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During their outlaw careers, the James brothers and the Younger brothers dealt in fine-blooded stock, raced thoroughbreds and rode beautiful American Saddlebreds. All were expert horsemen, always paying careful attention to their animals, which were essential tools of their ‘business.’ Also essential to the West’s most famous outlaw brothers’ success was the support of a circle of trusted friends. Included in those supporters were such prominent and influential families as the Hudspeths, who raised stock and bred horses on their vast landholdings in JacksonCounty, Missouri. Among the most outspoken was Virginia-born newspaper editor John Newman Edwards, who had been Confederate General Joseph O. Shelby’s adjutant during the Civil War. Edwards’ printed words provided alibis and excuses for the James-Younger Gang, which was seen by him and many other Southerners as a collection of well-liked former guerrillas forced into living outside the law by a repressive Republican Reconstruction federal government.

After the Civil War, other ex-guerrillas — who had ridden with the notorious William Quantrill and ‘Bloody Bill’ Anderson — were as well known as the Jameses and Youngers. Some were recruited as gang members. These men were not only known in Missouri but also in a wide area across the South from Kentucky to Texas. The gang’s base, where the leaders recruited and planned, was the farm of Frank and Jesse’s wealthy uncle, George W. Hite, at Adairville, in Kentucky’s Logan County, 10 miles from Russellville, scene of an 1868 bank robbery. The James boys’ father, Robert, was born in Logan County and graduated from Georgetown College near Midway, Woodford County. Their mother, Zerelada Cole James Samuels, was born at Midway. After meeting and marrying in Kentucky, they had moved to Missouri in the early 1840s.

From February 13, 1866, through the September 7, 1876, Northfield raid in Minnesota, the James-Younger Gang reportedly robbed 12 banks, five trains, five stagecoaches and the gate cash box of the ticket booth at the Kansas City Exposition. A network of friends showed sympathy and support for Frank and Jesse even after the famous fiasco at Northfield. Others, though, turned against the boys — not only those people who could no longer see them simply as ‘victims’ of Northern aggression and big business, but also personal acquaintances and even some new gang members.

In such a dangerous line of work, the old gang could not last forever. Gang member Oll Shepard was killed in 1868 at Lee’s Summit. Brothers Bill (‘Bud’) and Tom McDaniel were captured and killed in 1874 and ’75, respectively. Tom Webb, alias Jack Keene, was captured in Kentucky with Tom McDaniel. Up in Minnesota, Clell Miller, Bill Chadwell (alias Bill Stiles) and Charlie Pitts (alias Sam Wells) were killed, while brothers Cole, Jim and Bob Younger were wounded, captured and imprisoned for a quarter of a century in the state penitentiary. Thus, in 1879, when Frank and Jesse James resumed their criminal careers in Tennessee and Kentucky, no old gang members were available. The loyal network of friends, however, provided them alibis and gave them sanctuary as Frank and Jesse lived freely using aliases — ‘Ben J. Woodson’ and sportsman ‘Tom Davis Howard.’

The James-Younger Gang always rode in style. Newspaper accounts of the gang’s robberies often reported that the outlaws were mounted on the finest horseflesh in Kentucky. The boys took great pride in their horses, too. According to the Little Rock Daily Gazette, when traveling on a raid, the gang usually rode ‘two abreast about one hundred yards apart. One man would lead a horse, and he being the odd man, would ride at the rear.’ This practice, which allowed one horse to rest while the others were ridden, was mentioned by eyewitnesses after the train robbery near Gads Hill, Mo., on January 31, 1874.

All along their routes, the outlaws conducted themselves as gentlemen, paying for everything they received and not drawing attention to themselves. As no photographs of them were yet published, they could take on any identity they wished. While traveling — to such places as Columbia, Ky., in April 1872; Adair, Iowa, in July 1873; Corinth, Miss., and Muncie, Kan., in 1874; and to the new bank at Huntington, W.Va., in September 1875 — they used maps and a compass and, to be on the safe side, avoided well-traveled roads. Daniel Webster ‘Kit’ Dalton, a former guerrilla and gang member and the author of Under the Black Flag, said that he supplied information for the Corinth bank robbery and also rode with the gang when it was operating in Missouri, Kentucky and Texas. The boys did get around and were always prepared for trouble, each member wearing as many as three revolvers and carrying rifles and shotguns in their saddle scabbards. After their crimes, they could always count on family and friends to provide hideouts and support.

