An Excerpt from Reckless: The Life and Death of Richard Gentry

From the collection of the Boone County Historical Society.  The complete 89-page book by Douglas Hunt is available from Amazon.com. 


Born in 1788, Richard Gentry has as good a claim as anyone to being the founder of Columbia, Missouri. He was part of the syndicate that bought the land on which the city was built, and he served as its first mayor. His adventurous and sometimes violent life ended on Christmas day in 1837, while he was leading an infantry charge against a band of Seminole warriors. The excerpt below, however, deals with one of the quieter battles in his life.

An Excerpt from Reckless: The Life and Death of Richard Gentry
copyright 2010 by Douglas Hunt

5 - A Saved Man

THE TWO great nemeses of Richard Gentry's life, General James Winchester and Henry Carroll,  had come from the East. In 1827 a third arrived, a Harvard-educated Presbyterian missionary named William Cochran. After a hard ride from St. Louis, sometimes into the teeth of a driving snow, sometimes through drifts that covered the trail, Cochran reached Columbia about sunset on December 3. He found shelter for himself and his horse in a tavern at the edge of town.
     A century later North Todd Gentry would say that Rev. Cochran's stop was at Gentry's Tavern, where the Colonel offered him free lodging with a strict condition attached. "Parson, this is to be your room as long as you are in Columbia, and you can do all the praying in this room that you want to, but we don't do any praying in the rest of this house." The story isn't accurate, however. By Cochran's own account, Richard Gentry had such a "peculiar hatred" of Presbyterianism that he avoided talking to the minister for three years.
For the first year, Cochran lived in Franklin, his assigned post, traveling to Columbia frequently to preach and proselytize. During these years, however, Franklin was being gradually swallowed by the changing current of the Missouri River. Late in 1828, Cochran moved to Columbia permanently, preaching two Sundays each month to country congregations and two Sundays in town. The results were disheartening. Presbyterians trickled into the Columbia meeting from time to time. A few became members on paper before they trickled out again.
     North of Columbia, on the bank of Bear Creek, another church was much more successful. It had nearly 200 members, three ministers, and a building of its own. This was the home of the New Lights, Cochran's antagonists. Historically, the New Lights were Presbyterians who had thrown off the restraints of church doctrine and discipline in favor of born-again enthusiasm. They ridiculed Cochran as a "larnt" and "hired" clergyman, manifestly insincere. Hostile to the idea of predestination, they accused all Old School Presbyterians of consigning infants "not a span long" to the flames of hell.
     In his uneven competition with the New Lights, Rev. Cochran held one advantage. His wife Eliza was a friend of Ann Hawkins Gentry, who sometimes attended services, not with her husband, but with her sister Sophia Hawkins Gordon. Cochran's sermons began to draw other women. Or perhaps women began to draw other women. "At length," Rev. Cochran wrote in his memoir, "there were five ladies added at the communion, the wives of five of the most prominent men of the place."
     Ann Hawkins Gentry especially interested Cochran. She had been raised Presbyterian. She knew the Shorter Catechism by heart and was committed to its teachings. Everyone in town was impressed by her. Her home, though a tavern, was a model of efficient housekeeping. Her husband, Colonel Gentry, was a force to be reckoned with. "A popular man and state senator …a man of more than ordinary talents, a good talker, and an effective stump speaker," Cochran wrote in his memoirs. In January of 1830, Senator Benton had arranged for Gentry to be appointed Columbia's postmaster, which made his tavern and home one of the hubs of the town's civic life.
     Unhappily, the Colonel was "loud in his denunciations of the church and its doctrines and practices." And in Columbia, what Richard Gentry said mattered. If his opposition could be blunted, the church would gain some breathing space. If he could be won over, then the battle might begin to turn.

IN THE  late spring of 1830, Colonel Gentry left Columbia to join a caravan traveling to Santa Fe. His absence freed Ann to attend services regularly. Rev. Cochran foresaw great things. "The Holy Spirit awakened in her, and was gently drawing her to Christ." He understood that she and her sister Sophia met often in their houses "and talked of the life Jesus gives and the way to obtain it." 
     "The life Jesus gives" is a phrase worth considering from Ann's perspective. It was not the life her husband was living. He had killed a man. He had squandered his patrimony in speculation. He enjoyed the company of gamblers. Hard drinking with other men was a mainstay of his social life. Once, while riding a borrowed horse to St. Louis, he had overreached in passing a whiskey bottle and tumbled to the ground, losing the horse, saddle and all. Certainly it is possible for a wife to continue to love a man after she discovers his faults, but at 38 Ann Gentry was no longer an impressionable girl. She had seven children to raise and an eighth on the way. Given Richard's frequent absences from home, she must also have been the principal proprietor of the tavern and administrator of the post office.
     She listened closely to Rev. Cochran's sermons. She heard him stress the church's interest in promoting responsible behavior, "the walk and conversation," as he put it, befitting Christian men and women. She knew that the elders of a Presbyterian congregation watched over unsteady members and reproved them for drinking, gambling, or fighting. When she talked with her sister Sophia about the life Jesus gives, she was considering eternal matters, surely; but she must also have been considering how life in her family would improve if Rev. Cochran could help her slip God's bit between her husband's teeth.

