Although Bob, like several of his brothers, is known as an outlaw, he was a lawman in 1888 when he shot bothersome Charlie Montgomery in the line of duty.

Bob Dalton didn’t take kindly to anybody fooling around with his girlfriend, Minnie. And that, ac- cording to one of the West’s durable stories of lust, betrayal and vengeance, was why swaggering Charlie Montgomery ended up permanently dead of lead poisoning.

Minnie was said to be Bob’s gal up around Coffeyville, Kan. She might have been kin, too—a first cousin, according to one version; mother Adeline Dalton’s “adopted niece,” according to another. In any case, Bob and Minnie, who was described in one fanciful book as “sprightly, saucy, thoughtless,” were apparently indulging in the occasional roll in the hay. Legend tells us that Minnie became intrigued with big, engaging Charlie and took up with him, too. Bob’s manhood had been affronted and he wanted revenge in a bad way. Killing the man figured to do the trick.

The classic tale is as unlikely as the one about Bob Dalton once playing William Tell by shooting an apple off the head of a terrified boy. But there really was a Charles Montgomery, and his association with Dalton was indeed a deadly affair. Neither fellow was particularly likable, although their meeting occurred before Bob and some of his brothers began robbing banks and trains and shooting people who stood in their way. At the time, August 1888, Bob and his brother Grat were on the right side of the law, following at least for a little while in the footsteps of their admirable brother Frank, who had been killed the year before in the line of duty down in the brakes of the Arkansas.

As for Montgomery, he was a hoodlum of the same stamp as the Daltons later turned out to be, only, it would appear, a lot less capable.

But back to Minnie for a moment or two. She, according to the legend, was sharing her favors with big Charlie (sometimes seen as Charley) while honest Bob was away being a lawman. Bob’s parents might have even been the ones to spill the beans on Minnie. In any case, Bob supposedly took elder brother Grat with him to search Charlie’s quarters and found a lady’s red-silk handkerchief that Bob had once given his true love. The distressed Dalton, one account says, “nearly hit the fly-specked ceiling.” He perceived Minnie’s hanky-panky to be a monstrous wrong. When she found out how irritated Bob was, Minnie collected her new man, Charlie, and suggested they would be safer in Kansas City. The lovebirds, the story goes, departed Coffeyville by train while Bob shot holes in the passenger car.

Somewhat later, Montgomery returned to Coffeyville to retrieve some belongings, and that turned out to be a serious mistake. There are several versions of what happened next, but most of them suggest that Bob promptly shot down Charlie from behind. In his 1963 book The Dalton Gang: End of an Outlaw Era, the ever-inventive Homer Preece wrote that “as part of what seems to have been a calculated frame-up, Minnie’s bridegroom had been told that her ex-lover was miles away from Coffeyville and Indian Territory.” His rival having expired, Bob then announced that he had killed Montgomery in the line of duty. Bob declared that the shooting was justified, his rival being a lowdown horse thief and Bob a posseman for his brother Grat, who was then serving as a deputy U.S. marshal. The local undertaker, goes the same tale, even “agreed to charge Charlie’s laying-away to the Federal court at Wichita,” although in fact that was the sort of expense federal courts simply did not pay for in those days.

Suffice it to say that Preece and so many others probably got only one thing right in telling this Dalton tale— that Charlie Montgomery was in fact a nasty piece of work who ended up dead at the ugly end of a Dalton bullet. The rest is invention, pure moonshine: Bob didn’t ambush and shoot down Montgomery out of offended macho pride, and the seductive Minnie was almost surely a delicious invention (and almost certainly not a cousin). No proof exists that she knew Bob Dalton from Adam’s off ox or, for that matter, that she existed at all.

