McDougal: Showdown with Jesse James

The following was written in 2007 by Jim Muehlberger, a Kansas City trial lawyer and former prosecutor, for publication in  the February 2010 issue of Wild West magazine (pp. 50-53). Muehlberger found the long-lost lawsuit filed by H.C. McDougal against the James boys in the back of a dusty file cabinet at the Daviess County (MO) court clerk’s office. He also recommends Henry Clay McDougal’s Recollections: 1844-1909.

Showdown with Jesse James

Frontier lawyer Henry Clay McDougal took on the fearsome outlaw in court — and never backed down

by Jim Muehlberger

Among the most dangerous and feared bad men on the Western frontier, Jesse James frightened folks even in states where he had never set foot. Yes, some people most notably the citizens of Northfield, MN, fought back when Jesse and his famous James-Younger Gang associates started to wave their revolvers around. But it usually wasn’t a very good idea to go face to face with Jesse. While robbing banks and trains, he survived at least nine gunfights and probably killed or helped kill as many as 10 people. He was rumored to have killed an equivalent number during his Civil War bushwhacking days.

Although James was never a gunslinger in the mode of say, Wild Bill Hickock, an it has been more than 125 years since his assassination, his name still strikes a chord with folks. The idea of standing exposed on a dusty main street in a showdown with Jesse sounds about as inviting as shaking hands with Bloody Bill Anderson or turning your back on Robert Ford. Who but someone plumb loco would go one-on-one with Jesse in a six-gun exchange? Even Pinkerton detectives weren’t that crazy. But one brave Missouri lawyer sought satisfaction in a more civilized way — he sued Jesse and won. Even more surprising, he lived to tell about it. Barely.

The lawsuit, actually filed against Jesse and older brother Frank, arose from a Dec. 7, 1869, robbery in Gallatin, MO, during which one of the outlaws, most likely Jesse, shot down John Sheets, cashier at the Daviess County Savings Association. As Jesse and another gunman, thought to be Frank, dashed from the bank, Gallatin’s citizens fired on them. Jesse’s horse spooked and bucked as he leaped into the stirrups. He was thrown from the saddle, but his boot remained caught in the stirrup, and the frightened horse began dragging him down the rutted street. Displaying the horsemanship and coolness under fire that would make him a legend, Jesse whipped out a knife, cut the leather stirrup and freed himself. His horse bolted, so he leaped onto the back of his accomplice’s horse.

About a miles outside Gallatin, as the tandem riders were fleeing the posse, they encountered Daniel Smoote, a well-to-do farmer. The outlaws forced Smoote (sometimes recorded as Smoot) at gunpoint to hand over the saddle horse he was riding. The gunmen then galloped off, leaving Smoote standing in the road. The magnificent racehorse left behind in Gallatin was by mid-December identified as the property of “Jesse W. James, living in Clay County.” James family affidavits filed after the crime referred to Jesse’s mare as “Kate” and claimed Jesse had sold the horse the day before the robbery. Kate, one of the finest and fastest horses in Missouri, had been entered in the St. Louis Fair and won several races.

Kate was the first tangible evidence that led to criminal charges against James. In May 1870 a Daviess County grand jury issued a murder indictment against him, and authorities posted a $3,000 reward for his capture or death. With the murder of cashier Sheets at Gallatin, 22-year-old Jesse James had announced his outlaw presence to Missouri and the nation. He would remain a wanted man the rest of his life.


Horse theft was nothing new for Jesse, but farmer Smoote’s reaction was. The latter hired a young and ambitious Gallatin lawyer named Henry Clay McDougal, who had only been practicing law for a year, to sue Jesse and Frank James in January, 1870, for the real value of the horse Jesse had stolen. McDougal also sued for possession of the thoroughbred racehorse Jesse left behind. McDougal, recently married, was a Union Army veteran from Virginia who had moved to Gallatin with his family only three years earlier. He was also a friend of the murdered cashier.

Henry Clay McDougal, Attorney

In Gallatin, McDougal had already proved his courage in connection with another notorious outlaw. After the Civil War, much of the nation suffered a period of unemployment and lawlessness spawning a number of notorious outlaw gangs. The Reno Gang from Indiana began to terrorize the Midwest during this time. About a year after McDougal arrived in Gallatin, on November 17, 1867, outlaws broke open the safe in the Gallatin treasurer’s office and stole $23,618 in cash and bonds. John Reno was identified as one of the robbers. Daviess County Sheriff John Ballinger tracked Reno to a hotel in Indianapolis, where he found the outlaw gambling and enjoying the company of a paid “companion.” Ballinger and Pinkerton detectives captured Reno without a shot.

