Col. Richard Gentry & Boone County Soldiers in the Seminole War -- 1837

Submitted by Mary Helen Catlett Allen

Transcriber’s Note: The following appeared in the October 15th and 16th, 1937 issues of the Columbia (Missouri) Daily Tribune. It was written by William R. Gentry, Jr. St., Louis, Mo., great-grandson of Col. Richard Gentry.


On October 15, 1837, one hundred years ago today, there was great excitement in Columbia; people flocked into town from miles around to witness the departure of the First Regiment of Volunteers for the Seminole War.

The Seminole Indians had been causing trouble to the government for a long time. They had allied themselves with the British against us during the Revolution, and again in the War of 1812. They were a constant menace to the settlers of Florida and Georgia and frequently made raids on the villages of the whites, burning their crops and killing their cattle. Congress, in 1832, decreed that all Indians east of the Mississippi should be moved to the Indian Territory, and the regular army was sent to Florida, to transport the Seminoles. But the Indians took refuge in the Everglades and swamps, and could not be caught by the regulars.

By 1837, the government had spent over twelve million dollars and had almost one-half of the regular army on duty in Florida, with no results. Senator Thomas H. Benton of Missouri took a leading part in criticizing the administration of President Van Buren and declared that the job was one for western frontiersmen, rather than for the regular army. He secured the passage of legislation authorizing the raising of volunteers from the western states, and at his suggestion, Secretary of War Poinsett, commissioned Richard Gentry, of Columbia, as colonel, and directed Gentry to raise a regiment of 600 men for duty in Florida.

Gentry was a native of Kentucky. After service in the War of 1812 with Kentucky troops, he moved to Missouri in 1816, and became one of the founders of Columbia in 1820. He had been a major general in charge of Missouri troops during the Black Hawk War of 1832, and at the time of being commissioned as colonel of volunteers, he was serving as postmaster of Columbia. He was a robust, virile man, and always ready to engage in anything that promised excitement. He was a warm personal friend of Senator Benton.
His commission was issued on Sept. 8; he immediately traveled through the central portion of the state, seeking recruits. Companies were raised as follows: Boone county, Capt. John Ellis and Thomas D. Grant: Callaway county, Capt. Wm. H. Russell: Howard county, Capt. Congreve Jackson: Chariton county, Capt. James Flore: Ray county, Capt. Pollard: Jackson county, Capt. James Chiles: Marion county, Capt. John Curd.

While there were almost two hundred enlisted men in the two companies from Boone county, the records now available give only the following names:
Joseph Anthony, John R. Bennett, John N. Belcher, William H.(?) Belcher, Fred Biddle, William (?) Broaddus, G. S. Branham, James W. Brooks, Thomas U. Bryan, Edward Carpenter, Robert Carter, R. H. Coleman, R. S. Coleman, Sanford Connelly, Stephen Davenport, Sidney Farden, Morgan Funk, R. Harrison Gentry, William Gordon. David Grindstaff, Jephthah Haden, Clifton R. Harris, John M. Harris, Harrison Hawkins, Elijah Hawkins, Joseph Hickam, James G. Hopper, John Hopper, Littlebury Hunt, Thomas Jefferson, James Jones, Oliver F. Jones, Alfred Keene, John H. Kirtley, Calvin Little, William Little, Hiram Logan, William Maginess. Jacob C. March, William Martin, Samuel McCallen, Peter Mil-Holland, Joseph Morton, John Neely, Samuel Nelson, Thomas Nichols, William D. Smith, Henry Soflin, John Speake, Charles Stephens, Charles Stephenson, Jabez M. Tipton, Larkin D. Tipton, James Turner, Sam Varvell, Isaac N. Wilcoxen, Samuel Young.

A group of students and former students of the Columbia Female Academy worked long hours in making a silk flag. They took it to the office of the Columbia Patriot where this inscription was carefully printed on it:

FIRST REGIMENT OF MISSOURI VOLUNTEERS

Gird, gird for the conflict,

Our banner wave high!

For our country, we live,

For our country we’ll die!

This flag was presented to Col. Gentry’s widow after the return of the troops from Florida and is now in a glass case at the state museum in Jefferson City.

The regiment was to be mounted and the regulations called for recruits to furnish their own horses. They were to receive $8.00 dollars per month pay, plus an allowance of 40c a day for the use of the horses, all to be paid in coin. Many of the young men of Boone county wanted to go, but they did not have horses, nor the money with which to buy them. They appealed to Col. Gentry, who was in comfortable circumstances, considering the time and place, and he told them to go ahead and buy horses, giving their notes for security and that he would endorse them as additional security. Most of the notes were executed on Oct. 14, 1837, and were made payable on May 14 following which gave only seven months for the regiment to get to Florida, win the war, and get back to Columbia before the notes fell due. Col. Gentry did not realize that he would be dead and buried by that time, and that the notes would be paid by his estate, leaving nothing for his widow and nine children.

