Life and Racing Times of Jesse and Frank James (Yes! Those James Brothers)

By Maryjean Wall

Frank and Jesse James, notorious outlaws in the American West in the late 1800’s, were huge fans of racing when they weren’t busy robbing banks and trains. The height of the summer season brought Jesse to Saratoga Springs and Monmouth Park, where he mingled unrecognized among the high-rollers, using an assumed name. The pistol-packing brothers both owned race horses.

The brothers lived and died by the sport, with Jesse shot and killed while wiping the dust off a photo of his favorite horse. Frank, meanwhile, turned from robbery to an honest career as a racing official. Theirs was quite a story in a sport that doesn’t lack for strange tales of the turf.

One often-seen photo of Jesse shows him leaning on a walking stick at Oceanport, New Jersey, the home of Monmouth Park. The photo was taken during a summer when he was racing his horses there and at Saratoga in upstate New York. Jesse, like Frank, appreciated a fast horse. The brothers’ admiration for a good horse was understandable: both depended on fast mounts to carry them quickly from the scenes of their crimes.

The James Brothers of Missouri (1948 film) – Photo Courtesy of IMDB

Their story began when they were young teenagers growing up in the slave-holding border state of Missouri. During the Civil War (1861-1865) they joined up with loosely organized guerrilla fighters and came under direction of the famous fighter, William Quantrill. A group of Quantrill’s raiders was said to have robbed Kentucky’s famed Woodburn Farm of racehorses close to the war’s end, and Frank might have accompanied that group, as he had followed Quantrill into Kentucky from Missouri. Outlaws ranged all over Kentucky and the border states following the war, as malcontents and former soldiers unable to settle back into their former lives pursued violent lifestyles filled with crime.

The Brothers James exploited these unsettled times by robbing stage coaches, trains, and banks in the Midwest, at first riding with Quantrill’s gang. By the year 1868 they had joined up with an outlaw named Cole Younger to rob a bank at Russellville, Ky., and with that the James-Younger gang formed. These miscreants robbed and pillaged their way from West Virginia to Iowa, with side trips through Texas. Someone had to call the law – and someone did.

The Pinkerton National Detective Agency began to hunt down Frank and Jesse in 1874 but the James brothers managed to elude the law. The James-Younger gang finally was torn apart with arrests resulting from an ill-fated bank robbery in Minnesota in 1878, but as usual, the James brothers avoided capture. They were the nation’s “most wanted” — and also the most fascinating to the public for their exploits.

It was about this time that the brothers’ interest in racehorses developed. Jesse and Frank resurfaced in Nashville, Tennessee, under assumed names even as the Pinkertons were searching for them. Jesse and his wife, Zerelda (who was his first cousin) became Mr. and Mrs. John Davis Howard. Frank and his wife, Annie, became Mr. and Mrs. Ben J. Woodson. Soon after the families settled in at Nashville, two boxcars of racehorses arrived for one Mr. Howard (Jesse James).

Jesse (as Mr. Howard) laid out a race track on the farm where he was living and he allowed his neighbors to exercise their horses on his track. Soon he began to enter his horses at regional fairs. On a few occasions, Jesse rode in races on his own horses. But despite trying to settle in at Nashville, he never could put his criminal leanings to rest. “Mr. Howard” would disappear from the farm for weeks, with his neighbors and fellow horse owners having no idea that he was robbing banks and stagecoaches during these sojourns in surrounding border states.

When home in Nashville, Jesse took on partners in racehorses. He raced a decent horse named Jim Malone even as the governor of Missouri put up a $10,000 reward for the arrest of Jesse and his brother Frank. The reward stood out there for the taking, with the ironic twist that no one in Nashville realized the eager new racing patrons among them were the same notorious criminals that the Pinkerton detectives hunted.

Then, in 1882, Jesse was shot and killed. He had relocated his family to Missouri and was having breakfast in his home one morning with the only two men he still trusted, Charlie and Bob Ford. The three men were making plans to rob a bank in Nebraska.

After finishing breakfast, the men moved to the parlor to continue their discussion. Jesse noticed that a framed picture of his favorite racehorse, Skyrocket, needed dusting from its place on the parlor wall. He picked up a duster and stood on a chair to reach the photo when Bob Ford shot Jesse in the back of his head, killing him. Bob applied for the reward. There was no honor among these thieves.

Soon after Jesse’s death, Frank surrendered and underwent two years of courtroom trials. Eventually, and quite astonishingly, he was declared not guilty. He had blamed brother Jesse for their crimes. The not-guilty verdict left Frank a free man, no longer hunted by Pinkertons, and no longer having to use the Woodson alias. He began working at a variety of honest jobs while now known as Frank James. His most interesting job undoubtedly was that of betting commissioner for the man who would be leading trainer in the nation five times, Hall of Famer Sam Hildreth.

As Hildreth’s commissioner, or agent, Frank made Hildreth’s wagers for him so that others would not know which horses Hildreth was betting on as this could seriously affect the odds. Frank began working for the man in 1902 at the Fair Grounds in New Orleans. The two developed a pleasant working relationship.

Later, in a book Hildreth co-authored, titled “The Spell of the Turf,” the trainer praised Frank’s honesty in making wagers for his boss. Hildreth also speculated that Frank had thrived on being a wanted man when no one in racing “had the slightest suspicion who he was. He liked the excitement of being hunted and he especially liked the way he could parade around in the open, right under the eyes of those who were looking for him.”

Frank was a free man in 1889 when he traveled under his own name to the Kentucky Derby, wagering heavily on long shot Spokane, who upset the favorite, Proctor Knott, a horse nearly everyone had thought could not be beat. Frank was also working as a starter at county fair races in multiple states, including Kentucky. He relocated to Missouri in his later years, earning a reputation as a breeder of fine horses.

His life ended with him giving tours of the notorious James brothers’ family farm, charging each person 25 cents admission. He died in 1915, the year Regret became the first filly to win the Kentucky Derby. He was 72, an old man who had lived a life so filled with adventure that his adventures hardly seemed real any longer with all the years that had passed.

The story of Jesse and Frank James truly had been among the strangest among the tales of the turf.