RICHARD GENTRY returned from Santa Fe triumphant early in the fall. He had made good money on the goods he carried west, and invested the profit immediately in forty Mexican mules. Eager to reach home in time to witness the birth of his next child, he didn't wait for the caravan to return to Missouri. Instead, he bought a bay mare and corralled her with the mules for a few days, then saddled her, opened the gate, and rode away. It was a solo journey that would have impressed Daniel Boone himself. Men traveling the Trail, even in sizable caravans, risked death by snakebite, dehydration, or starvation. Four had been killed in Indian attacks during the previous two years.

     To Gentry's relief, the mules had followed the mare. "At night," he wrote in a letter to his father, "I picketed the mare so she could graze, and the mules stayed close by." 

I wrapped up in my blanket and slept on the ground, with my faithful dog on guard; of course I kept my gun, pistols and knife handy. I killed deer, buffalo and wild turkeys on the way, which I ate with a relish, as I carried a sack of meal and a sack of salt. I had no trouble striking fire with my flint, and I found fresh water most all the way along the trail, got thirsty only twice.

He arrived before his son was born. Ann wanted to name the boy Nicholas Hawkins Gentry, after her father, who had died during the horrible year at Smithton. Richard insisted on Thomas Benton Gentry. "A fine name for a fine boy," he said. "With such a name, he may be president some day."
     After he reached Columbia the exhilaration of life on the trail evaporated. In his absence, the voters had turned him out of his senate seat, replacing him with a physician, Dr. William Jewell. Nathaniel Patten, the Yankee editor who had labeled the shooting of Henry Carroll a "dastardly murder," had moved to Columbia, bringing the Intelligencer with him. These men and others like them, soft-handed professionals with shelves full of books, were steadily gaining influence. To be born in a canebrake and rocked in a sugar trough for a cradle no longer meant what it once did.
     In his own home, Old School Presbyterianism had become precious to Ann and Analyza, a treasure they could share with each other, but not with him. The younger girls, too, were being drawn that way. He would not or could not forbid his wife and daughters to attend services, but he did what he could to prevent them from meeting with William or Eliza Cochran socially. As for himself, he stiffened his refusal to be introduced to the missionary. If Cochran entered a room, Gentry stood up immediately and left it.
     How Ann and Analyza wore Richard down we don't know. He could be a stubborn man, but these were formidable women, firmly allied. He can't have relished the prospect of becoming a marginal figure in his own household. Eventually, he offered a compromise. Yes, he agreed, all the family would begin to attend church together on Sundays-as visitors. He would even go with them to Cochran's preaching twice a month, provided that they would agree to come with him to the New Light preaching on the alternate Sundays.
This compromise lasted only a few weeks before a New Light preacher approached the Colonel and urged him to abandon it. He should commit himself fully to the New Light church. If he would, the New Lights would happily make him a minister, a role in which they were sure he would be a great success, both because of his stature in the town and his ability as a speaker. Gentry was nonplussed. "Good God!" he replied. "I am not fit to join any church, let alone to become a preacher." The preacher assured him that he needed no special qualifications or training. "All you have to do is believe that Jesus is the Son of God, be immersed, and reform your grosser vices." He left the Colonel thinking.
     The following Sunday, Gentry was up and dressed early, pacing the rooms of the Gentry Tavern. From time to time, he called for Ann and the girls to stop their primping. When they appeared he asked them, "What church shall we go to today?" They were too surprised to answer: this was, by agreement, a New Light Sunday. But the Colonel had a suggestion: "Suppose we go to Cochran's preaching." And so they did. That morning Gentry not only acknowledged Cochran's presence, but shook his hand and talked with him civilly.

THREE YEARS passed. Columbia merchants made fortunes in the Santa Fe trade. Brick and clapboard buildings began to appear among the log cabins. With Franklin at last completely underwater, Columbia had become a magnet for those who wanted the advantages of life in a busy town. Judge David Todd, brother of North Todd, moved his large family into an enormous house with a ballroom. In holiday seasons fashionable Columbians danced minuets there, or Virginia reels, while Todd's slaves fiddled. The Todd daughters gathered friends from the neighborhood and performed amateur theatricals.
     Adults, too, caught the enthusiasm for drama. The courthouse was still an unadorned brick barn, but inside it a thespian society produced comedies that had been popular a half-century earlier in London, "admission fifty cents, children and servants half price." There were band concerts in town and singing societies. There was a literary society and a reading room "furnished with the most approved periodicals and authors upon the Arts, Sciences, and General Literature." George Caleb Bingham opened a portrait studio, and Kentworthy the Ventriloquist threw his voice around McClelland's tavern.