Early in the morning of October 15, the regiment was drawn up in front of Gentry’s Tavern, at the northeast corner of Broadway and Ninth street. Miss Lucy Wales, the preceptress of the academy presented the flags to the regiment. Her students were there in full force, attired in red, white and blue dresses. Col. Gentry detailed a young bachelor officer to make the speech of acceptance, but this young man was overcome with stage fright and could say nothing beyond, “Ladies and gentlemen.” The fifes and drums formed up in front, the command “Forward, March” was given and the regiment marched away. At the last moment, little Thomas Benton Gentry, the seven-year-old son of the colonel, climbed up on his daddy’s horse and rode with him to Hinkson creek. There the son told his father goodbye, and never saw him again.

The regiment made good time to St. Louis, taking only five days for the trip. They were stationed at Jefferson Barracks, south of the city, for a few days, while waiting for Senator Benton to come from Washington to address them. After his speech, they boarded steamboats for New Orleans, which they reached in six days, but they found that the city was paralyzed with an epidemic of yellow fever. People were dying faster than they could be buried, and everybody was terrified.
The regiment had to wait a few days for sailing ships. This waiting was apparently hard on the nerves of the men, who just a month before had been following a plow. They left Columbia 600 strong, but numbered 432 at the time they left New Orleans. Some of the boys apparently decided they had better get on back home while the getting was good.

Most of the men sailed for Tampa Bay on November 3, and had an uneventful trip, reaching their destination in five days. The horses were loaded on smaller ships a few days later. The loading was done by boys who had never seen an ocean, and who had no idea of how a small ship can pitch and toss in the waves, and so the horses were simply driven on board, and were not tightly packed or firmly tied. A fearful storm came up on the Gulf of Mexico on the first day out; the rolling of the ships caused frightful injuries to the horses and many were crushed to death. The storm raged so that it took three weeks to make Tampa. By that time, many more of the horses had starved. Out of the 450 horses shipped from New Orleans, only 150 arrived at Tampa in serviceable condition, and so the army authorities ordered the discharge of all men whose horses had died.

These men were paid off at Tampa, and left to get home the best way they could. Instead of paying them the agreed rates in coin, their horse allowance was cut in half, and they were paid in “shinplasters” which were nowhere near their face value. By the time this money was converted into notes on the Bank of Missouri, the men had lost heavily, and arrived home broke and thoroughly disgusted with the treatment they had received at the hands of the regulars.

The remnants of the regiment still under the command of Col. Gentry, was placed in a brigade composed of the First, Fourth and Sixth Infantry of the regular army, with Colonel Zachary Taylor in command over all. Taylor later became president, after the Mexican War. He had very little time or sympathy for the volunteers, he resented their presence, and felt insulted that they had been attached to his command.
The brigade left Tampa on December 2, for the interior. Their total strength was about 1,000, or just the size of one of our battalions during the World War. The volunteers were given the hardest job of all, that of advance guard. Throughout the whole march, they had to keep ahead of and protect the main body, and build roads to permit the passage of the heavy baggage. For over three weeks, they were kept on duty without relief of any sort.

After a march of about 150 miles through the swamps and Everglades, the brigade reached the neighborhood of Lake Okeechobee on Christmas Day of 1837. There they discovered a large body of Seminole Indians who had taken station on a “hammock,” or slight elevation of the lake. An oval-shaped swamp separated them from the brigade, but it was possible to get around this swamp on either side.
Col. Taylor called for a conference of all officers, to decide upon the best plan of attack. Col. Gentry said he favored going around the swamp, which was deep and about three quarters of a mile across. He said that the men were all near exhaustion from their travels through the mud and if they had to contend with the swamp just before the attack, he feared they would be too tired to fight a superior force. This was a wise suggestion, in view of all the facts, but it did not meet with Taylor’s approval, because it had been put forward by an officer of the volunteers. Taylor said, “Colonel Gentry, are you AFRAID to attack their center?” Gentry replied, mad clear through, “No sir. If that is your order, it will be done that way.”

And that was the order and it was done that way, and Gentry died that night, a perfect example of a subordinate sacrificed at the whim of a superior.
(Concluded Tomorrow)

The Volunteers were ordered to lead the way through the swamp, spread out in one thin line, each man about two or three yards from his neighbor. They were followed by the 6th infantry, whose men were marching shoulder to shoulder. After the 6th, came the 4th Infantry, in similar formation. The 1st Infantry, Taylor”s regiment, came last of all. It is not clear as to where Taylor was during the night; he does not say anything about it in his report, and no volunteer saw him until the fight was over that evening.

The volunteers were told to march forward through the swamp and bring on the fight. If they became hard pressed, they were to fall back in rear of the regulars and support them. They went forward at 12:20 p.m., with Col. Gentry out in front of their center. Their total strength was 132. It was hard going; the men were in mud and water up to their waists, and had to hold their guns and powder containers overhead to keep them dry.