Ballinger brought Reno back to Gallatin and locked him in the stone-walled county jail. Worried that Reno’s remaining gang members would attempt to break Reno out of jail, or that the infuriated citizens of Gallatin would mob the jail and lynch Reno, Ballinger asked 23-year-old Henry McDougal and five other volunteers to stay in the jail and help watch the prisoners. And so McDougal spent Christmas Day 1867 in jail, guarding a dangerous outlaw.

Two years later, after the latest robbery attempt in Gallatin, McDougal soon discovered he was not Smoote’s first choice for counsel — every one of the other eight lawyers in town had turned down the farmer’s request for legal representation. Young, inexperienced McDougal was the only attorney in the town brave — or foolish — enough to take the case, as to prove the case would effectively hang John Sheets’ murder on Jesse James. This was in an age in which it was said, “To raise your voice or hand against the Jameses’ nefarious operations would cost you your life.”

In fact, soon after McDougal filed the lawsuit, attorney Samuel Harwicke of Liberty, MO, and another man took McDougal around the corner of the old Gallatin courthouse and told him Jesse James had sworn to kill him on sight for seeking possession of the outlaw’s famous racing mare. “As Jesse knew me and I did not know him,” McDougal later wrote, “there was nothing left for me but to take my medicine in absolute silence, and I did.” But Jesse had picked the wrong lawyer to threaten. The threats only prompted McDougal to work with the Pinkerton detectives to track down Jesse. McDougal’s law partner, Marcus A. Low, would meet with Missouri Governor Thomas T. Crittenden 12 years later to offer $10,000 in railroad money for Jesse’s capture, which ultimately led to the outlaw’s murder.

McDougal’s suit against Jesse James didn’t hurt the young lawyer’s popularity in Gallatin. In fact, it made him something of a celebrity. On the first Tuesday in April 1870, McDougal was elected mayor of the town without opposition, a position he would hold for two terms before declining a third. Colonel James McFerran, founder of Gallatin’s Daviess County Savings Association, became his first law partner. And in 1872 McDougal was elected the youngest probate judge in county history. He would thereafter be known as “Judge McDougal.”


Jesse James lawyered up, and the legal fight was on. Frank and Jesse hired Samuel Arbuckle Richardson, the most experienced and successful lawyer in the county, to represent them. Richardson’s knowledge of the law made him one of the most formidable antagonists at the bar to be found anywhere. Men loved or feared him. Richardson’s first move was to ask the judge to squash the service of the complaint, which Clay County Deputy Sheriff John S. Thomason had left at the James family cabin outside Kearney, MO. Richardson argued that Thomason had not established whether a James family member received the lawsuit. The judge granted Richardson’s requested relief, giving the brothers a reprieve. Unless McDougal could somehow serve the complaint on the James boys, the lawsuit was dead in the water.

Meanwhile, in the media storm surrounding Sheets’ murder, Jesse had come to the attention of John Newman Edwards, former Confederal major and founder of The Kansas City Times, who was railing against injustices (perceived and real) being inflicted on former Confederates and encouraging them to jump back into politics. The fiery ad flamboyant Edwards had read about the Gallatin robbery and the notion that Jesse had killed the cashier because he believed the man to be Major Samuel P. Cox, a former Union officer. Cox, who was a resident of Gallatin, had ambushed and killed Bloody Bill Anderson, Jesse’s ruthless Civil War guerrilla leader, in October 1864.

Edwards was fascinated that Jesse had apparently committed murder in the name of the Confederate cause. The publisher arranged a meeting with the outlaw, after which he decided Jesse was a horse he could ride for a distance to further the postwar Southern cause. In June, 1870, Edwards assisted the outlaw in writing the first of Jesse’s many letters to the newspapers. In the letter, Jesse professed his innocence, claimed he was being persecuted for being a former Confederate fighter and offered to turn himself in, if only he would be guaranteed a fair trial. This appeal to the sympathies of former Confederates by waving the Stars and Bars of the Old South was a risky approach — but it worked.

Gallatin attorney H.C. McDougal was just embarking upon his impressive career when he agreed to represent farmer Daniel Smoot in a lawsuit against Jesse James.

Henry McDougal decided to fight fire with fire. As Jesse sought to try the case in the press, McDougal conceived of a novel (at that time) idea to serve Jesse with a complaint: He obtained an order from the Gallatin court that allowed McDougal to inform Jesse of the lawsuit by publishing it in the Gallatin newspaper. So served, the lawsuit was allowed to proceed, and Jesse’s lawyer was ultimately forced to file an answer to Smoote’s accusations. Jesse denied he was in Gallatin on December 7, 1969, and hence denied he had stolen Smoote’s horse.

After two years of legal gunslinging, Jesse found himself outmatched by McDougal’s legal skills and was unable to fight his way out of the lawsuit. When Jesse and Frank refused to appear for trial, the judge ruled in Smoote’s favor on October 20, 1871, awarding him with Jesse James’s prized racehorse. Kate remained an object of considerable interest to visitors over the years, and Smoote raised several fine colts from her. Jesse elected not to appeal but, true to his outlaw nature, twice tried to murder McDougal, narrowly missing each time.


