It was during this time of working as a cowboy that he would meet most of the members of his future Wild Bunch. Working on the ranches in Oklahoma, Bill Doolin would meet George "Bitter Creek" Newcomb, Charlie Pierce, Bill Power, Dick Broadwell, Bill "Tulsa Jack" Blake, and Emmett Dalton.

Doolin's first brush with the law came in the summer of 1891, while working on the Bar X Bar Ranch. Several of the cowboys decided to celebrate the 4th of July holiday by riding over to Coffeyville, KS and throwing a party. There was a keg of beer there and the law showed up. Kansas was a dry state. When they tried to confiscate the beer there was a shoot-out, and two officers were wounded. From that day on Bill Doolin was on the dodge.

By September of 1891, Bill Doolin was riding with the Dalton Brothers. He participated in the train robberies at Leliaetta, I. T., Red Rock, OT, and Adair, I. T.. Several reasons have been given as to why Bill Doolin did not join the Dalton Gang on their fatal raid on two banks in Coffeyville, KS on Oct. 5, 1892. It has even been rumored that he was the mysterious 6th rider that day. But whether he was the 6th man, or Bob Dalton was jealous of his growing popularity in the gang, or that Bob considered him too much of a "wildcat" and too uncontrollable, one thing is for sure he was a lucky man that day.

With the death of the Daltons in Coffeyville, there were still three members of the Dalton gang at large and they didn't waste time resuming their work. On Oct. 12, 1892, 7 days after the raid, John J. Kloehr of Coffeyville, the citizen who shot 3 of the Daltons, received a letter stating that there was 3 members of the gang left alive and that they were coming to Coffeyville to exact their revenge. Needless to say this put the citizens of Coffeyville in a near state of panic. In the meantime, that same night the train at Caney, KS, eighteen miles west of Coffeyville was robbed by 4 masked men. While never proved, Bill Doolin is credited with both events.

Now on their own, Doolin, Newcomb, and Pierce would have no problem in finding new recruits for their gang. The first to join was Oliver "Ol" Yantis. On Nov. 1, 1892 he would join Doolin and Newcomb and rob the Ford County Bank at Spearville, KS. After the robbery the trio would split up to throw off any pursuing posse. However, marshals were able to track Yantis to his sister's farm near Orlando, OT and on Nov. 30 they surprised him at daybreak and killed him in a brief gun battle.

By the end of 1892, 4 more members had joined the gang, Bill Blake, alias Tulsa Jack, Dan Clifton, alias Dynamite Dick, George "Red Buck" Waightman, and William "Bill" Dalton, brother of the infamous Dalton Boys.

By the spring of 1893 the gang was riding high. Their reputation was growing and their deeds were becoming more bolder. And on March 14, 1893 Bill Doolin and Edith Ellsworth of Ingalls, OT are married in Kingfisher OT Whether Edith knew Bill was an outlaw at the time is not known, but throughout his career as an outlaw she stuck by him, all the time keeping the marriage a secret and meeting him secret

For a "wedding present" the gang robbed the train near Cimarron, KS on June 11, 1893. While being pursued by a posse, Bill Doolin was shot and wounded in the left foot. He would recover from his wound, but it would leave him with a limp and plague him the rest of his life, and would be the contributing factor in his capture years later.

By now, Roy Daugherty (a.k.a. Arkansas Tom Jones) had joined the gang. Unfortunately for him, he had joined the gang just in time for a surprise the marshals had been cooking up for the Wild Bunch. US Deputy Marshals had learned that the Doolin-Dalton gang had been using the town of Ingalls, OT as a hideout the summer of 1893 between raids. On Sept. 1, 1893, two wagons loaded with 13 marshals entered the town of Ingalls. In the fierce battle that ensued, 3 deputy marshals were killed, 2 innocent bystanders were killed and 1 was wounded, 2 of the bandits were wounded, and Arkansas Tom was captured. He was sentenced to 50 years in prison.

In early 1894 the gang was hard at work. Two more members, William F. Raidler (a.k.a. Little Bill) and Richard West (a.k.a. Little Dick) had joined the Wild Bunch. They robbed the Farmers and Citizens Bank in Pawnee, OT on Jan. 23, 1894. On March 13,1894, two men rob the railroad station at Woodwind, OT it was believed to be Bill Doolin and Bill Dalton. The on May 10, 1894, 7 members of Wild Bunch rob the bank in Southwest City, MO. In shoot-out with townsfolk 1 of the bandit was wounded, 1 citizen was killed, and 3 were wounded.