The James and Younger boys considered themselves sporting men (Frank and Jesse’s cover in Nashville from 1877 to 1881; Jesse James was co-owner of the racehorse Jim Malone, which won $5,000 in 26 starts in 1880-81). Alexander Frank James, who was born on January 10, 1843, and Jesse Woodson James, who was born on September 27, 1847, learned to ride and appreciate horses in the 1850s — and those lessons paid off in the 1860s. During the war and their postwar criminal careers, good horses meant the difference between freedom and capture, life and death. Horses were also a lot of fun. Frank and Jesse were no strangers to the health resorts frequented by the wealthy sporting crowd of their day — such as Monegaw Springs in St. Clair County, Mo., and Hot Springs, Ark., where there was horse racing. The Daily Gazette and John Gould Fletcher’s book Arkansas reported that the outlaws had been seen at the springs before the January 15, 1874, stagecoach robbery on the road between Hot Springs and Malvern, Ark. By the early 1870s, Frank and Jesse were also going to Saratoga Springs, N.Y., and Long Branch, N.J., (Monmouth Park racetrack opened near there on July 30, 1870) to run their thoroughbreds. A picture of Jesse was taken at the Long Branch resort. Records in Kirk’s Guide to the Turf show Jesse James’ horse Skyrocket, which was foaled on April 12, 1873, near Midway, Ky., raced at Monmouth Park in 1875-76.

In the meantime, the Youngers were racing thoroughbreds in Missouri, Louisiana, Texas and Indian Territory (present-day Oklahoma). Their knowledge of racehorses also went back to their childhood. According to the March 26, 1874, Louisville Courier-Journal and the May 8, 1901, Chicago Tribune, their grandfather Charles Younger, who had moved his family to Crab Orchard, Ky., from Virginia, was a man ‘of wealth and sporting proclivities, owning stock, and of the anti-emancipation aristocracy.’ The family eventually moved to Missouri, where Charles’ son Henry Washington Younger married Bursheba Fristoe of Independence in 1830. The family home (and Cole Younger’s birthplace) was Big Creek, southeast of Lee’s Summit.

Sometime in 1869, according to an article in the March 27, 1875, Chicago Tribune, a horse race led to some trouble for Cole Younger in Louisiana, where he had lived for a time shortly after the Civil War and still had plenty of friends. Younger, according to the article, put every dollar he had — $700 — on his own horse, ‘one of the famous long-limbed, blue-grass breed of racers, an animal not fair to look upon but of great speed.’ Younger’s horse had a comfortable lead until someone came out of the crowd waving a cloth, causing the horse to lose its stride and finish second. When Younger refused to pay up, he found himself opposed by an angry mob. His response, according to the newspaper, was to draw two Dragoon revolvers and empty them into the crowd before dashing away. ‘Three of the crowd were killed outright, two died of their wounds, and five carry to this day the scars of that terrible revenge,’ the newspaper reported, adding that the deadly affair previously had been ‘apparently overlooked in the crimes attributed to [the Youngers] by the press.’ Whatever happened that day didn’t keep Cole Younger out of the state. According to a letter published in the November 30, 1874, St. Louis Republican, Cole claimed that he was in Louisiana’s Carrol Parish from December 1, 1873, to February 8, 1874, and thus could not have participated in three alleged James-Younger crimes — stagecoach robberies at Shreveport, La., (January 8, 1874) and Hot Springs, Ark., and the train robbery at Gads Hill, Mo. That March, the Louisville Courier-Journal ran an article stating that Cole and his brothers ‘all are good-looking, manly, and to a certain degree accomplished gentlemen. They would be accepted at any hotel or on any Mississippi steamer and hardly [be] taken for what they are — desperadoes without pity or fear.’ In short, the Younger boys, like the James brothers, had solid roots and were anything but antisocial loners. They were well educated and of aristocratic origin, with the manners of gentlemen. One of those gentlemen, John Younger, the brother of Cole, Bob and Jim, was killed by a Pinkerton Detective agent in a shootout near Monegaw Springs on March 17, 1874.