Montgomery himself did exist and did depart this earth most violently on August 15, 1888. What really happened to Montgomery, and Robert Dalton’s involvement in his demise, became clear during testimony before the U.S. commissioner at Fort Smith late in 1888 and early the next year. Bob was named as the defendant in this proceeding, along with his brother Grat and possemen A.J. Landers and Jeff Greggs (or Griggs). They were present at the hearing, charged with murder and represented by two lawyers, William Millelle and E. Boudinot. In the leisurely fashion of the day, the commissioner’s hearing was repeatedly continued, probably as more witnesses were located and called to testify.

Montgomery seems to have been a perpetual pest, plaguing the honest men in northeastern Indian Territory (present-day Oklahoma). According to evidence given at a U.S. magistrate’s hearing after his death, he was a penny ante criminal who told people he was a deputy marshal working out of the federal district court. When he was asked to produce some evidence of that employment, he had nothing to show. In later years, Littleton Dalton, Bob’s brother, described Montgomery as “a no-good scamp, a bootlegger, gambler, road agent and pimp.”

In 1888, Montgomery was a special irritant around Bartlesville, a tiny settlement in the Cherokee Nation, lying north of modern-day Tulsa and not far south of the Kansas line. Bartlesville was about a day’s ride from Coffeyville, where just four years later the outlaw Daltons would meet their bloody Waterloo. The Indian Territory town didn’t have much going for it except for a flour mill and a general store owned by Jacob (“Jake”) Bartles, a tough, resourceful man who had married a Delaware Indian princess and settled in the Turkey Creek country in 1874. His store carried everything a settler could wish for, from groceries and clothing to plows and Studebaker wagons, and business was good. In time, he parlayed his boundless energy and sound business sense into large herds of cattle, hundreds of acres of wheat, a rooming house, a post office (he was the postmaster), a livery stable, an ice house and a blacksmith shop. He even built housing for his workers.

Bartles didn’t much like Montgomery, whom he rightly suspected of stealing merchandise. Bartles learned from Jim Long, one of his employees, that Montgomery had approached Long with a proposition to “steal two mares and rob my store,” as Bartles put it at the U.S. commissioner’s hearing. Long confirmed that Montgomery had not only stolen from Bartles’ store (close to $300 worth of goods) and proposed more of the same but also said, “We can down Jake Bartles for his money.” Montgomery also suggested to Long that they go into Osage County to peddle whiskey.

At the time of his death, Montgomery was carrying two revolvers that he had “borrowed.” The Coffeyville Journal later reported: “[Montgomery] had been playing some unwarranted games since his advent there…about a month ago he came to Coffeyville and represented himself as a U.S. Marshal, and had to be arrested and disarmed. He was suspected of…running off horses…and various petty crimes….Lately he had appropriated two revolvers that did not belong to him, and had secured a horse that was not his own.”

After hearing from Long about Montgomery’s misdeeds, Bartles summoned the law. The posse that showed up consisted of Bob and Grat Dalton, Sheriff Ed Sanders, an Indian policeman named Wiley, possemen William Rogers (from whom Montgomery had appropriated one of his six-shooters) and two others (Newt Harris and James Couch). These lawmen set up an ambush to capture their quarry as he met Long for further conspiracy, but Montgomery did not appear.

Several days of fruitless searching followed, until at last Bob Dalton got word that Montgomery would be at a house occupied by one Junius Brown and his family. Bob rounded up possemen Jeff Greggs and Al Landers and rode out to the Brown place, where they dismounted and approached the house on foot. Bob (at the commissioner’s hearing) explained what happened next: “I went to south side of house and Griggs and Landers went to northwest corner….Just as I stepped over the yard fence, the dog barked and I seen Landers dodge down behind the fence and just immediately I heard a gun fire.”

Montgomery had fired at Landers and Greggs, and now Montgomery ran around the side of the house. Bob heard Landers shout “Stop! Throw up your hands!” and at this another shot rang out, although Bob could not know who had fired. Bob ran around the house in the other direction, and met Montgomery head-on, running around the other side of the building, six-shooter in hand. According to Bob, he challenged Montgomery, getting no further than, “Stop, Charlie,” when his quarry fired point-blank into his face.

