The marshal departed for Orlando in the last week of August. Tilghman and Colcord were already at Perry, Madsen had gone to Enid, and Chief Deputy Hale was attending a term of district court at Stillwater. Heck Thomas and John Hixon were left in charge at Guthrie to handle any emergencies. Then Nix's office received word that the Doolin gang, enjoying the fruits of the Cimarron robbery, had rendezvoused at Ingalls in Hell's Fringe.
At the time of the battle, Ingalls was a small town of about 150 people, located nine miles east and one mile south of Stillwater, the county seat of Payne County. Ingalls was established a few weeks after the opening of the Unassigned Lands. The small town was named for Senator John J. Ingalls of Kansas and a post office was opened there on January 22, 1890.
The U.S. marshals knew that Ingalls was a hangout for a gang of outlaws known, at times, as the Dalton Gang, the Doolin Gang, or the Starr-Dalton Gang. There were several reasons for the gang liking Ingalls: no local lawmen, three physicians to tend to their injuries, a hotel, two saloons and a gambling house run by Sadie Comley, who also employed three or four girls to entertain the men customers, to pass their time. The town also lay only a few miles west of the Creek Nation and fewer miles north of the Sac and Fox Nation. Another consideration was that Doolin and the gang often hid out at the Bee Dunn place a couple of miles outside of Ingalls.
The gang had originally been formed by three brothers, Bob, Grat and Emmett Dalton. All three had previously been lawmen, Bob and Grat having been deputy U.S. marshals working out of both the Western District of Arkansas and the District of Kansas, while Emmett rode as a posse under his brothers. After having their commissions revoked, Bob and Grat turned to robbing trains and Emmett joined them. With several other outlaws brought into their gang, they were wanted for four robberies: the Wharton train robbery in May 1891, the Lillietta train robbery in September 1891, the Red Rock train robbery in June 1892, and the July 1892 train robbery at Adair.
In October 1892 the gang made the disastrous decision to rob two banks at the same time and picked the town of Coffeyville, Kansas, as its target. Bob, Grat, and Emmett, along with Bill Power and Dick Broadwell, entered Coffeyville but were met with heavy resistance by the townspeople. Bob, Grat, Bill Power, and Dick Broadwell were shot and killed, and Emmett was wounded and captured.
After Coffeyville the gang reorganized with Bill Doolin taking its lead. He was joined by Alfred George "Bitter Creek" Newcomb, also known as the Slaughter's Kid, George "Red Buck" Waightman, Dan "Dynamite Dick" Clifton, William "Tulsa Jack" Blake, Roy "Arkansas Tom" Daugherty, Charley Pierce, and Bill Dalton, the brother of Bob, Grat, and Emmett. In July 1893 they pulled a train robbery a short distance from Cimarron, Kansas, and then found their way back to the Ingalls area.
In July Deputy U.S. Marshals Orrington "Red" Lucas and W.D. "Doc" Roberts made their way into the Ingalls area posing as surveyors. They set up camp south of the Ransom Saloon and frequented the town, looking for signs of the outlaws. They not only saw signs of the outlaws, they saw the outlaws. After heading back to Guthrie, a plan was made to raid the town and arrest the gang.
On August 31, 1893, two wagons left for Ingalls, the first from Stillwater and the second from Guthrie. Both wagons had a driver with several other lawmen concealed in the back covered by canvas. The Stillwater wagon was driven by Dick Speed, the Perkins city marshal and deputy U.S. Marshal. Concealed in the rear were Stillwater constables and deputy U.S. Marshals Tom Hueston and his brother Ham Hueston, deputy U.S. Marshals Henry Keller, George Cox, M.A. Iauson, and H.A. "Hi" Thompson, the Payne County undersheriff and deputy U.S. Marshal. Red Lucas had moved his campsite a few miles southwest of Ingalls. The Stillwater wagon reached the camp around 11 p.m. and prepared for the raid that was planned for midnight. The Guthrie wagon did not show up until daybreak the next morning.
