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Updated: Jan 3, 2021

Two century-old episodes loom over Oklahoma: the Tulsa Race Massacre and the Osage Reign of Terror. We see these as distinct events– concurrent nightmares that, apart from unfolding in parallel, had little to do with each other. About the furthest anyone seems to have gone, in tracing connections, is to say “there is definitely an intermingling” between the two.

That was David Grann’s take a year ago. He noted that “a private investigator hired by Ernest and Mollie Burkhart,” central figures in Killers of the Flower Moon, had “worked for the Tulsa Police Department and was among the officers who responded to the riot.” But the intermingling is deeper than we seem to recognize.

Because even a limited review of relevant material– historic newspapers and FBI documents online, library books still in circulation– shows several men shaped both the Terror and the Massacre. These men include a disgraced Tulsa Police Chief, on whose watch Greenwood burned; the Oklahoma Attorney General who whitewashed the Massacre; and a leading Pawhuska attorney.

Note: This piece is a sketch, not a finished statement of research findings. But it seems a telling sketch, one warranting further work when pandemic restrictions– on archives, on libraries, on face-to-face interviews– lift.

The Police Chief

A base-level criterion for Tulsa Police Chief candidates: not having been fired from the same force, years before, for “unwarranted actions.” So one would think. But John A. Gustafson was different. The rules most played by, it seems, held little interest.

Randy Krehbiel paints him as a “shady character involved in blackmail and possibly embezzlement, armed robbery, and even murder.” After securing Tulsa’s top law enforcement spot in April 1920, Gustafson still moonlit as a private detective, working “cases that might have been more properly handled by the police.”

The night of the Race Massacre, Gustafson, with Police Commissioner J. M. Adkison and Mayor T. D. Evans, deputized and armed a hostile white mob. At 10:30 P.M., the Chief told Governor James B. A. Robertson “that the authorities in Tulsa could manage the situation.” We know what happened next.

In its aftermath, the state accused Gustafson of several crimes. Some preceded the Massacre. He was implicated in prostitution, car theft rings, and private investigative work for personal gain. The Massacre allegation was that neither he “nor any of the policemen under his supervision and control attempted to intercept or prevent the…crimes” that night.

His attorney T. J. Leahy– more about him later– persuaded Judge Redmond Cole to dismiss the charge regarding Gustafson’s detective agency. And while, at the trial’s end, the Chief was “ousted from office” for his “failure to take proper precautions for the protection of life and property,” his “conviction carrie[d] no criminal conviction with it.” Gustafson escaped punishment.

He later escaped Tulsa as well, moving his private practice to Kansas City. This work took him to Osage County, at the Reign of Terror’s apex.

The Private Investigator

The FBI’s Osage murder files reference Gustafson often. And not for good reasons. The Bureau struggled to determine what, exactly, he was doing in and around Pawhuska, and who was paying him.

One lead was that Leahy, Gustafson’s attorney, and his partner Charles MacDonald– Leahy & MacDonald was a reputable Pawhuska firmhad hired him. Another document identifies “the Administrator of the Estate of W. E. Smith” as his employer. Smith, his wife Rita, and their servant Nettie Brookshire were murdered in a 1923 Fairfax house bombing; Scott Mathis was the administrator of Smith’s estate. Mathis ran with William K. “Bill” Hale, the man behind the bombing and, with his nephews Ernest and Bryan Burkhart, many more Osage killings.

But getting a read on Gustafson entailed more than finding his backers. The Bureau also sought the files he would have amassed working the case. Agents spent the latter part of 1923 attempting, in vain, to secure these documents.

On August 8, for example, Agent Calvin S. Weakley met with Gustafson. The detective said the relevant files were in Tulsa; that he would be in Tulsa the next day; and that he would have the files upon return. On August 10, back from Tulsa, Gustafson explained that the documents were not there, as he had thought, but en route to his Kansas City office. Three months passed. Agent T. F. Weiss went to Kansas City in mid-November. On three separate visits to Gustafson’s office in the downtown Gloyd Building, Weiss encountered only Gustafson’s wife. She informed him that her husband was in Fort Smith, and that the files the Bureau wanted– which agents still had not seen– were in Osage County. So it went.