     IN JANUARY, 1832, Richard Gentry had been promoted to Major General in the Missouri militia, and the following summer the Governor had ordered him to lead a thousand men into northern Missouri to fend off possible attacks by followers of the Sauk war chief Black Hawk. As it turned out, Black Hawk never entered the state, and the principal hostilities Gentry witnessed during a three-week campaign were payment disputes between the quartermasters and the merchants who supplied them. Nonetheless, being referred to as "General Gentry" added sheen to his reputation.
     His financial affairs had improved enough for him to move his tavern into a new brick building at the corner of Ninth and Broadway. Half a mile south of the new tavern he and some partners built a first-rate circular racetrack. The track became an annual stop on a racing circuit that attracted horse traders and gamblers from hundreds of miles away. The gamblers wore high black boots and silk shirts with jeweled pins and heavy cufflinks. Their fingers were thick with gold rings. General Gentry enjoyed their company.
     In October, 1833, four days of racing were planned, but the Presbyterians had scheduled their Synod meetings to coincide with the races. This put Gentry in an awkward position. Ann and Analyza would want him at the services; his partners and friends would expect him at the track.
     On Thursday the 17th, the first day of both meetings, a wet snow fell on Presbyterians and gamblers alike. Ann and Analyza went to church in the morning. Gentry went to the race and found a boisterous crowd despite a sloppy track. In the evening, the Presbyterians moved to a campground north of town, where Ann and Analyza heard a passionate sermon and answered the call to move up to the "inquirer's bench" to receive special prayers and instructions. They were seriously considering committing their lives to Christ. Elsewhere, perhaps in the tavern, Gentry and his friends played cards.
     Friday morning, again, the family went their separate ways. After the sermon another of the Gentry girls joined Ann and Analyza on the inquirer's bench. When Gentry reached home that afternoon, the women assailed him in earnest and extracted a promise that he would give up his evening card game and attend the service instead. That evening, while the preacher warned that "the wages of sin is death," the General lolled on the bench, displaying his indifference. After the sermon, Ann went to the inquirer's bench with three daughters and two sons. The General sat alone. When they returned to the tavern, the family pressed him hard for a promise to attend the next morning's service, which he gave reluctantly.
     By Saturday morning the rains had ended. A great stakes race was scheduled, and friends came to the tavern early to collect the General and accompany him to the track. If he had put on his hat and overcoat and joined them, Ann or Analyza might have intervened to remind him of his promise, so Gentry sent his friends away. Then he took his hat and overcoat upstairs and, making sure that he wasn't observed, dropped them out a window into the back alley. When he believed the vigilance of the women had relaxed, he slipped out, retrieved the hat and coat, and returned to the track.
     At the race he cheered and tried to enter into the spirit of the occasion, but at odd moments, his friends would find him frowning: "General, what is the matter with you? You do not seem to enjoy the sport." The crowds were unexpectedly thin for the big day, the betting light. The out-of-town gamblers blamed the Presbyterian fanatics, who had gone so far as to schedule a Temperance Society meeting for eleven o'clock. Despite the sunny skies, the day became so dull that racing was suspended at noon. The gamblers packed up and moved on, and Gentry had to decide what to do with himself.