The James-Younger connection with Joseph Orville Shelby is well known. Born in Lexington, Ky., in 1830, Shelby was a boyhood playmate of John Hunt Morgan, who became a prominent Confederate raider in Kentucky. Shelby, whose family was related to the first governor of Kentucky, Isaac Shelby (1750–1826), rose to brigadier general in the Confederate Army. He served in every major Civil War campaign west of the Mississippi River, including the disastrous Missouri campaign in 1864. John Newman Edwards, whom he had befriended in Lexington, became his adjutant. Both Shelby and Edwards came to admire the courage of Frank James and the other Missouri guerrillas who were resisting Union forces. Frank was one of the guerrillas who saved General Shelby from capture on December 7, 1862, at the Battle of Prairie Grove, Ark. After Confederate General Robert E. Lee surrendered in April 1865, Shelby relocated to Mexico to offer his military services to Emperor Maximilian. Although Maximilian was soon shot by a firing squad, Shelby prospered in Tuxpan, Mexico. In 1867, he returned to Missouri, still a Confederate at heart. Almost certainly he harbored Frank and Jesse James when they were being pursued. Shelby owned 1,000-acre Travelers Rest, nine miles from Lexington, Mo., in Lafayette County, and he also owned 960 acres at Adrian in Missouri’s Bates County. He was one of the largest wheat growers and landowners in the state.

When Frank James went to trial in Gallatin, Mo., in August 1883 for his actions (he had allegedly killed passenger Frank McMillan) during the July 15, 1881, Winston, Mo., train robbery, Edwards was still urging in the newspapers for all to be forgotten and for Frank to be acquitted. And Shelby was still in Frank’s corner, testifying as a character witness for his old friend. Shelby said that he had seen Jesse James in November 1880 but hadn’t known that Jesse was wanted by the authorities. Shelby added, ‘The last time Jesse was at my house was at Page City, in the fall of 1881, where I saw Frank James in 1872, which was the last time I saw him.’ The lead prosecuting attorney, William H. Wallace, questioned Shelby about a waybill the old general had signed for Frank’s wife, Annie Ralston James, in the spring of 1881. Drunk at the time of his testimony, Shelby didn’t like that line of questioning and threatenedWallace. The next day, he apologized to the court for his earlier behavior, but Judge Charles H.S. Goodman still fined him $10. After court had finished, Shelby again tried to intimidateWallace, this time outside the courtroom.

In 1894, President Grover Cleveland appointed Shelby the U.S. marshal for the Western District of Missouri. Shelby died in office on February 13, 1897, at Adrian and was buried with full military honors in Kansas City’s Forrest Hill Cemetery on February 17. ‘Thousands of people lined the streets through which the procession passed,’ the Lexington Morning Herald reported the next day. ‘The sermon was preached by Rev. S.M. Neil of the Presbyterian Church and there was an address by Judge John Finis Phillips of the U.S. Circuit Court, a lifetime friend of the deceased.’ Judge Phillips had been part of the legal team at Frank James’ trial in Gallatin, and in 1915 he would give the eulogy at Frank’s funeral.

Far less well known is the James brothers’ connection with James H. Workman, a prominent resident of Union Township in Missouri’s Nodaway County. The parents of James Workman were among the first settlers of Nodaway, having migrated there from Indiana. James became a noted horse breeder, and his brother William was a wealthy landowner and respected citizen in the county. Although perhaps somewhat reluctantly, James Workman bought and dealt in blooded horseflesh with the James-Younger Gang, which paid him in $20 gold pieces. The gang sometimes camped in thick timber near Clear Creek, which bordered the Workman farm, west of Pickering. Four gang members, most likely Frank and Jesse James, Cole Younger and Clell Miller, may have been at that location before riding north into Iowa in early June 1871 to rob the Ocobock Brothers’ Bank in Corydon.