Miraculously, Montgomery missed, although the range was only about 8 feet, so close that the muzzle blast from his revolver scorched Bob’s cheek. Bob did not miss. A round from his shotgun knocked the outlaw down, and as the smoke cleared, Bob saw Montgomery on his hands and knees. Shot in the stomach, Montgomery still tried to fire one of his six-shooters, so Bob snatched the weapon from his hand. Montgomery then reached for his other revolver, but Landers arrived in time to grab that one.

Bob remembered hearing two shots from where his possemen were, and three from Montgomery. He testified that one of Montgomery’s six-shooters had four chambers fired.

Bob told the magistrate that he went after Montgomery as “posse for my brother, who was a deputy U.S. marshal of this district.” He admitted that neither he nor brother Grat had a warrant for Montgomery, but were after him for “stealing the pistols and stealing a horse.” Bob added, “When we heard he was going to leave the country, we concluded it was best to arrest him before he would be gone.” And Bob was also moved to deny on cross-examination that there was a conspiracy to kill Montgomery. Grat Dalton acknowledged that Bob had been his posseman, and also denied any sort of conspiracy to kill Montgomery. He confirmed that four chambers had been fired from one of the handguns taken from the dead man.

Greggs had been with Landers at the fence some 15 feet from the house when Brown’s dog gave the alarm. Montgomery, sitting in a chair with his back against a post, leaped to his feet, pulled out a revolver and blazed away. The first shot tore through Greggs’ hat brim and knocked the hat from his head. Montgomery took cover around the corner of the house and fired again, and his second round put a hole in the crown of the hat as it lay on the ground. About that time, Landers shouted at Montgomery to throw up his hands, but the answer was still another gunshot, a round that struck a fence post about four feet from Landers. Greggs and Landers returned fire almost together, and then Montgomery turned around the corner of the house out of their sight. “Just as he got out of my sight, there was a pistol and a shotgun fired,” Greggs said later. “The pistol fired just a little before the shotgun.” Greggs also denied any conspiracy to kill Montgomery, and in fact said flatly that Bob had instructed him not to fire at Montgomery “if he started to run, because he had no warrant for him and he did not want to kill him.”

Landers confirmed the stories told by both Bob Dalton and Greggs. He added that he heard Montgomery say “Damn you” before shooting at him and Greggs and that one of Montgomery’s bullets tore some skin from his ear. Bob Dalton, according to Landers, had called out, “Hold up Charlie!” to no effect. Later, Landers saw “two or three grains of powder” sticking to Bob’s right cheekbone, and Bob complained that his face burned.

Apparently, somebody alleged that Montgomery had been assassinated at Jake Bartles’ request, because, at the hearing, Bartles admitted to being suspicious of Montgomery but denied ever offering “any money to defendants to arrest or kill Deceased.” Brown’s wife, Phebe, should have been a key witness, for she was at home when the fight occurred, but she turned out to be confused and unclear about the events outside her home. She testified to hearing six or seven shots, but she did not know who had fired them. She said she saw Montgomery fall, and said that he had been sitting under a brush shed, then walked across it and was shot “in front of the door,” which sounds as if it might be at odds with Bob Dalton’s version of the killing. She then added that she did not know whether or not Montgomery had fired a weapon. “I did not see him,” she admitted. “I was paying no attention, my baby was crying and I was trying to quiet it. And it was done so quick that I did not know what was done….I was so excited that I could not tell anything about the occurrence.”

Junius Brown was in the barn when the shooting started, but he said he heard seven or eight shots fired “just so fast you could count.” He got to the stable door in time to see Montgomery fall “nearly in front of the house door, not quite in front of the door.” Brown added that Montgomery had been staying “on and off” at Brown’s place for two days.

