Dick Gregg

Dick Gregg was a young outlaw whose willingness to speak with T. B. White offered the investigation a rare lead into William K. Hale’s plans for the Smiths. Gregg described a meeting at Hale’s pasture where Hale sought to hire the Al Spencer Gang to kill Bill Smith and his wife. Gregg said he refused, but the value of his account was shadowed by the risks of his own position and the loss of its only named corroborating witness.

Identity and Background

At twenty-three, Gregg was serving a ten-year sentence for robbery in a Kansas penitentiary. He had been a member of the Al Spencer Gang and was known as a stickup man, placing him among the outlaws T. B. White turned to when the investigation stalled. White believed that prejudiced and corrupt white citizens would not implicate one of their own in the killing of American Indians. Reports suggested that outlaws in the Osage Hills knew something about the murders; their criminal records, White reasoned, might give investigators leverage that community respectability could not.

Gregg’s appearance and character seemed to White more complicated than his record. White later recalled him as a small, fair-complexioned young man, about five feet six inches tall and 125 pounds, with blue eyes and light brown hair. A prosecutor, by contrast, considered him cold, calculating, and capable of murder. White did not dismiss that danger, but thought Gregg might have gone far with proper training. The contrast mattered to White’s assessment of the witness: a hardened criminal could still, in this instance, refuse a killing-for-hire scheme.

From Reluctance to Cooperation

Gregg had previously told Agent Burger that he knew something about the murders, while insisting he could not betray a confidence. Burger found him frustratingly guarded. Comstock, who knew Gregg’s father and provided legal counsel to the family, helped persuade him to cooperate with the Bureau, despite J. Edgar Hoover’s continuing distrust of Comstock.

Gregg had reason to fear Hale. He warned that if word of his disclosures got out, his life would not be worth anything. He nevertheless agreed to tell T. B. White and other agents what he knew, hoping that cooperation might reduce his robbery sentence. His testimony thus came from a precarious bargain: it might help expose a murder plot, but it could also place a prisoner with powerful enemies in danger.

The Pasture Meeting and the Smiths

Gregg dated the meeting to the summer of 1922. According to his account, Al Spencer told him that Hale wanted to meet the gang. Spencer, Gregg, and several associates went to one of Hale’s pastures near Fairfax, Oklahoma. Hale rode up through the tall prairie grass; the group gathered beside a creek and shared whiskey. Hale then drew Spencer aside for a private conversation. After the meeting broke up, Spencer told the others what Hale had proposed.

Gregg said Hale had offered at least $2,000 to kill a couple: an old man and his blanket, meaning an Indian woman. When Spencer asked who Hale wanted dead, Hale named Bill Smith and his wife. Spencer refused, saying he would not kill a woman for money. Gregg said he agreed with Spencer. In White’s judgment, Gregg was being truthful, and refusing the job suggested an outlaw with some honor. The story was the clearest indication yet that Hale had ordered the murders, but it remained an account of a conversation Gregg had not personally heard: Spencer was the one who had spoken privately with Hale and later relayed Hale’s words.

Evidentiary Limits and Investigative Significance

Gregg’s disclosure was important but legally vulnerable. He was a convicted robber who hoped to shorten his sentence, giving the defense reason to challenge his motives. More seriously, Spencer—the person who could have corroborated the account—had been killed by a posse of lawmen. Gregg could describe the meeting and report what Spencer had told him afterward, but the investigation had lost the witness best placed to verify Hale’s offer directly.

Gregg also pointed investigators toward Curley Johnson, saying Johnson knew about the Smith house bombing and would talk under pressure. That lead ended in another dead end: Johnson had died suddenly less than a year earlier, with poisoned alcohol given as the reported cause. Gregg’s cooperation therefore opened investigative paths without resolving them. His testimony strengthened the case’s picture of Hale’s reach into outlaw circles, while the deaths of Spencer and Johnson exposed how few independent witnesses remained to make that picture courtroom-proof.

Gregg’s place in the investigation also reflects the larger difficulty of pursuing crimes against the Osage. Private detectives had been hired to investigate Osage deaths, including by Anna Brown’s estate, while the federal government subjected many Osage to guardianship and control over their spending. In 1921, restricted Osage trust beneficiaries could withdraw only limited sums each year, even for needs such as education or a child’s hospital care. Gregg was not presented as part of that guardianship system; rather, his account entered an investigation unfolding amid a broader structure in which Osage families faced both violence and imposed limits on their own resources. White’s turn to outlaws was a tactical response to the failure of more respectable local channels to produce witnesses against Hale.