The gang’s inner circle of friends also included, to name a few, Howard County (Mo.) resident John McCorkle, an ex-guerrilla who had befriended Cole Younger and Frank James and later wrote Three Years With Quantrill; former Confederate Colonel Robert McCulloch, who lived near Boonville, where ‘The Great Cole Younger and Frank James Historical Wild West’ show performed on September 2, 1903; former Confederate Captain Warren Carter Bronaugh, a Missourian who worked hard to get the Younger brothers paroled from the Minnesota State Penitentiary at Stillwater; and, as mentioned earlier, the extended Hudspeth family of the ‘Six Mile Country’ (between Independence and Lake City) in Jackson County, Mo.

According to Through the Years With the Hudspeths, a three-volume family genealogy by Anna Ford, Major William Hudspeth had migrated to Missouri by 1828. He had been a soldier in both the Revolutionary War and the War of 1812 and had founded Franklin, Ky. William was also considered a sportsman, bringing with him to Missouri a fine collection of foxhounds (the Hudspeth hounds later became famous, thanks to the efforts of a grandson, Thomas Benton Hudspeth). The major and his wife, Tabitha, whom he married in 1801, had 11 children — Nathan Beall, Thomas Jefferson, Sylvia, Joseph W., Missouri L., Silas Burke, Benoni Morgan, Joel Ephriam, George Washington, Robert Nichols and Malinda Paralee. The Hudspeth Settlement, as it was first known, was established at what is now Lake City, Mo. Robert Nichols ‘Bob’ Hudspeth, who never married, gave land for the small town. His house was about eight miles northeast of Independence. When he died in 1885, he owned 1,500 acres of land, which was being used for raising stock and farming. During the Civil War, Robert Hudspeth had served briefly with Quantrill, and Frank James was a good friend. Robert and brother Silas, who owned a 120-acre farm, supplied the James-Younger Gang with valuable horses and allowed their homes to be used as hideouts. Frank James’ only son, Robert Franklin (1878–1964), was named for Robert Hudspeth, according to descendant Joe Elsea, whose great-grandfather was Joel ‘Rufus’ Hudspeth (1839–1895).

Rufus Hudspeth was one of the children of Joseph W. Hudspeth, who had married his first cousin Amanda in 1830 and become a prosperous Jackson County farmer. After Amanda died in 1850, Joseph married Louise (Rice) Brown, and they had one more child — Joseph Lamartine (‘Lam’) Hudspeth. Rufus, who played with Frank and Jesse when they all were schoolboys, was one of several Hudspeths to serve in Quantrill’s guerrilla band, while other family members harbored the Rebel raiders. Rufus also later served under General Shelby and Maj. Gen. Sterling Price. After the war, Rufus went to Kentucky with Quantrill, but he returned to Missouri in 1865, married Sarah Franklin the next year, had four children — Joseph, Mary Amanda (Elsea), Elvira Beall (Chiles) and Charles B. — and became a prominent farmer and stockman. Rufus’ brother William Napoleon ‘Babe’ Hudspeth also served with Quantrill. After the war, Babe married Nannie Ragland of Independence and built a large two-story Victorian home that still stands in Lake City, which was then a thriving community with stockyards and a racetrack.

Other sons of Major William Hudspeth living nearby included George Washington Hudspeth and Joel Ephriam Hudspeth, who inherited the family farm. An 1877 history of Jackson County states: ‘It is probable that no finer nor a more extensive view of the surrounding country can be obtained than from the hill upon which the residence of Joel E. Hudspeth is located. It overlooks the Valley of the Blue. Its landscape is in its rural beauty.’ Many of the Hudspeths vacationed at Monegaw Springs, where James-Younger Gang members were known to hang out.