The mystery surrounding Gustafson drew agents to dark conclusions. Weiss, discussing one informant, stated that because the man was “evading an actual conference with [FBI agents]” and speaking only to Gustafson, he was “at least trying to sell out to the HALE-BURKHART bunch.” Weiss further believed that Gustafson, given his ties to Leahy & MacDonald, was not investigating the killings. He was watching the investigators instead, relaying his findings to Hale.

The Attorney General

No amount of information could, in the end, protect Hale and his nephews, and when their game was up they faced several trials, then jail. David Grann mentions, in passing, that one of Hale’s attorneys “was Sargent Prentiss Freeling, a former Oklahoma attorney general.”

But Freeling, an Oklahoma Hall of Fame member, also led the Race Massacre’s grand jury inquiry. Governor Robertson ordered him “to proceed to Tulsa County forthwith” after it happened, to conduct “a thorough and complete investigation of the rioting.” This investigation, like Gustafon’s in Osage County, was more charade than serious. It helped warp public perception of the event, depicting it as a riot Black Tulsans ignited. Greenwood burned because “inflamed” Black Tulsans, Freeling wrote, were “flurishing [sic] revolvers and guns, and intimidating white people.” They thus “enraged the white population,” prompting them “to pillage and murder.”

FBI Agent T. B. White complained that Freeling and his colleagues later used, “every conceivable means of deceit and unfounded malicious charges” to weaken the case against Hale. “Their object in doing so of course was to thereby defeat justice”– to repeat, in Osage County, what Freeling achieved in Tulsa.

The Man of High Attainments

Hale’s trial set Freeling against T. J. Leahy, Gustafson’s attorney and alleged Osage County employer. Leahy, in some ways, seems principled. Decades before prosecuting Hale, he represented Osage County at Oklahoma’s Constitutional Convention. Historian Joseph B. Thoburn, in 1916, deemed him “a man of high attainments, of profound erudition and practical ability as a lawyer.” A 1924 program, for a convention held “to protect the civil, social, educational and financial rights” of the state’s indigenous peoples, lists him as a Welfare Committee member with the Society of Oklahoma Indians.

But in Pawhuska, Leahy’s “profound erudition” served, among others, guardians, the whites who seized control of Osage wards and wealth. Testifying before Congress in 1924, he conceded his firm was “counsel to a number of guardians.” Fairfax’s Homer Huffaker, with five Osage wards, was one of them.

A 1930 roster of exemplary Oklahomans praised Huffaker as “active in all affairs for civic progress and community betterment.” He served, over the years, as Fairfax mayor and councilman, and as Osage County commissioner. He also helmed the city’s First National Bank. That institution, University of Oklahoma Professor Michael Snyder explains, was “the financial epicenter of the Osage reign of terror.”

The bank’s cashier, Charles E. Ashbrook, was another guardian with five Osage wards. And Hale, Snyder writes, “owned interest in the bank and did most of his banking there.” Huffaker, Ashbrook, Hale, and Scott Mathis– who hired Gustafson– had “so much on each other that neither will talk regarding any of the others,” FBI Agent John K. Wren concluded. “They all have been in various deals together in cheating the Indians out of money.”

Leahy had ties to this cohort both through Huffaker, and through another client: Charles B. Peters, the Tulsa oil baron. Peters bought the First National Bank of Fairfax in 1923, “at the peak of the murders,” and preserved its management structure, with Huffaker president and Ashbrook cashier, after the purchase.

Peters knew powerful men. He was introduced as “an old friend of Senator [Robert L.] Owen’s” when he joined Tulsa’s Chamber of Commerce in June 1921, nine days after the Massacre. The Chamber elected him president the following year. Peters also knew Jesse Livermore, the original “Wolf of Wall Street,” who sat on the board of his Peters Petroleum Company. “Mr. Livermore is said to be one of [its] largest stockholders,” National Petroleum News reported in 1923.

Leahy, for his part, partnered with Peters in several Osage County ventures. Industry publications mention Peters, Leahy, and Peters-Leahy oil firms, all subsidiaries of the Middle States Oil Corporation, all seeking profits in indigenous lands.

There were many ways to make a killing in those days.

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