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.

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