivered to Missouri Territory.

Callaway purchased five more slaves in the final fourteen months of his life, which suggests he was doing well financially. Callaway bought thirteen year old Isaac for $400 on January 21, 1814. In a letter to his wife in June of 1814, Callaway writes that he intends to buy a slave from a peson named Zumwalt; later that year, on December 22, Callaway paid $500 for Moses, age twenty-one, from William Hays. The next month Flanders Callaway sold three slaves to his son James Callaway for $450 dollars: Venus (Venie) and two boys, Daniel and Westly.

Besides farming, Callaway was heavily involved in community affairs and was respected by his neighbors. For a time he served as deputy sheriff of the St. Charles District of the Missouri Territory. He was also a tax collector and served in other local positions. In July, 1810, Frederick Bates, Secretary of the Missouri Territory, appointed Callaway to assist in taking the Missouri Territorial census for the St. Charles District. In 1812, Callaway was appointed to administer oaths in the St. Charles District. One family chronicler states that Callaway's “intelligence and strict integrity as a man gave him the confidence, respect, and friendship of all his neighbors.”

It is for his involvement in military affairs, however, that James Callaway is best remembered. He may have been captain of a militia company as early as 1810. In 1812 President James Madison declared war on Britain, and Missouri Territory became part of the western theater of the conflict. The British government sent agents to the area west of the Mississippi to encourage local Indian tribes to join its side against the Americans. The British supplied guns and ammunition to the Indians, who agreed to war against the Americans, burning homes, stealing and killing livestock, and even killing Americans. In response to these attacks, the local settlers formed groups of “rangers,” who protected farming families living in comparative isolation from one another. In 1812, Callaway captained a local militia and a troop of rangers, who guarded frontier settlers, and also did duty as a spy during this time. One family account states that by 1813 Callaway was a lieutenant in the company of rangers led by his uncle, Daniel Morgan Boone; when Boone resigned, Callaway received an Army commission at the rank of captain and led the company, which consisted of men from St. Charles, Lincoln, and Warren Counties. Settlers in the St. Charles district eventually built several “forts,” small fortifications where they could go when Indian attacks were likely. Callaway's rangers and others were responsible for the protection of these forts. When they were attacked, the rangers would quickly respond.

Callaway and his rangers also fought away from home. In August, 1813, Nathan Boone led a small reconnoitring force of about fifteen rangers, including James Callaway, to scout possible routes for General Benjamin Howard's march into Illinois to stop the advance of he Indian forces. On August 15, Boone's party was attacked in Illinois and forced to retreat across the Mississippi River. According to Callaway, “the Indians routed [them]. Boone's men then joined Howard's forces and, on September 17, the soldiers crossed the river into Illinois, eventually reaching Peoria. While at Peoria, James Callaway assisted in the building of Fort Clark.

In August, 1814, General Zachary Taylor led a force of over 300 men in eight keelboats up the Mississippi with the goal of capturing the fort at Prairie Du Chien. One of those keelboats was under the command of James Callaway, who had just been promoted to the rank of “Captain of Rangers in the service of the United States.” The first major obstacle standing in the way of Taylor's force was a Sauk village near present day Rock Island, Illinois. Taylor's small command faced about thirty British manning small atillery and approximately 1000 warriors led by Black Hawk in what is now known as the Battle of Credit Island. In an hour the eight keelboats were hit over fifty timesby artillery fire. During this barrage, according to a story told by his descendants, Callaway commanded his men in their keelboat, apparently unaffected by the fire directed at their boat. Callaway's men, on the other hand, were doing their best to avoid being hit, by ducking and squatting in the bottom of the boat. Callaway chastised them, saying, “Boys, what are you dodging for?” Just then a ball whizzed by Callaway, and he involuntarily moved. One of his men said, “Captain, you dodged.” Callaway then smiled and said, I could not help it.” Callaway later described the artillery as “enough to knock the splinters [of their boat] into the men's faces.” During Taylor's retreat toward St. Louis, Callway and his men covered and protected the rear of their forces.

