By the 1920s, he had amassed substantial influence in the county when he ordered the contract killings of Osage woman Mollie Kyle's family in a criminal conspiracy to gain control of their headrights.

He was convicted in federal court for ordering the murder of Henry Roan in October 1929, sentenced to life in prison, and released on parole in July 1947.

At age sixteen he began working as a cowboy in West Texas, and by 18 was running cattle on the Kiowa-Comanche reservation in Indian Territory.

[1] Hale was reportedly uneducated, but amassed a fortune through insurance fraud and unfair trade with the native Osage people.

Tom White, the FBI special agent in charge of investigating Hale, wrote in a 1932 memo to FBI Director J. Edgar Hoover: Eventually (Hale) became a millionaire, who dominated local politics and seemingly could not be punished for any of the many crimes ...His method of building up power and prestige was... by means of gifts and favors.

The investigator would later reveal to federal agents that he was hired, not to solve the murders but to manufacture evidence and to coach witnesses to "shape an alibi" for Hale and his accomplices.

Gregg pointed investigators to Al Spencer, Henry Grammer, and Curley Johnson as having more information, but the three men were already dead.

Investigators believed that to orchestrate the killing, Hale had tipped off both Kirby and the store owner as to a potential heist of a shipment of diamonds.

After this revelation, investigators began to believe Hale was possibly murdering witnesses, with some accusations he tampered with Grammer's car brakes and had poisoned Johnson.

[16] Eventually, Burt Lawson, a man serving a prison sentence in McAlester, Oklahoma, came forward to testify he was instructed by Hale and Ernest Burkhart to plant the explosive device in the Smiths' home.

[17] Hale generated additional suspicion when he brought suit to collect a life insurance policy for Henry Roan.

"[19] Agents were also tipped off when they realized the order and methods of the murders appeared to be done in a particular fashion to maximize Mollie's inheritance.

According to David Grann, Hale later turned himself in wearing "a perfectly pressed suit, shoes shined to a gleam, a felt hat, and an overcoat with his diamond-studded Masonic lodge pin fastened to the lapel."

The clouds of seeming guilt may dim thy brother's fameFor Fate may throw suspicion's shade upon the brightest name.

Hale denied the allegations and claimed to be in Fort Worth at a livestock show during the bombing at the Smiths' house and that he had no reason to want Roan dead.

[34] David Grann's 2017 book Killers of the Flower Moon reports Hale as a mastermind of murders with detailed evidence.