THE REST  of the story is best told by Rev. Cochran:
"The General was a miserable man; he felt mean; he had violated his promise to his wife and children. The declaration of God continued coursing through every avenue of his soul: 'the wages of sin is death.' He felt like a truant boy and acted like one: he loitered around, wanting to go home and yet ashamed to meet the loved ones he had deceived. He stood on the corner and there resolved to go home, make confession of his wrong and promise to go with them to the meeting.
     "He went home, all was serious and solemn; he hurried out his confession and promise; everyone received him pleasantly; not a word of reproach was uttered by any of them, nor any allusion to what he had done and where he had been. His oldest daughter arose and went to him, as he stood in the door and without saying a word put her arms around his neck and kissed him. This melted him to tears; he wept both for sorrow and joy. O what a power there is in kindness.
     "That evening amidst the crowd that filled the house were the General, wife, three daughters and two sons. The audience was as still as the grave and as calm as death: everyone seemed interested; all the services were of this character; every word that fell from the lips of the preacher was eagerly received and was a two-edged sword; it discovered the thoughts and intents of their hearts. Some forty or fifty occupied the seats of the inquirers. The General's wife, daughters and sons were among the inquirers; he sat in the corner to the right of the pulpit greatly agitated and yet endeavoring to conceal his feelings; he did not go to the inquirer's seat.
     "After the benediction was pronounced (which was at 9 o'clock, the hour we generally closed the meetings) as the congregation was beginning to move out slowly and reluctantly, Bro. Cowan commenced to sing 'O there will be a mourning at the judgment-seat of Christ,' etc. The whole congregation swung back into their seats; many sobbed aloud; the feeling was intense. The General arose, and literally over the heads of the men (for they had seats of planks laid on logs), made his way to where his wife was sitting, and burst out in a loud cry. This added to the intensity of the feeling; he took his seat alongside of his wife and daughters.
     "Mr. Cochran was sitting upon the platform bathed in tears, with his head down; he felt some one touching him on the shoulder, he looked up and there stood the General with tears coursing over his cheeks and his hand extended, which was at once grasped; he said 'I have been your enemy, you are right, I am wrong, forgive me the injury I have done you'; this was done amidst sobs and deep emotion. Mr. C. with choked utterance made the Christian response.
     "The General then went and took his seat alongside his wife and daughters; Mr. C. talked with him urging him to clear all just now, and go to Christ. His mind was dark; he said he felt his sinfulness and need of a Savior, as he had never done before. He was urged to erect the family alter that night before he went to rest. He gave a reluctant promise that he would try. Mr. C. went to the eldest daughter, who was then entertaining a hope in Christ, and told her of her father's promise to try and pray with the family before going to rest, and requested her to aid him in the fulfillment of his promise; she promptly replied that she would. Quite a number of others came forward. The meeting was continued until 11 o'clock; several efforts were made to adjourn the meeting, but without effect. All went home solemn and thoughtful; no loud talking or laughing was heard.
     "When the General and family got home with their friends from the country who were attending the meeting, there was a silence; none seemed disposed to break it; at last he said: 'Well, I suppose it is time to retire.'
     "The daughter spoke up and said, 'Let us have a prayer before we retire. I will read a portion of Scripture, and you, father, lead us in prayer.' The Bible was at hand; she read a few verses, when they all knelt down and the father prayed, and this was the substance if not the very prayer: 'O Lord God Almighty, have mercy upon me and my family and friends for Jesus sake; Amen.'"

Notes
     On Gentry's horse-racing and his joining the Presbyterian Church, North Todd Gentry, "His Life Had Kentucky Flavor" Columbia Missourian, June 27, 1942. On Gentry's falling from a horse while passing a whiskey bottle, George T. White, "George Tompkins and General Richard Gentry," Columbia Missouri Herald May 10, 1901. On his joining the Temperance Society, Missouri Intelligencer, March 24 and May 10, 1832.
     Richard Gentry's letters from the Santa Fe Trail can be found in the Mary Paxton Keeley Papers (WHMC, Columbia, C848, f. 1). Richard Gentry's letters from the Santa Fe Trail can be found in the Mary Paxton Keeley Papers (WHMC, Columbia, C848, f. 1). Somewhat different accounts of the removal of Andrew Broaddus's arm can be found in the Gentry Book, Josiah Gregg's Commerce of the Prairies (Philadelphia: J. W. Moore, 1844), Alphonso Wetmore's Santa Fe Trail and Santa Fe Trade, (1828, 1914), and  Kit Carson's Own Story of His Life (Taos, NM:  1926).
     North Todd Gentry's story of Cochran's stay at Gentry's tavern appears in an interview (Gentry Family Collection, WHMC, Columbia, C4026, f. 2), as does his version of the story of the General's sneaking out the races in 1833. North Todd Gentry also provides the most vivid account of Ann Hawkins Gentry's wild ride on the racing mare in 1819 (Gentry Family Collection, f. 112). The description of social life in the David Todd household circa 1832 is drawn from Anne E. [Todd] Campbell's memoir "When Judge David Todd Danced and the Stars Fell" (Missouri Herald, December 21, 1900, copied in the North Todd Gentry Collection, WHMC, Columbia, C49, f. 40). The same source also documents the friendship between the Todd and Patten families.
     The principal source for William P. Cochran's work as a missionary in the Columbia area and for General Gentry's conversion is "Reminiscence of Presbyterianism in Missouri," a series of articles printed a Columbia newspaper circa 1876 and collected in the scrapbook of Mary Todd Gentry (WHMC, Columbia, C2153). The articles are signed Senex; internal evidence shows that Senex is Cochran himself. I have not been able to locate these articles in any newspaper archive. In the long quotation that ends the section, I have silently corrected what I take to be a few compositor's errors.

© 2010 by Douglas Hunt