The Lawyer Who Took on Jesse James ... and Won

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Henry McDougal.
Photo courtesy
of J. Muehlberger

As bank robberies go, the 1869 heist pulled off by legendary outlaws Jesse and Frank James in Daviess County, Mo., wasn’t much of a success: They may have left with no money, they probably shot the wrong man, and Jesse James lost his horse.

Perhaps even more frustrating for the outlaw duo, they ended up getting sued by a local farmer and his ambitious young lawyer—the first and only successful civil action against the former Confederate guerrillas-turned-outlaws.

The lawsuit hasn’t become part of the Jesse James folklore, but that’s not surprising, say legal academics who study Missouri’s post-Civil War history. At the time, they say, Jesse and Frank James were widely held up as symbols of Reconstruction defiance, and much of what was written about them was embellished greatly or just flat-out fabricated.

Indeed, the details of the James brothers’ botched crime might well have been lost to the ages were it not for the efforts of Kansas City, Mo., litigator James P. Muehlberger. A self-described “history nerd,” he decided to look for the obscure case after hearing about it in the fall of 2006 from the in-house historian at the firm where he’s a partner, Shook Hardy & Bacon.

The young lawyer who took on the James brothers, Henry McDougal, had been a founding partner of the firm, but that’s about all Muehlberger had to go on. By the time he found the original case filings last August, however, he had uncovered a true tale more fascinating than any legend. “It’s sort of the rule of law vs. the outlaw,” says Muehlberger. “McDougal rid Missouri of an outlaw gang that had really been plaguing the state.”

The basic story is simple, but strange. On Dec. 7, 1869, Jesse James killed a cashier at the Daviess County Savings Association in Gallatin, Mo. As the brothers made their getaway, Jesse James got thrown from his horse and dragged in the stirrup. The outlaw untangled himself and jumped onto the horse his brother was riding, abandoning his mount just outside Gallatin, the county seat.

While fleeing to their farm in Kearney, Mo., the brothers—still sharing a horse—ran into Daniel Smoote, a wealthy farmer who happened to be riding his own horse. Since a horse runs faster carrying one man instead of two, Jesse James requested the use of Smoote’s horse—at gunpoint.

Stealing livestock was nothing new for James, but Smoote’s subsequent reaction was. Smoote filed a civil lawsuit (PDF) against the brothers in Daviess County, seeking full value of the horse, saddle and bridle the James brothers had taken.


The brothers, at first, responded in kind: They hired Samuel Richard­son, one of Missouri’s most successful lawyers. He argued that neither brother was personally served notice—although the Clay County sheriff said he delivered the papers to the James family farm—and the case was dismissed on that technicality.

But seemingly offended by the implications, Jesse James proclaimed himself innocent of the Gallatin holdup and murder in a letter to the Kansas City Times, a paper founded to support the Confederate cause. While he admitted that the horse left behind at the Daviess County Savings Association had once belonged to him, James wrote that he had sold it sometime before the robbery to “some Kansas jayhawkers”—a slang term for local Civil War-era antislavery guerrillas. If he could be assured a fair trial on the killing, he wrote, he would gladly stand for one.

The letter, however, gave Smoote’s lawyer, Henry McDougal, another bite at the apple. He petitioned the court to file notice of service in the classified section of another newspaper, the Gallatin Weekly Democrat.

“I think he thought, ‘If you [Jesse James] want to try this in the paper, I’m going to serve you in the paper, because apparently you’re reading it,’ ” Muehlberger says of McDougal. Richardson filed another motion to dismiss, claiming that the James brothers weren’t in Gallatin when the notice was published. But at the next hearing Richardson announced that Frank and Jesse James had authorized him to withdraw their answer, and allow a judgment to be entered against them.

The court awarded Smoote $223, which amounted to the value of the property the James brothers had taken. To collect the judgment Smoote took possession of the horse James left behind at the robbery.

The judgment made Smoote whole, and then some. The horse was believed to be from Kentucky racing stock, and was valued at $500—same as the going price for 50 acres of Missouri farm land. Everyone in Gallatin knew it belonged to Jesse James, who was flush with cash from his earlier and more successful heists. And as such, it may have been the first physical evidence linking Jesse James to a crime.

Although Daviess County officials showed no interest in pursuing the James brothers in connection with the Gallatin murder, state officials—mainly Union sympathizers—were far less tolerant. An arrest warrant for the James brothers was issued by the state for the Daviess County murder. And in January 1870, the governor announced a $3,000 award to anyone who turned them in.

Scholars familiar with the James brothers’ history were surprised to hear about Smoote’s lawsuit. Some surmise that Smoote and McDougal had anticipated that the James brothers would concede their more valuable horse to a default judgment, rather than risk arrest. Others think the lawsuit was really about Unionists asserting their power in that part of the country, which was still smarting from the Civil War.

All agree that Henry McDougal was a brave man. A former Union soldier, he was 25 years old when he took Smoote’s case and had only been in practice 13 months. Later, McDougal discovered that every other lawyer in Gallatin refused to file the lawsuit.