A strong connection between the gang and Hudspeths, if not already known by the authorities, became obvious from the testimony of former gang member James Andrew ‘Dick’ Liddil at the 1883 Gallatin trial of Frank James. Liddil, who once rode with Quantrill, had been part of Jesse James’ new gang, beginning with the October 8, 1879, train robbery at Glendale, Mo., and then had surrendered to the sheriff of Clay County on January 24, 1882. Liddil told the law most of what he knew about the gang, but his surrender was not publicized, so as not to alert Jesse James. The news didn’t become public until March 31. At his St. Joseph, Mo., home on the morning of April 2, 1882, Jesse read about it and supposedly commented that Liddil was a traitor who deserved to be hanged. Shortly thereafter, Bob Ford fired a shot heard around Missouri and beyond — the ball struck Jesse in the back of the head, killing the famous outlaw.

During his testimony at Frank James’ trial in 1883, Liddil said that after the Glendale train robbery, he, Jesse James and Ed Miller rode into the Six-Mile Country and went to Bob Hudspeth’s farm. From there, Liddil said he traveled about two miles to the 40-acre farm of Lamartine Hudspeth. Liddil had worked for Bob Hudspeth in 1870–75, and he testified in 1883 that he had lived at Bob’s ‘off and on for nine years.’ There, he added, he had become acquainted with John Younger and Jesse and Frank James, who often stayed around ‘a day or a night or two nights.’ Liddil told of the time he had been ‘riding a horse of Bob Hudspeth’s, which I had [taken to] Lake City for the purpose of running a race.’ He ran two heats before he was chased from the area by Deputy Marshal Ed Lee. Liddil then returned to Bob Hudspeth’s home to put the horse in the stable. From there, Liddil’struck out on foot, and next day went to Ben Murrow’s [place], who knew I was dodging the officers, and bought a horse from him in trade.’ Ben Hudspeth Murrow’s mother was Major Hudspeth’s oldest daughter, Silvia. During the war, Ben had served under General Shelby and had later joined Quantrill. Liddil also said that in 1879 he met with Jesse James, Wood Hite, George Hite, Ed Miller, Daniel ‘Tucker’ Bassham and Bill Ryan at Murrow’s 56-acre home (built by the Hudspeths in 1830) west of Buckner, Mo. Ben Murrow would be a pallbearer at the 1882 funeral of Jesse James and the 1915 funeral of Frank James.

Lamartine Hudspeth (1858–1915) also received further mention in Liddil’s testimony. Liddil said that he bought a chestnut sorrel horse from Lamartine before the Winston train robbery on July 15, 1881. Lamartine lived in Lake City, but he owned a beautiful racing stallion named John Morgan and he attended horse races at Louisville and New Orleans. In The Complete and Authentic Life of Jesse James, Carl Breihan noted that a fresh horse was always waiting for Jesse at the Hudspeth stable. ‘On some mornings when Lamartine went out to the barn,’ Breihan wrote, ‘the fresh horse was gone and standing in its place was a tired animal that Jesse [or Frank] had left.’ After Jesse James was killed, Lamartine Hudspeth was one of the people called upon to identify the body. Lamartine later ran into his own serious trouble with the law. On November 25, 1899, he went on trial for killing Joe Kesner, a married railroad station agent who had apparently been showing too much interest in Lamartine’s niece. Lamartine’s attorney was Arthur N. Adams, considered the best in Jackson County at the time, and Lamartine was acquitted.