Bill Dalton was not present at the Southwest City robbery, he had left the Wild Bunch and formed his own gang that spring. On May 23, 1894 Jim Wallace, Big Asa Knight, Jim Knight, and George Bennett joined up with Bill Dalton to rob the First National Bank in Longview, TX. Bennett is killed and 1 citizen was killed and 3 were wounded in the attempted getaway. The law trailed Bill Dalton to his hideout near Ardmore, I. T. and surprise and kill him on the morning of June 8, 1894.

Early in 1895 the deputy marshals suspected the gang was hiding out in the Ingalls area. March 3, 1895, Deputies surrounded the cave at the Dunn farm and ordered the bandits to come out. When none appeared, they used dynamite to coax them out. Although the raid did net the law several men wanted for various crimes, none of them were of the Wild Bunch. They had left the day before.

On April 3, 1895 the Wild Bunch would pull it's last job as a gang. They boarded the train at Dover, OT and proceeded to rob it and the passengers. After the robbery the gang would make it way west at a leisure pace unaware that a posse had formed and fast moving in on them. At 2:00 p.m. the posse would catch up with the gang as they were camped near Ames, OT In the gun battle with the deputies Tulsa Jack was killed. The rest of the gang was able to getaway, but they would split up and never re-unite as a gang.

With high rewards on their heads, the gang would scatter. The marshals were now using a new tactic in its efforts to rid the territory of the gang. They had used the reward money and outstanding warrants for cattle rustling to induce the Dunns to give them information as to the movements of the gang. The Dunns had a farm near Ingalls, and were never part of the gang. However, they did give the gang a place to hide out and information about the deputies, as well as fence some of the stolen goods the gang had. On May 1, 1895, while hiding out at the Dunn farm, Bitter Creek Newcomb and Charlie Pierce were shot while they laid asleep in their beds, by Bill, John, and Dal Dunn. They took the bodies to Guthrie and turned them over to the marshal for the $5,000 reward money.

With his buddies dying off one by one, Bill Doolin saw the handwriting on the wall. He had his lawyers get in touch with US Deputy Marshall Nix 3 time that summer and offered to turn himself in if Marshal Nix would promise him a light sentence on robbery. Marshal Nix refuse. The only thing left for Doolin was to leave the territory. He made his way to New Mexico and joined up with Little Dick West. Together they hid out there the rest of the summer of 1895.

On Sept. 6,1895, the law was able to bring another member of the gang to justice. Bill Raidler is seriously wounded and captured by Marshal Bill Tilghman near Pawhuska, OT He stood trail for his part in the Dover robbery and was found guilty, sentenced to 10 years, he was paroled in 1903 and returned to OK

Tiring of New Mexico, Bill would return to Oklahoma to gather his family. By this time Bill and Edith had a son. Together with his family he set out to make a new life for himself. They lived the last part of 1895 near Burden, KS. But the law wasn't finished with Bill Doolin. Deputy Marshal Tilghman learned of Edith Doolin's disappearance from the Ingalls area, and was able to trail her to Burden. However, he was to late, Edith had returned to Oklahoma and a man named "Tom Wilson" had gone to Eureka Springs, AK to seek the healing treatment of the hot spas there to ease the pain of his rheumatism.

Tilghman suspected it was Doolin and proceeded to Eureka Springs were he did indeed find Doolin and was able to get the drop on him and capture him. He returned him to Guthrie and for the first time in his life Bill Doolin was behind bars.

With Bill Doolin behind bars the rest of the gang was being rounded up quick. Red Buck Waightman was killed in gun battle with deputy marshals near Arapaho, OT on March 4, 1896. Dynamite Dick Clifton is arrested on a whiskey charge in Texas. Deputy Marshal Frank Canton brought him back to Oklahoma to face a murder charge, delivering him to the Guthrie jail on June 22. Thanks to the law Bill Doolin and Dynamite Dick were back together.

Then on July 5, 1896, Bill Doolin, Dynamite Dick, and 12 other prisoners escaped from the Guthrie jail. Outside the jail Bill was able to make it back to Lawson, OT were Edith was staying with her folks. Once again they made plans to leave the territory and make a new start somewhere else for their family. Once again the law was chasing him. On Aug. 24, 1896 Bill Doolin was ambushed and killed by Deputy Marshal Heck Thomas's posse.

What happen to the rest of the gang? Dynamite Dick Clifton and Little Dick West were all that was left of the Wild Bunch. They would go on and join up with the Jennings Gang but later leave that gang and eventually be track down and killed by the law. Dynamite Dick Clifton was killed by deputies on Nov. 7 near Chectoah. Little Dick West was killed on April 8, 1898 by Deputy Marshal Heck Thomas's posse.