James Muehlberger. Photo by Nick Vedrox

“Daviess County wasn’t about to bring criminal charges, and it’s amazing he would bring a civil suit because these guys even in 1869 were well-known murderers,” says Michael Fellman, a professor at Canada’s Simon Fraser University whose research focuses on the Civil War. “Would you want to take on a gangster?”

More than once Jesse James tried to have McDougal killed, Muehl­berger says, but the gunman missed.

Dick Lidell, a former associate of the brothers who testified against Frank James, told McDougal that his associates shot at the train McDougal rode. Lidell recalled another near miss, Muehlberger says, when McDougal was taking a walk with his wife. Jesse James spotted them, but de- cided not to shoot “either out of a sense of Southern civility, or because Jesse didn’t want to leave a live witness,” Muehlberger says.

But McDougal’s risks were swiftly rewarded. He was elected mayor of Gallatin a few months after he won Smoote’s case. He served two terms, and then was elected as a probate judge. McDougal was also appointed as a special prosecutor in a criminal case against Frank James for robbery and murder, filed more than a decade after Smoote’s lawsuit.


Shook Hardy allows lawyers to take sabbaticals, and Muehlberger decided to take three months off last summer to search for Smoote’s lawsuit.

He had never intended to become so immersed in the case—his initial discussion with the firm historian had been about the later case against Frank James, and how McDougal had been appointed special prosecutor.

“I thought that was interesting so I did some research,” he recalls. “In the course of researching that, I discovered that he had not only prosecuted Frank James, but 12 years earlier filed a civil lawsuit against [the brothers]. I thought, ‘Wow, that’s cool.’ ”

But stepping away from his practice to conduct historical research was nothing he’d ever done before.

Logically, he started at the Daviess County Clerk’s Office, but no one there had ever heard of the action. They told him that everything related to Jesse James was lost, stolen or taken to a nearby bank vault. But given the civil suit’s obscurity, Muehlberger thought that the documents might still be there.

In the 1800s the court did its filing chronologically rather than alphabetically, which added to Muehlberger’s task. Not surprisingly, the files weren’t in perfect order. He almost gave up, but decided to visit the clerk’s office one more time on the last day of his sabbatical.

“They closed the office at 4:30, and it was 4:25,” he says. “I thought to myself that I was going through the last file I’d ever go through, and then I found it.”

The county clerk was as surprised as Muehlberger. The court record, which is around 100 pages, is mostly handwritten. In the complaint, McDougal describes Smoote’s horse as having “four white feet and a white snip on the nose.”

It states that Frank and Jesse James “did feloniously steal, take and carry away the horse from the plaintiff,” who was “in fear of some immediate injury to his person.”

Besides digging through old court files, Muehlberger spent time talking to longtime residents of Daviess County, which is located in northwest Missouri. Through the discussions he found out that folklore surrounding the Daviess County Savings Association rob- bery—which even war­ranted a song, “Jesse James,” sung by artists ranging from Eddy Arnold to the Pogues—is probably in­accurate. Indeed, Jesse and Frank James may have come to Gallatin with no intention of robbing the Daviess County Savings Association.

As the story goes, the brothers planned to rob the bank and kill John W. Sheets, described as a former Union captain who worked as the bank’s cashier. In his research, however, Muehlberger found that Jesse James might have meant to murder another Gallatin resident, Samuel P. Cox. A Union militia colonel, Cox was famous for killing the Jameses’ Con­federate guerrilla leader, “Bloody” Bill Anderson.

The brothers came from a farming family that owned slaves, and Union soldiers had beat and hung their stepfather while looking for Anderson and other bushwhackers on the property. The stepfather survived, and the brothers joined Anderson’s group shortly afterward.

What happened next may have been a case of mistaken identity: Cox and Sheets resembled each other, Muehlberger says, and they worked as cashiers in different banks in nearly identical buildings in Gallatin’s town square. He believes that Jesse James mistakenly shot Sheets, thinking that he was Cox.

Shortly before Jesse James fired his gun, Muehlberger says, he shouted, “This is for the death of Bloody Bill Anderson!”

People also told Muehlberger that the brothers might have left the bank empty-handed. One account has Jesse James asking Sheets to change a $100 bill, as a distraction, and leaving the money there after firing the fatal shot. Others say that he grabbed some “worthless bonds” on Sheets’ desk before leaving.

“Many people just assumed this was a bank robbery gone bad,” Muehlberger says. “My research has convinced me that Jesse went to Gallatin to as­sassinate Cox.”

And Muehlberger points out that there were only two men at the bank robbery, rather than the traditional four. “You needed to have one man to hold the horses and another to prevent people outside from going in,” he says. “You needed to have a third man inside to cover, and a fourth man to have his hands free and hold a grain sack and fill it up with greenbacks.”

After the brothers took Smoote’s horse, they tried to go home in a roundabout way, Muehlberger says, in case someone in Gallatin telegraphed the next town about the crime. They got lost and asked a minister near the town of Kidder for directions. Muehlberger says Jesse James told the man that they had just shot Samuel Cox.


