Bob discovered his location in Timber Hills while Grat was away searching in Coffeyville and went ahead to lead the posse in making the arrest himself before Montgomery could escape the territory.
On the night of February 6, 1891, two masked men carrying 44-calibre revolvers held up a Southern Pacific Railroad passenger train near the town of Alila (present day Earlimart, California).
For the four months that Bob and Emmett spent trying to lose Sheriff Kay in the desert, Grat sat in the Tulare County jail in Visalia awaiting his trial.
Though much of the evidence showed that Grat was in Fresno the night of the Alila robbery, including the testimony of several witnesses, the influence of the powerful Southern Pacific Railroad caused him to receive an unfair trial.
Towards the end of the trial, Sheriff Kay, Detective Smith, and District Attorney Power talked to Grat while taking him back to his cell from the court room when Beckenridge was not present.
Witty did have a clue from another deputy that two strange men had been seen hanging around after dark on the open plain near Traver and at the abandoned Overland Stage station at Cross Creek.
Kay suspected that Bob and Emmett might be back in California to free Grat from jail, and took Deputy Witty with him to the Cross Creek station in his buggy.
Maggie Rucker, the woman who once ran the Cross Creek Overland station, was sitting with another girl alone in the front room, silently making dresses.
He had Bill lift the carpet and open the trap door and, instead of Bob, they discovered a man named Riley Dean, a saloon hanger-on from Visalia and Traver.
Angered by the charges against Grat and Bill which he knew to be false, Bob decided that the best way to help his brothers would be to acquire enough money to pay for their bail and defense.
The gang was also assisted by Bob's lover Eugenia Moore, known by her aliases "Tom King" and "Miss Mundays", who acted as their informant, but was also a notorious horse thief and outlaw.
When not preying on the railroads, the gang spent their time digging out large rooms into the steep hills in the cedar brakes on the Northern Canadian River.
When they entered the cell, Bill took out his guitar, sat on a soap box, leaned against the bars of the corridor and began to play a popular song he put his own words to and titled, "You'll Never Miss My Brother Till He's Gone".
They used the bar they had cut out to pry open the grating in the wood room window and, instead of risking going and putting it back, left the broom handle in its place.
He told Kay that Grat's camp was on a steep mountain in the Sierra Nevada, close to the Kings River and about fifteen miles northeast of Sanger, but that they would never find the place.
After pointing out the location of the camp, Middleton left in a hurry and the two posses spent the night on the living room floor of the nearby Elwood ranch.
From their position, Kay and his deputies were fifty yards from Dalton and Dean, who were both discussing their plan to hunt one of Elwood's hogs for Christmas dinner.
Grat rode away from the house, jumped the horse over an old rock fence, and began yelling and firing his revolver in the air so that Dean would know that he had escaped.
The weather conditions during his escape led him to becoming sick with pneumonia, so he stayed near Livingston for several weeks, sleeping in Gray's cupola and watching the surrounding plains with an eyeglass for any sight of a posse.
He then sold the lease to his ranch in San Luis Obispo County, moved his family to his wife's parents in Livingston, California, and left for Kingfisher.
Here, the Santa Fe had found out about the Daltons' plans and attempted to set up a trap for the gang, filling the train with heavily armed officers.
When they arrived, Bob had to think quickly, and decided instead to tie their horses in an alley across from the bank to the west, near the city jail, which offered them little protection.
Meanwhile, Emmett and Bob had entered the First National Bank, covered the officers and two customers, and ordered the cashier, Thomas Ayres, to open the safe with gold and cash.
Outside of a drug store across from the First National, George Cubine was standing with his Winchester aimed at the front door of the bank, awaiting the exit of Bob and Emmett.
Grat ordered the employees to lay on the floor in the back office, and after receiving the signal from Bob, told Powers and Broadwell that it was time to leave.
For a time, Bill Doolin and his partners operated under outlaw Henry Starr (Cherokee), hiding out about 75 miles northeast of Kingfisher, from where they made several raids.
Dalton took part in several robberies with the Wild Bunch, including a gun battle on September 1, 1893, at Ingalls, Oklahoma Territory, where three deputy U. S. marshals were killed.
In it she implied that her father was the one who helped Grat Dalton escape from the Visalia Jail, lending credibility to an earlier claim made by Sheriff Gene Kay of this being true.
Chris Evans and Grat Dalton had become friends while working together in Tulare County during the summer of 1888, at the Grangers Bank of California's wheat warehouses in Tipton and Pixley.
He claimed that Bob, Grat, and Emmett had all made at least two trips to Bill's ranch in California during that time and that at least one of them would show up to his saloon to get a gallon demijohn full of whiskey to bring back to the rest.