On April 3, 1882, McDougal was in his office with Major Cox when he received a telegraph from law partner Marcus Low: James Gang member Robert Ford had killed Jesse at his home in St. Joseph, MO. In silence McDougal read the wire and then passed to Cox. After Cox finished reading it, McDougal said, “Major, you don’t know what a load that message takes from my mind.” With the fire of war again blazing in his eyes, Cox astonished McDougal by telling him “By Gad, sir, I do know, and I am perhaps the only living man that has known all about this matter for years.” Cox then told McDougal that back in Kentucky he had known the father of Clell Miller, and that in the battle in which he had killed Bill Anderson in Ray County, MO, in 1864, Cox had recognized Clell, only 14 at the time, who was in Anderson’s command and was severely wounded. Cox had driven away one of his men, who was in the act of finishing the boy.

Miller later told Cox that Jesse had ridden to Gallatin in early 1871 with gang members Miller and Dick Liddell to kill McDougal and Cox — McDougal for filing the lawsuit and taking Jesse’s mare, and Cox for killing Bloody Bill Anderson. When Jesse had told Miller the reason for their ride to Gallatin, Miller replied: “Major Cox is my father’s old friend. He saved my life once, and as long as I live, no man shall harm a hair on his head; but I don’t know or care a damn about the other fellow.”

One evening as McDougal and his wife took a stroll, arm in arm, Jesse, Miller an Liddell had waited in ambush behind a hedge. According to Cox, “Her presence alone prevented Jesse from making good his threat in 1871.” It is unknown whether Southern chivalry — or the desire to avoid leaving a witness — prevented Jesse from taking the shot.

In 1883 Governor Crittenden appointed McDougal as a prosecutor in Frank James’ murder trial, billed as the “Trial of the Century.” McDougal also assisted former Sheriff Ballinger in guarding and protecting Liddell, now turned state’s witness, who received almost daily death threats. Liddell told McDougal that in 1882, on Jesse’s last visit to his boyhood home in Kearney, just before he moved to St. Joseph, the outlaw had tried again to kill McDougal.

Liddell said he was with Jesse when he took a shot at McDougal as the lawyer sat in the smoking car of a Rock Island train shortly after leaving the Kearney depot, near the St. Joseph public road crossing. McDougal had been returning to Gallatin from Kansas City. Jesse’s minie ball shattered a window to McDougal’s right, showering glass on the lawyer’s face. McDougal recalled the incident. At the time he told his wife, who was traveling in an adjacent car, that a reckless boy had thrown a stick at the window, in order not to alarm her. While he always suspected the truth, McDougal had never been sure who had fired that shot until Liddell pointed the finger at Jesse.


At the August 1883 Frank James trial in Gallatin, McDougal and the other attorneys chose not to prosecute Frank for Sheets’ murder, as the case against him was weak, and anyway, the late Jesse James had most likely killed the cashier. Instead, Frank was charged with killing a man during the gang’s Winston, MO, train robbery. But the jury acquitted him on September 8. After the trial, McDougal moved to Kansas City. In 1885 he entered into a law partnership with former Governor Crittenden, who had pardoned Bob and Charlie Ford after Jesse’s assassination. Crittenden described McDougal as a “first class lawyer, learned in the black-letter wisdom of the books an as pleasant a social companion as ever a man had or could wish to have.”

In 1895 McDougal became Kansas City’s first counselor, and he successfully represented the city before the U.S. Supreme Court over the acquisition of its water supply and plant, which paved the way for the city’s growth. McDougal died at age 71 on December 17, 1915.

Gallatin in many ways represented both the origin and the terminus of the James boys’ outlaw days. As a result of the 1869 murder of cashier John Sheets, Jesse became a wanted man — for the first time and for the remainder of  his life. Gallatin was also the site of Frank James’ 1883 murder trial, in which he was acquitted. The same lawyer, Henry McDougal, prosecuted both the 1870 civil case over the stolen horse and Frank’s 1883 murder trial.

Although authorities were never able to bring Jesse James to justice, second-year lawyer Henry McDougal was able to recompense one of the outlaw’s many victims. McDougal witnessed a remarkable era in the history of Missouri and America, an era in which the gavel eventually won out over the gun. His life story proved more fascinating than any legend. And in many ways, McDougal is the real hero of the story, for surviving his showdown with Jesse James, even though “the Judge” didn’t fire a single bullet before riding off into the sunset.


Authentic legal documents were rediscovered in August, 2007, by James Muehlberger, shown here with Daviess County Recorder Sue Bird.