During the retreat, Taylor and his army stopped at the present location of Warsaw, Illinois, in Hancock County, and left Callaway and a Captain Whiteside in command of several men with the order to build a small fort. Callaway was there several weeks, assisting in Fort Johnson's construction, and commanding the soldiers there. Because of a supply problem, the fort was abandoned and burned in late October.

During this time while they were separated, Callaway and his wife Nancy, back at their cabin on Howell Prairie, wrote letters to one another (since Nancy was illiterate, she must have dictated her letters). Although none of Nancy's letters survive, eighteen of Callaway's are held at The Missouri Historical Society Research Library in St. Louis. These letters were written by Callaway to his wife from May, 1813, to March 5, 1815, just two days before Callaway's death. There is also a single letter Callaway wrote to his parents in 1814. This is the only correspondance of Callaway that survives. In these letters, Callaway gives an interesting, although not surprising, picture of who he was. Without a doubt, Callaway was devoted to his wife and children, and to his extended family. Every letter, without exception, expresses his love and respect for Nancy, “a woman worthy of every blessing and calculated to render [him] entirely happy.” He frequently writes of the loneliness and difficulties and dangers experienced by Nancy as she runs a farm and raises a family without his presence. (One story passed down by the family describes the slave Venus saving Nancy and the three children from Indian attack during one of Callaway's absences.)

Every letter but one reveals a strong affection for his three children; in one Callaway directs his wife to “kiss my daughter for me and shake hands with the boys.” When his three year old daughter is sick with measles, Callaway writes of his hopes for her recovery, telling Nancy, “Let her drink warm tea, coffee, or some other warm drink night and morning and she will soon recover.” He also regularly expresses a desire for his children to receive an education. In one letter Callaway tells his wife “that as soon as they can spell well I shall give them a Copy Book and let them learn to write.” In another, he tells Nancy he wants his children to have “good learning” and to be taught “humanity and gentility.” He instructs Nancy, “Tell the boys if they go to school and learn well that I will give them a handsome present when I am done ranging.” Callaway clearly is a man who loves his family.

Callaway is, however, also a man who does his duty, even when it separates him from his family. He tells his wife, “A man in the service situated as I am is tossed and carried about like a ship on the sea without a rudder or a man to steer her; he may make calculations how and when he will go but if a storm arises he is on a contrary course. Such is the case with me.” He writes that he would like to return to his family but he finds “this frontier . . . too dangerous to be left unguarded and as it is consigned to . . . my command . . . I do not think it possible for me to leave it.” Callaway even writes that he is “almost ready to resign [his] commission” when he thinks about his wife and children “unprotected in a savage world,” and “that no man longs [more] for a private life than I do.” At one point he tells his wife, “I shall quit the woods. I am determined on it.” Callaway's belief, though, is that a “man embarking on his country['s] cause is not only honourable but his duty.”

It was his sense of duty that placed James Callaway at Fort Clemson on Loutre Island as 1814 drew to a close. In December Callaway and his rangers fought Indians in the area of present-day Troy, Missouri, and then on December 31 retreated to Fort Clemson at the mouth of the Loutre River in the southeastern corner of modern-day Montgomery County, just across the Missouri River from Hermann, to protect settlers in that area. Winter weather temporarily ended most of the fighting, but by early March Indian raids resumed, since the news of the ratification by Congress of the Treaty of Ghent, which officially ended the War of 1812, in mid-February apparently had not reach this area's combatants. In a letter to his wife dated March 5, 1815, Callaway wrote of Indian activity near Loutre Island which caused Callaway and several men to ride out in the middle of the night to save the Jacob Quick family. On March 6, Callaway sent about fifty rangers, about half of his men, to patrol in the area of modern-day Montgomery City.