The Guthrie wagon was driven by James Masterson, a Logan County deputy sheriff and deputy U.S. Marshal and the brother of the famous Bat Masterson of Dodge City fame. Concealed in the rear of the wagon were Logan County Sheriff John Hixon, Deputy U.S. Marshals Ike Steel, Steve Burke, Doc Roberts, and Osage Nation police officer and deputy U.S. Marshal Lafe Shadley.
The following morning, Friday, September 1, 1893, Red Lucas drove his wagon into Ingalls to check on the location of the gang. He returned to camp and reported that Bill Doolin, Bill Dalton, Bitter Creek Newcomb, Tulsa Jack, and Dynamite Dick were in Ransom's Saloon, but that he had not spotted Arkansas Tom, Red Buck Waightman, or Charley Pierce. Hixon didn't like the sound of that and sent Iauson to Stillwater with instructions to get more help and return as quickly as possible.
Upon reaching Stillwater, Iauson contacted Chief Deputy U.S. Marshal John Hale and advised him of the situation and the request Hixon had made. Hale, Payne County Sheriff Burdick, and Stillwater City Marshal O.W. Sollers organized a posse of eleven men and headed for Ingalls.
Before the arrival of the reinforcements, the camped lawmen began to move toward Ingalls. The Guthrie wagon skirted Ingalls, coming in from the south on Oak Street and proceeding north of Dr. Pickering's office and home, stopping in a grove of trees. Masterson, Roberts, Steel, Burke, Shadley, and Hale started moving to the west on foot, taking cover behind trees in the area.
The Stillwater wagon, followed by Red Lucas' wagon, came in from the northwest of Ingalls, traveling slowly eastbound on 1st Street. When between Walnut and Ash Streets, the lawmen began dropping out of the wagon and taking cover behind trees and then moving southeast through fields toward the Ransom Saloon. Speed and Lucas kept their wagons moving, turning south on Ash Street and stopping in front of a livery barn just south of 1st Street. Speed stepped down from his wagon and entered the livery, announcing to two men inside that he was a federal officer and for the men to remain in the barn. As he stepped back out the doorway, he spotted a man leading a horse north on Ash Street heading toward the public well. Speed called Dell Simmons over and asked who the horseman was. Simmons points to the man and said, "Why that's Bitter Creek!"
Newcomb observed Simmons pointing and grabbed his rifle out of the saddle scabbard and swung the rifle toward Speed. Speed raised his rifle and fired, sending a bullet into Newcomb's rifle, the bullet ricocheting into the outlaw's right leg near his groin. As Newcomb tried to swing up into the saddle, Speed stepped out into the street to get a clearer shot at the man.
The gunfire was heard by Arkansas Tom, who was on the second floor of the OK Hotel. Grabbing his rifle, he looked out and, seeing Speed raising his rifle toward Bitter Creek, took aim and fired a bullet into Speed's shoulder. Speed tried to take cover behind his wagon, not knowing the shot had come from the Hotel to his east. As he took cover, Arkansas Tom had a clear shot and fired a second shot. This shot hit Speed in the chest, killing him within a matter of minutes.
Newcomb had by now gotten onto his horse, wheeled it around, and raced south on Ash Street, drawing gunfire from the deputies from both the Stillwater and Guthrie wagons. As the lawmen fired on Newcomb, gunfire started from Ransom's Saloon in the direction of the Guthrie deputies, who were moving behind the buildings on the south side of Ash Street toward the Saloon.
While this was happening, Del Simmons, who had taken cover in Vaughn's Saloon across the street from the livery barn, ran out the back toward the hotel and was killed by a shot fired by Arkansas Tom, who probably thought Simmons was a lawman.
As the lawmen from the Guthrie wagon were moving toward the Ransom Saloon from the west, the Stillwater men were moving southward toward the saloon. They noticed a horse standing in front of the saloon, obstructing their sightline. The horse was shot and dropped to the ground dead. Around the same time, N.A. Walker, a citizen from Cushing, ran out of the saloon and was shot in the abdomen by lawmen who mistook him for one of the outlaws.
Shots were now being fired from within the Ransom Saloon, from deputies moving in from the west, and by the second group of lawmen moving in from the northwest. Ransom, the saloon owner, was shot in the leg and took cover in a storage area used to keep ice. Murray, the bartender, opened the front door and raised a rifle toward the lawmen. He was shot in the ribs and arm by three of the marshals.