Montgomery had shown Brown a letter he said had come from the Daltons “to arrest a man,” although Brown did not read the letter. Montgomery had also complained to him that the Daltons were after him, and that they intended to kill him, having overheard one of them say as much. Brown added one other interesting note. After the shootout, Dalton and Landers had asked him to examine one of Montgomery’s sixshooters, and he had found “four loads were out of it” but could not say whether it had been recently fired.

Another witness, one William Ellington, also confirmed that four chambers of Montgomery’s six-shooter were empty. And Ellington, who went to Brown’s farm after the fight to pick up Montgomery’s remains, added that not long before the shooting, Montgomery had talked of his troubles and had said that he “wanted to go down to Jake Bartles and kill him and take his best horse and leave.” Surrendering was impossible, Montgomery had told Ellington, because Bartles had offered the Daltons “some $265 to $300” to kill him.

A witness named Griggs—no apparent relation to the posseman—said that Montgomery had worked hard for him for six or seven months before quitting and going off somewhere. Later, Griggs said, both Montgomery and Bob Dalton told him that the badge-wearing Daltons had asked Montgomery to be an informer for them. Griggs also said that Montgomery had knowledge of an incident 12 years earlier in which Bartles had hired someone to kill “some boys,” and that Bartles wanted Montgomery removed “and he did not care how.” Although Griggs contended that Bartles had offered $100 to get Montgomery out of the way, Bartles claimed that he had only been willing to pay $50 for the conviction of Montgomery.

In a sworn statement, a man named A.P. Lyman said that Montgomery had come to his home on August 11, four days before the shootout, complaining that a man named Jim Frye “had given him away,” that Frye, Jake Bartles and the Dalton boys were after him, and that he wanted to “kill the whole damned ring.” Lyman was concerned enough to go into Coffeyville the next day to find out if Montgomery had committed some crime. In town, Lyman met an old man named Kerr, who said that Montgomery hadn’t done a thing, adding, “He don’t want to kill anybody but Jake Bartles; he is at the bottom of the whole damned thing.” Clearly, Kerr hated Bartles, too, because, according to Lyman’s statement, Kerr had said that he would give Montgomery money to leave the country if Montgomery killed Bartles.

Trying to make complete sense of all the testimony is no easy task. Clearly, though, the shooting of Charlie Montgomery had nothing to do with passion or a delectable woman named Minnie. In short, Bartles and Montgomery couldn’t stand each other, and Bob Dalton, a posseman for his brother Deputy Marshal Grat Dalton, got in the middle of it. In view of the unanimity of the lawmen’s testimony about what happened at Brown’s farm, and considering the disreputable reputation of the dead man, it is not surprising that the case ended before the magistrate and went no further.

Even if Bob had been entirely justified in killing Montgomery, the gut shooting might have scarred his heart. Littleton Dalton, for one, said that his brother Bob took this taking of another man’s life hard. “Bob went bad,” Littleton said. “He drank more and became more restless all the time. He didn’t seem to care what became of him. I believe he was the final cause of Mason [Bill] and Grat going bad.” Well, maybe. But the Daltons weren’t the first badge wearers to jump to the other side of the law, and if Bob really did so abhor bloodshed, turning to a life of crime wasn’t likely to shield him from it. It wasn’t as if Charlie Montgomery had been a noble fellow who had never done wrong…just the opposite. In the casual common law of the West, Charlie just needed killing.


Robert Barr Smith, a former U.S. Army colonel who is now a University of Oklahoma law professor, has contributed many articles to Wild West Magazine and has written several books, including Daltons! The Raid on Coffeyville, Kansas. Also suggested for further reading: The Dalton Gang Story,by Nancy B. Samuelson;The Dalton Gang: End of an Outlaw Era,by Harold Preece; Dalton Gang Days, by Frank Latta; and West of Hell’s Fringe: Crime, Criminals, and the Federal Peace Officer in Oklahoma Territory, 1889-1907, by Glenn Shirley.

Originally published in the April 2007 issue of Wild West. To subscribe, click here