The Hudspeths sometimes bred their horses with the horses of another prominent Jackson County family, the Chiles. Jim Crow Chiles and Kit Chiles were both members of Quantrill’s raiders, while William Chiles was an early member of the James-Younger Gang. Bill Chiles was one of the men suspected of holding up the Clay County Savings Association bank in Liberty, Mo., on February 13, 1866. Although Jim Crow Chiles may never have ridden with the James boys, he became involved in a dispute with gang member and ex-guerrilla Payne Jones, whom he caught stealing a valuable horse from him before the gang robbed the Daviess County Savings Association in Gallatin on December 7, 1869. Jim Crow’s name also surfaced after the ticket booth at the Kansas City Exposition was robbed on September 26, 1872. Jesse James was one of the accused men, prompting him to write a letter to the Kansas City Times in October, denying his involvement. Among other things, Jesse wrote: ‘It is generally talked about in Liberty, Clay County, that Mr. James Chiles, of Independence, said that it was me and Cole and John Younger that robbed the gate, for he saw us and talked to us on the road to Kansas City the day of September 26th. I know very well that Mr. Chiles did not say so, for he has not seen me for three months, and I will be under many obligations to him if he will drop a few lines to the public, and let it know that he never said such a thing.’ Jim Chiles did respond with a letter, in which he denied seeing Jesse or the two Youngers on or near the date of the robbery. That November, Cole Younger wrote a letter to the St. Louis Republican denying his own involvement, but in detailing his movements on the day of the robbery, he said he had had a long talk with Chiles at the Big Blue River and had spent the night at Silas Hudspeth’s place in Jackson County. Bill Chiles’ son, Ike, was in the Saddlebred business for many years. One horse bred by the Chiles family was known as Jesse James’ Mare. They also bred the Saddlebred mare Mary Low, whose sire was Lamartine Hudspeth’s stallion John Morgan.

After Jesse James was killed, the Hudspeths continued to support Frank James. Frank’s 1883 murder trial in Gallatin, Mo., lasted 16 days, and he was acquitted after the jury deliberated for 3 1/2 hours. Because Dick Liddil had implicated Frank in the March 11, 1881, holdup of a paymaster in Muscle Shoals, Ala., Frank also stood trial in Huntsville, Ala. That trial lasted 10 days in April 1884, and again Frank was declared not guilty. Once back in Missouri, he faced charges for the July 7, 1876, train robbery at Otterville, because a captured gang member, Hobbs Kerry, had fingered him long ago. However, just two days before the trial was scheduled to begin in Kansas City in February 1885, the case was dropped because evidence was missing and there were no living witnesses available. Frank James was now clear of all charges in Missouri, and newly elected Governor John Sappington Marmaduke, a onetime Confederate general, had no intention of turning the former guerrilla over to Minnesota authorities to stand trial for the Northfield robbery. Marmaduke, according to newspaperman Edwards, had merely advised Frank to go to work on a farm and ‘to keep out of the newspapers. Keep away from fairs and fast horses, and keep strictly out of sight for a year.’

Over the next 30 years, Frank James would continue to be welcome whenever he made a visit to one of the Hudspeth homes in Lake City. On January 8, 1897, the former outlaw was in St. Louis when he wrote a letter to Mrs. Malinda Paralee Hudspeth Wood, the youngest daughter of Major William Hudspeth:

Dear Friend, I have just received your favor. It grieves me more than you can imagine to learn of the death of my dear friend. I am anxious to visit the old place before you leave it, from the fact that around that hospitable home of yours, many fond recollections are recalled and were it possible to turn back memories page and live over those happy days again, that big fire in the west room and around it seated Joel, Silas, Robert, George, Rufus, Babe, Lamartine, Ben Murrow and the others would be a picture that would gladden the heart of all. But as this cannot be, I hope that when I do come, I will have the pleasure of meeting all those that are living around that same dear old hearth. It will not be so very long before the restless flapping of death wings will no doubt be heard around the persons of many more of our dear friends and so on down to the end of time, one generation after another. My sympathy goes out to you in this dark hour and I trust you will be given courage by the Supreme ruler to bear this burden — as He gave you courage and strength to do so on other occasions. We will give you due notice in advance of what time we will be at your home. Present my regards to Ben, Babe, Lamartine, Uncle George, in fact to all our friends. Mrs. James also joins me in love to all. I am yours most respectfully, Frank James.

George Hudspeth died six years after the letter was written. Babe Hudspeth died in 1907. Malinda Paralee, to whom Frank wrote the 1897 letter, died in 1913, two years before Lamartine Hudspeth and Frank James himself died. Ben Hudspeth Murrow lived until 1916, as did Cole Younger. During their criminal careers and afterward, the James and Younger brothers had an inner circle of good friends, and few were better than the Hudspeths, faithful to the end.

This article was written by William Preston Mangum II and originally appeared in the August 2003 issue of Wild West magazine. For more great articles be sure to subscribe to Wild West magazine today!