The gang ran out a south side door of the saloon next door into a livery barn, also owned by the Ransoms, and mounted their horses. Tom Hueston had taken cover behind a pile of lumber between Perry's Dry Goods and Doctor Brigg's residence to cover the saloon's rear door. This position of Hueston gave Arkansas Tom a clear shot; he sighted and fired twice, hitting Hueston in the left side and lower stomach. Hueston fell, still alive but out of action.
As this was happening, Doolin and Clifton rode out the rear door of the livery and headed southwest at a gallop, while Dalton, Waightman, and Blake headed out the livery's front door and south on Ash Street. Hixon, from behind a ditch in front of Doctor Pickering's house, fired on the three going south. His shot hit Dalton's horse in the jaw, causing the horse to stop in his tracks. As Dalton spurred the horse, Shadley, who was behind Doctor Call's office, also fired, hitting the horse in the leg.
Shortly after Shadley had shot the horse out from under Dalton, a shot struck Shadley in the right hip. He was close to Ransom's house but when he asked Mrs. Ransom for help, she refused him entrance and told him to go to Dr. Self's cave, located to the south. The lawman half walked and half crawled to the cave where Dr. Self gave him medical attention.
The outlaws continued out of town at a gallop with Masterson, Hixon, Roberts, Steel, and Burke firing shot after shot at them. Masterson hit Dynamite Dick in the neck, causing him to fall from his horse. He was immediately picked up by another gang member and lifted onto his horse, and they continued out of town. Dalton was also picked up by one of the gang.
As the marshals fired on the outlaws, Doctor Briggs' son Frank ran out into the intersection of 2nd and Oak streets to watch the excitement. He was shot in the shoulder by one of the gang as they returned fire at the marshals. The gang continued and escaped. The lawmen determined that the shots that killed Dick Speed and Dell Simmons, as well as those that wounded Shadley and Hueston, could only have come from the hotel. The hotel was surrounded, and after the Stillwater reinforcements arrived, Dr. Pickering and a preacher talked Arkansas Tom into surrendering.
The wounded Lafe Shadley and Tom Hueston as well as the dead body of Dick Speed were loaded into one of the marshals' wagons for the trip to Stillwater. Arkansas Tom was taken to Stillwater in a separate wagon and jailed in the Payne County jail. Both the wounded lawmen, Tom Hueston and Lafe Shadley, died of their wounds in Stillwater, Hueston on Saturday and Shadley on Sunday.
Results of the Ingalls raid were disastrous. Deputy U.S. Marshal Charles Richard Speed was dead at the scene, as was the Cushing resident, N.A. Walker, and Dell Simmons. Tom Hueston and Lafe Shadley died within days and several others were wounded, and only one of the outlaws was captured, the others escaping. All the outlaws would be brought to justice, but it would take time.
Bill Dalton was killed by deputy U.S. marshals on June 8, 1894, and almost a year later William "Tulsa Jack" Blake died in a gunfight with marshals at Ames on April 4, 1895. George "Bitter Creek" Newcomb and Charlie Pierce were killed on May 3, 1895, at Bill Dunn's ranch southeast of Ingalls. George "Red Buck" Waightman, Bill Doolin, and Dan "Dynamite Dick" Clifton were also killed by lawmen, Waightman on March 5, 1896, Doolin on August 24, 1896, and Clifton on November 7, 1897.
Roy "Arkansas Tom" Daugherty was the only member of the gang to survive into the next century. He was tried in Stillwater and convicted of murder and sent to prison. In 1910 he was paroled and settled in Drumright, Oklahoma, working in a restaurant. By 1916 he had moved to Missouri, and in December was arrested for bank burglary, again being sentenced to prison. Released on November 11, 1921, he appeared to go straight until November 26, 1924, when he and three others pulled a bank robbery in Asbury, Missouri. He again was the target of a police search. On August 16, 1924, officers of the Joplin Police Department tried to arrest Daugherty, but he resisted and was shot and killed by officers.
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