John Reno Sentenced to 25 Years

This following account of the 1867 robbery of the treasury of Daviess County, MO, is recorded in the 1882 History of Daviess County (pp. 285-288). John Reno was later sentenced to serve 25 years in prison for this crime:


“On the night of the 17th of November, 1867, a gang of burglars headed by the notorious John Reno, of Indiana, broke into the safe of the treasurer of Daviess county, and made way with what funds they could get, in all some twenty-three thousand dollars. They were pursued, but escaped capture, temporarily. However, they were traced and watched and were at last captured in Indiana and brought back to Daviess county and put in jail. Their names were John Reno, Frank Sparks, Daniel Smith, Silas Smith and Burdet Clifton, and to make assurance doubly sure that they did not escape, a guard of ten men were employed to secure their safety. There were jailed December 15, 1867.


On Saturday, the 16th of November, 1867, John Reno and a confederate arrived in Gallatin for the purpose of robbing the treasury safe, which had some $25,000 in its vaults. The work was to have been done that night, but Reno made the remark that he had traveled so far and was so tired that he would defer the job to the next night, and right there was where he got caught. Had he done the job Saturday night, the start would have been sufficient to have broken the trail, and his confederates to have got over their tremor, but the authorities were after them so quick that the suspected parties gave themselves away and betrayed Reno in their confusion. He and his friend lay in the woods all day Sunday, and that night the work was done. The clerk’s safe was first attached by mistake, and blown open with powder, but on the treasurer’s safe a hinge was wrenched off by a jimmy, and then pried so as to reach the bolts and force them back; then the safe was cleaned out and they left. One of the outside parties suspected was caught with some counterfeit gold coin that was known to have been in the safe for years. This brought him up, and the prospects of being lynched soon opened his mouth, and Reno was followed and caught at Indianapolis, Indiana. A man by the name of Sparks was also captured and brought here, but proved he was not the confederate with Reno and was released. There was proof enough to convict Daniel Smith, Silas Smith, Burdet Clifton, and Clay Able as being accessory to the fact, if not actual participant, but Reno would not give them away, and some heavy lying got them off. The judge took it all out on Reno by a sentence on one, while others were equally guilty before the law, at least for a short term in the same institution, that the assistant prosecutor arose in his place and at once opposed the action of the judge. He was informed that justice was what the people of Daviess county wanted – not revenge. The judge saw his mistake and reduced the sentence to twenty-five years. To mitigate the sentence, $500 had been sent out by Reno’s mother to help pay the loss, and Frank Reno paid $2,000, and they did not expect over a ten years’ sentence. Had the others been put in for from five to ten years, all would have been satisfied. Reno deserved his sentence, but the rest should not have been allowed to escape their punishment entirely. The trial took place January, 1868. The amount of county funds stolen amounted to –

In cash and county warrants — $23,618.19

Stolen money recovered — $2,275

Stolen Warrants recovered – 4,250

Paid by Frank Reno – 2,000

Total loss — $15,093.19

The money and warrants were returned by John Reno after he was captured.

Deliverance Nichols, the deputy county clerk, left the city, and as suspicion fell on him, he was sent after and caught near Milwaukee, Wisconsin. Two twenty dollar compound interest notes were found on him which belonged to the county. He was released on $2,000 bail, but there seems to have been nothing further done in his case. The safe arrival of John Reno in the penitentiary at Jefferson City closed the record of this crime. Captain Ballinger, sheriff, was an active worker in the capture.


After ten years of incarceration John Reno was released. He paid a few thousands and an attempt was made to swindle him out of the money and keep him in prison. The order reducing his term of imprisonment had been placed upon the prison record, and afterward it was effaced. A copy of the order was, also, secured, showing that his sentence had been commuted to ten years. He was released upon $18,000 bail, in case that the commuting of sentence should prove wrong. He was taken out on a writ of habeas corpus and the above bail furnished by his Indiana friends. He was met by his friends in great number and the bail promptly furnished, and to a friend in Jefferson City he wrote that a hundred thousand dollars would have been furnished. His friends claimed that ten years was a full punishment for the Gallatin burglary, and that it was the express company that was trying to prevent his release, and the company was notified that his incarceration again through their instrumentality would be terribly avenged, and that no express company should put him in jail. This was the substance of the letter, which was published at the time in the Jefferson City Tribune. He had, according to the statement of the warden, been an exemplary prisoner during his confinement.

And, last but not least, to Daviess county was the fact that the note given by Frank Reno for $2,000 was never paid. The trouble was that the $500 paid by his mother, the turnover of the warrants and this note, which were intended to mitigate his punishment, did not have the desired effect, but it was certain that a forty years’ sentence, which was only reduced by the appeal of the prosecution of the State, showed the judge was combining justice and revenge. This is Reno’s statement. The note was turned over in 1876 to the county attorney, William M. Rush, to collect but it remains unpaid to this day.