When they reached a point about 50 yards from the edge of trees in the hammock, the Indians cut loose with a volley. Gentry was shot in the chest; many volunteers particularly on the left of the line, were also hit. The 6th Infantry, following behind in close formation, had severe losses. Gentry ran over to the left side of his line to encourage the Volunteers. “Come on, boys”, he shouted, “we’re almost there; charge on into the hammock!” Just then, the Indians fired another volley from behind the trees, and shot Gentry through the abdomen. He fell right at the edge of the swamp and the firm ground, and some Indians rushed out to scalp him. A few volunteers hurried forward to protect him, and a brisk fight ensued, during which Harrison, the Colonel’s son, was severely wounded.

The 6th Infantry began firing at this point from behind the Volunteers. This was quite disconcerting to some of the latter, who retired in some confusion. Nothing is harder for green troops than to be fired on by their own supporters, and the few who made for the rear had ample reason. But the great majority of the Volunteers threw themselves face down into the mud, and loaded and fired in that position, while the 6th Infantry worked itself up onto a line with them. There they both stayed for over an hour, unable to advance any further because of the not fire that the Indians poured into them from their hiding places in the moss of the trees.
Finally the 4th and 1st Infantry worked their way around the north side of the swamp, reached the dry ground and began to fire into this right flank of the Indians. Then the Indians retired, taking most of their dead with them and the fight was soon over.

The casualties were severe, a total of 27 killed and 143 wounded in the whole brigade, which had only about 700 men in it that morning. The Volunteers had a 25 per cent loss, being exceeded only by the 6th Infantry, which lost most of its men while they were so closely bunched up. The dead and wounded were carried back across the swamp, and the surgeons did what they could.

Col. Gentry was still alive in spite of two ghastly wounds. The surgeons decided that his abdominal would needed “cleansing” and so they put a silk handkerchief on a ramrod and pushed the whole apparatus through his belly from front to rear. This did not improve his condition to speak of; on the contrary, he began to sink rapidly. He knew that his time was limited, and he felt that Col. Taylor would belittle the actions of the Volunteers in his official report if given half a chance. So Gentry sent for Taylor, and this conversation took place.

Gentry: Colonel Taylor, I am about to die. I depend on you to do my brave men full justice in your official report.
Taylor: Colonel Gentry, you have fought bravely; you and your men have done your duty and more, too! I shall do them full justice, you may be sure.

With giving of this pledge, Col. Gentry had to be content and so he died just before midnight on Christmas Day, 1837. He was buried the following morning with the others who had been killed, and the survivors made their weary way back to Tampa.

When Col. Taylor got around to making out his report of the battle, he consulted with all of his officers of the regulars, but he did not talk to a single officer of the volunteers. In his report, he complimented Col. Gentry by saying “Col. Gentry died a few hours after the battle, much regretted by the army, and will be doubtless by all who knew him, as his state did not contain a braver man or a better citizen”. Then he went on to praise the regulars and criticize the volunteers, stating that the latter had broken and retired clear back to the baggage dump, where they refused to reenter the fight.

The report created a storm of opposition when its contents became known. Senator Benton demanded a congressional investigation; Secretary of War Poinsett hastened to disclaim any intention of slandering the action of the volunteers saying, “the heavy loss they sustained in killed and wounded affords sufficient proof of the firmness with which they advanced upon an enemy under a galling fire.” Even Col. Taylor contradicted himself when he discharged the volunteers from further service in February of 1838. He complimented them in glowing terms for the “prompt, cheerful, soldierly manner they have discharged all of the duties required of them.” He expressed pleasure at having had them under his command, wished them a safe and speedy trip home and happy reunion with their families.

But the volunteers were still mad at the treatment under his hands. When they got back to Missouri in March, they kept talking about their wrongs, and when the general assembly met in November of 1838, one of the first orders of business was a joint committee of both houses, with power to make a full investigation. The committee subpoenaed the survivors of the campaign, interrogated then closely, and found that Taylor had deliberately made a false and slanderous report of the actions of the volunteers. They declared that Taylor was not fit to hold a commission in the army, and requested Governor Boggs to lodge an official complaint with the president.

The legislature then named Gentry county in honor of Col. Gentry. But his widow and nine children were having a hard time. All of his estate had gone to meet the notes given for the purchase of horses. Senator Benton came to their assistance by having his widow made postmistress of Columbia, where she served until 1868 under ten presidents, including Zachary Taylor.

Col. Gentry’s body was brought from Florida to Jefferson Barracks in 1839. His bones were mixed with the bones of three officers of the regular army, and all were buried in the same grave. Although his widow had been promised that a suitable monument would be erected, and the names of all four officers placed thereon, the authorities chiseled on the names only of the three regulars and left Gentry’s name off.
This was not discovered until 1889 by his family, who at once requested the war department to rectify the mistake. This the department refused to do, on the grounds that no funds were available. Finally, they reluctantly permitted Gentry’s family to erect a separate stone at its own expense, but this stone could not be closer than three feet to the one already there. But now a new stone has recently been erected, and at last all four occupants of the grave are properly identified.
WILLIAM R. GENTRY, JR.