Even the lawsuit may not have been as clear-cut as it seems. McDou­gal and Cox were friends and at one point shared an office. That relationship, some say, could show that Smoote’s lawsuit was about more than just a stolen horse.

“There were political overtones, and there may have been lots of reasons to bring this lawsuit that had nothing to do with collecting a judgment against Jesse James,” says Karl Brooks, a lawyer and history professor at the University of Kansas. Towns near the Missouri-Kansas border were still hurting from the Civil War, he says, which ended five years before Smoote’s lawsuit was filed. Brutal revenge beatings were common, as was property theft.

“It may have been that the Union was back in control of this area, and they wanted to show that they weren’t going to take horse-jacking anymore,” Brooks adds. “Much of this sounds like a gang turf beef to me.”

Hard feelings over the war did influence the actions of Jesse and Frank James, Brooks says, but they also relied on others’ past pains to gain support for their criminal activities, which were financially rewarding.

“James said, ‘If you hate railroads and banks and what they’ve done to society, you’ll never convict me. All I’m trying to do is redistribute the wealth,’ ” Brooks explains.

John Newman Edwards, a former Confederate soldier who founded the Kansas City Times, played a significant role in giving the James brothers a positive spin. Ed­wards started the paper with the intent of returning power to Missouri’s Confederates, and he often wrote about Jesse James in heroic terms. “He made up great stories about them as political bandits, and they kind of liked it,” Fellman says. But he refers to the tales as “fakelore,” adding that “Jesse was definitely a psychopathic guy.”

From his research, Muehlberger agrees with the theory that Confederates romanticized Jesse James to support their cause. Quite simply, the brothers relied on this good press to rationalize continuing their life of crime, Muehlberger says.

Given Jesse James’ popularity with Confederates, it’s unlikely that Smoote, who was also a farmer and former slave owner, was ever in any danger, says Michael H. Hoeflich, a professor at the University of Kansas School of Law.

“Folk heroes don’t shoot farmers,” Hoeflich says. “Killing a farmer is a lot different than knocking over a bank or shooting a prosecutor.”

Jesse James was murdered in 1882 by an associate named Robert Ford. Thomas T. Crittenden, then Missouri’s governor, awarded Ford part of the $10,000 bounty that had been placed on Jesse James, as well as a pardon for the murder.

By that time, Fellman says, most Missouri Confeder­ates associated with the Democratic Party, of which Crittenden was a member.

“Jesse James was useful to the Democrats when they were fighting the Republicans for power, but once they got the power they wanted economic diversity, and he was a big embarrassment,” Fellman says. “At that point his value was over.”

Frank James turned himself in shortly after his brother’s death, stating that he was tired of running from the law. He was tried, and ultimately acquitted, for robberies and murders in Missouri and Alabama.

David J. Gottlieb, a professor at the University of Kansas School of Law, is working on a book about Frank James’ criminal trial. Seven of the country’s best lawyers, some of whom were former Union soldiers, defended him on a pro bono basis. Many say they packed the jury with former Confederates. The defense did rely on the jury’s Confederate sympathies, Gottlieb says, but they also used the time-honored technique of casting prosecution witnesses in a bad light.


After his acquittal, frank James led a quiet life on the fam­ily farm, occasionally selling tours of the property. Jesse James’ son, Jesse James Jr., became a lawyer. A grandson of Jesse James Jr., James Randal Ross, also entered the profession and was a state court trial judge in Orange County, Calif. He died last year.

Jesse James Jr. wrote a book, Jesse James, My Father, published in 1899. According to the book, the family lived in Kansas City but had to remain in hiding until Jesse James Sr. was killed. To disguise himself, the book says, the elder outlaw walked with a limp and carried a cane. Jesse Jr. was 7 years old when his father died, and he didn’t know his real name until then because the family used assumed names.

The book’s preface suggests that much had been written about Jesse James, and all of it was incorrect. It also recounts the fun times had by father and son and the hardships the family endured following the murder.

Perhaps it was this feeling of unfairness—and a need to financially support his mother and sister—that led Jesse James Jr. to pursue a life of law rather than one of crime. He did criminal defense work and was well-respected in Kan­sas City, Muehlberger says.

Jesse James Jr. later moved to Los Angeles, where he also practiced.

“With his name and family reputation,” Muehlberger says, “he could certainly get a lot of clients.”

Web Extra:

Pleadings from the 1869 civil lawsuit (PDF)




Jesse Woodson James is born in Clay County, Mo., near the site of present-day Kearney


Jesse and his brother Frank steal Daniel Smoote’s horse in an attempt to flee a botched bank robbery


Lawyer Henry McDougal’s age at the time he took on Smoote’s horse theft case against the James brothers


Bounty amount in dollars that is offered for the capture or death of Jesse James


Jesse is shot in his home in St. Joseph, Mo., by Robert Ford and dies the same day


Age of Jesse James at the time of his death on April 3


James Muehlberger—a Kansas City, Mo., lawyer—finds the 100-page, handwritten court record of the lawsuit filed against the James brothers

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