That night Sac, Fox, and Pottawatomie Indians (estimates range from thirty to one hundred) stole several horses from Fort Clemson and retreated north. On the next morning, March 7, Callaway led Lt. David Bailey, Lt. Jonathan Riggs, and seventeen men other men (Privates James McMullin, Hiram Scott, Frank McDermid, William Keithley, Thomas Bowman, Robert Baldridge, James Kennedy, Thomas Chambers, Jacob Groom, Parker Hutchings, Mr. Wolf, Thomas Gilmore, John Baldridge, Joshua Deason, James Murdock, William Kent, and John K. Berry) in pursuit of the Indians up the west bank of Loutre Creek in the western half of what is now Montgomery County. At about noon Callaways party crossed the Prairie Fork branch where it emptied into Loutre Creek, a few miles south-southwest of modern-day Mineola. Around 2 :00 PM, about ten miles further to the north, they found the stolen horses guarded by only a few Indian women, who fled upon the arrival of Callaway and his rangers. The horses were easily recovered. After a thorough search of the immediate area, no evidence of the Indian raiding party could be found. The trail had “disappeared as if the party had scattered.”

Because of behavior of Indian women, Lt. Jonathan Riggs, a very experienced officer, was nervous about an ambush, believing that the Indians had scattered to reform and attack when not expected on the return to Fort Clemson. Riggs specifically feared the crossing of the Prairie Fork branch, which he said was “peculiarly favorable for an ambuscade.” So Riggs advised James Callaway to return to Fort Clemson by a different route.

According to all versions of the incident, Callaway disagreed, thinking that the Indians had gone on to the north to their main camp. He told Riggs he thought there were few Indians in the area, so he decided to return the way they had come. In his A History of the Pioneer Families of Missouri, published in 1875,William Bryan stresses that many of Calllaway's relatives were still living who were interviewed for the book, including Callaway's sister, Susannah Howell, and at least two of Callaway's rangers, William Keithley and Rev. Thomas Bowen, although they were not with Callaway on March 7. Though Bryan depends on Callway's relatives and former rangers for his information, Bryan's version is critical of his actions: “Captain Callaway was an experienced Indian fighter, and as wary as he was brave, . . . on this occasion he did not allow himself to be governed by his bettr judgment.” Another chronicler of that day wrote that while “Captain Callaway was, perhaps, better suited to command where desperate fighting was to be done and regardless of consequences, Lieutenant Riggs was unquestionably his superior as a general officer to plan movements, calculate results and conduct successful operations.” At Callaway's command, the party turned back to Fort Clemson with the recovered horses.

One mile north of the Prairie Fork branch, Callaway stopped his men so they could eat and the horses rest. Once again Lieutenant Riggs warned Callaway of an ambush. William Bryan writes that Callaway “flew into a passion and cursed [Riggs] for a coward.” He told Riggs he would return the way he had come even if he had to go by himself. Riggs “reluctantly followed his Captain.”

The ambush occurred where Riggs feared, just to the west of where the Prairie Fork branch meets Loutre Creek, near Mineola. On their return, Callaway's force reached Prairie Fork about seventy-five yards from Loutre Creek, in Township 47 North Range 6, at the boundary of Sections 15 and 16. McMullin, MacDermid, and Hutchings were at the front of the party, leading the stolen horses. They crossed the Prairie Fork branch first, near its confluence with Loutre Creek. When they reached the south bank, the Indians opened fire and immediately killed all three men and all the stolen horses. At this time, James Callaway was riding about 150 feet behind the three men and the horses. He raced toward the gunfire. As he neared the branch, Callaway veered off toward the left toward Loutre Creek. When he entered the water, his horse was shot dead through the head. Callaway was also hit by a ball in his left breast pocket, but the ball hit Callaway's watch which shattered, momentarily saving Callaway's life. One account states he was also wounded in his left arm during this volley. Callaway fell from his horse, losing his gun in the water. At this point Callaway began swimming down the branch toward Loutre Creek, but he was shot in the back of the head, the ball lodging in his forehead. Callaway died instantly. “His disregard of danger was so great that it amounted to a fault” is the conclusion of one historian who wrote about the death of Callaway.

The remainder of men led by Lieutenants Riggs and Bailey reach the stream and exchanged fire with Indians. Outnumbered by as much as eight to one, Riggs ordered a retreat south toward the safety of Fort Clemson. As the fight continued during the retreat, Hiram Scott and Mr. Wolf somehow became separated from the others. Scott was killed, but Wolf survived and was the first of Callaway's party to arrive back at Fort Clemson. Wolf mistakenly thought he was the only soldier who had survived, reporting that all the other men had been killed by the Indians. Riggs and Bailey finally reached Fort Clemson after dark.

The next day Riggs returned to the site of the ambush with fifty men. They found the mutiliated bodies of McMullin, McDermid, and Hutchings cut into pieces and hung in bushes. Riggs and his men removed the corpses and buried them about 100 yards south of the Prairie Fork branch, covering the grave with rocks. According to some accounts, Riggs' party could not initially find Callaway's body. It was finally found about 200 yards downstream in a willow thicket on the south bank. The body was removed up a slight hill on the south bank, wrapped in blankets, and buried there.

When word of her husband's killing reach Nancy Callaway, she was attending a school run by Prospect Robbins near her home on Howell Prairie, “trying to remove that handicap”of illiteracy. When she heard the devasting news, Nancy Callaway did not utter a word as she put on her sunbonnet and left. She walked home and fainted when she reached the house.

Other accounts have Callaway's body being found when his father, Flanders Callaway, led a group of men to the site days later. These accounts state the body was found by Benjamin Howell when Flanders Callaway went to the site and he was there when his sons body found. One account maintains that Daniel Boone and his son Nathan were in the group. In June Flanders Callaway, and several of James Callaway's former rangers visited his grave, lined and covered it with rocks, and placed a large rock at the head of grave. On the rock were carved these words: “Capt. Jas. Callaway, March the 7, 1815.” Callaway's grave and those of his three rangers are located on what is now private property in Montgomery County near Mineola.

In this modern day and age, it has grown increasingly controversial to classify an American who owned slaves and fought against Native Americans as someone to be admired. In the case of James Callaway, perhaps it is sufficient to state that the man was a product of his times concerning his attitudes about race, but that his devotion to family and duty were worthy attributes. James Callaway is one of the many men from this area who fought on behalf of the United States in the War of 1812, and he should be remembered.

Sources: “Battle of Rock Island Rapids” (en.wikipedia.org); Callaway Family by Martha Callaway Winkler, 1978 (occgs.com); “The Callaway Family” by W. H. Burnham, Register of the Kentucky State Historical Society (jstor.org); “Capt. James Callaway's First Company of Rangers” by Andrea Myers (genealogytrails.com); Crow's Nest by Lilian Hays Oliver; Federal Censuses; Findagrave.com; A History of the Pioneer Families of Missouri by William Bryan (archive.org); History of St. Charles, Montgomery, and Warren Counties (archive.org); “Indians Kill Captain Callaway,” Pioneer Montgomery (montgomery.mogenweb.org); “James Callaway in the War of 1812,” Missouri Historical Society Collection, Vol. V No. 1, October 1927, by Edgar B. Wesley; “James Callaway Papers, 1792-1854,” Missouri Historical Society (Identifier A0970); My Father, Daniel Boone, the Draper Interviews With Nathan Boone, edited by Neal O. Hammon; Some Boone Descendants and Kindred of the St. Charles District by Lilian Hays Oliver; Standard Atlas of Montgomery County, Missouri, 1897 (digital.shsmo.org/digital); This Week in Missouri History, Missouri Historical Society, March 1930 (wikitree.com).