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  • Randy Hopkins

Recovering History: The Freeing of Dick Roland

Updated: Aug 23, 2023

by Randy Hopkins

An affidavit signed by Dick Roland. Courtesy of Ruth Avery Sigler Collection, Oklahoma State University-Tulsa


While most relevant historical and contemporary documents refer to Dick "Rowland,” it is now clear that the correct spelling was “Roland." This is shown by Dick Roland's sworn affidavit of September 16, 1921 (shown above). Apart from direct quotations, the Roland spelling will be used throughout, so as to finally give Dick Roland a “say” in his own history.


On May 31, 1921, Dick Roland, described as a nineteen-year-old negro delivery boy, burst onto the public scene in Tulsa, Oklahoma. The afternoon Tulsa Tribune painted him as attempting to assault Sarah Page, described as a seventeen-year-old white elevator operator and orphan. The public was told that he gave his name as “Diamond Dick” to the Tulsa police when arrested and to have admitted that “he put his hand on her arm in the elevator when she was alone.” Allegations of face scratching, torn clothes, and screams were also mentioned. Roland’s reported arrest and unreported incarceration in the Tulsa County Jail triggered the bloodbath of the Tulsa Race Massacre. [1]

Throughout the ordeal, Roland scarcely put in another public appearance. He was not quoted; the papers published no pictures. There was no immediate trial as the Tribune’s article promised. Like Sarah Page herself, he moved like a phantom through the proceedings. Members of the public filled in the blanks for both with their own preferences and biases. Thanks to records maintained through the years by the Tulsa County Sheriff’s Office, it is now possible to track Roland’s travels through the Tulsa criminal justice system. His journey also throws additional light on a major culprit of the Massacre itself, Tulsa police chief John Gustafson.

The key is a 110-year old log that lists every man, woman, and child confined in the county jail between December 1911 and September 1921. [2] The lack of evident alteration and the consistency of recordation over the ten-year period gives the ancient document much credibility. The leather-bound behemoth lists the prisoners by name, race, and date of imprisonment.

Courtesy of Tulsa County Sheriff’s Office and Randy Hopkins


For each prisoner, the log contains 31 tiny boxes per month, marked with an “x” for every day of confinement. Any release date is noted, along with a circled “x.” Handwritten notations record the reason for release, such as acquitted, transferred to McAlester’s state prison, bonded, and more than a few escapes. For example, the log entry for Tom Owens, aka Roy Belton, who was lynched on August 28, 1920, records that he was “released to mob….”[3]

Courtesy of Tulsa County Sheriff’s Office and Randy Hopkins


Roland shows up as “Rolland, Dick” on the final day of the May 1921 journal. His is the next-to-last name appearing on May 31, consistent with claims by County Sheriff Willard McCullough and City Police Commissioner James Adkison that the prisoner was transferred to County jail around 4:00 p.m. that day. Next to the name is a circled letter “c,” the log’s designation for “colored.” The box for May 31 is marked, but no further explanation is given. [4]

Courtesy of Tulsa County Sheriff’s Office and Casey Roebuck


There is no listing for this prisoner during June or July. [5] This supports claims that Roland was removed from the jail soon after his arrival. The log is not particularly helpful on exactly when Roland was moved. McCullough and later his deputy Barney Cleaver put it around 8 a.m. on June 1 and the log-keeper could have missed a few hours, especially in the chaos. [6]

The log may, however, shed light on where Roland was taken. Roland suddenly reappears there, again as “Rolland, Dick” and again as “colored” on August 3, 1921. [7] Wherever Roland was deposited, the authorities were able to fetch him back. Three destinations have been offered. The most commonly cited is Damie Rowland Ford’s, who told Ruth Avery in 1972 that:

"Sheriff McCullough told me that he had secreted him out from the Tulsa County Jail late Tuesday (May 31) afternoon, and had driven him to stay with some of Sarah Page’s friends in Kansas City, Kansas where she had formerly lived with her ex-husband." [8]

McCullough could not have driven to Kansas City on the 31st and such solicitousness staggers the imagination. McCullough is reported to have told an investigator for the Black Dispatch newspaper that he had served divorce papers on Page several months earlier that painted her as a “notorious character.” [9] If McCullough believed that why would he deliver Roland into the hands of Page’s friends? That Page said something that helped put Roland in jail makes the Kansas City detour even less likely– if that is possible.

Also, if Ford’s version is true, why is Sarah Page listed as one of four witnesses before the Tulsa grand jury that indicted Roland for assault and attempted rape on June 18? [10] If the “hanging” grand jury ignored Page’s pleas on behalf of Roland and indicted him anyway, why did she wait until late September 1921 to send a letter to the Tulsa County Attorney saying she did not want to pursue the case? [11]

Courtesy of Ruth Sigler Avery Collection, Oklahoma State University-Tulsa


A simpler explanation is offered by Randy Krehbiel, who suggests that Roland had been moved to Cleaver’s farm outside town. [12] The farm was a place they could not afford to reveal. Cleaver almost certainly knew of Roland and expressed to Roscoe Dundee, publisher of Oklahoma City’s Black Dispatch, the conviction of his innocence. [13] Of all the versions of what transpired between Roland and Page on the fateful Memorial Day, attempted rape was the least likely, since the occupants of Page’s elevator were visible to outsiders. [14] For Cleaver and McCullough, who were absolutely resolute to prevent losing a prisoner to a lynch mob, the farm offered a safe space for the teenager and an accessible location for them. [15] Keeping him there not only offered protection from a white mob, but anyone from Greenwood who blamed him for the ruin that had fallen upon them. Cleaver could have also communicated with Dave Rowland, patriarch of the family, regarding the safe-keeping.

On June 13, 1921, however, Cleaver told Roscoe Dunjee of Oklahoma City’s Black Dispatch that Roland was in South Omaha, Nebraska and Dunjee printed it boldly. Like Kansas City, it would have been difficult to get him there and to fetch him back, in contrast to Cleaver’s farm. If the deputy was attempting to keep Roland’s enemies from putting two and two together and making for the outskirts of Tulsa, a grand distraction would have been in order. Cleaver appears to have made a similar diversion by telling the Tribune late on June 1 that he didn’t know where his wife was or if she was dead or alive. In 1924, when the heat was off, he suggested that he had already taken “his people” to the farm before the dawn invasion of Greenwood. [16] In short, Cleaver appears to have been prevaricating, but for a good reason, especially if Roland was still farm-bound or nearby.

Wherever Roland was stored, he suddenly reappeared in jail on August 3, 1921, again as “Rolland, Dick.” [17] Why August 3? Besides waiting out the grand jury that finally indicted Roland on June 18, the answer appears to be that John Gustafson was still Tulsa police chief. Gustafson was deeply implicated in the 1920 lynching of Roy Belton. The evidence is also powerful that the Chief was involved in the effort to murder Roland on May 31. [18] Even before the Belton lynching, McCullough viewed Gustafson as unsavory and prophetically warned the incoming Mayor and Commission in May 1920 that a Gustafson “police force would be a menace to the City of Tulsa.” [19] As a result, Gustafson’s police may have been targeting McCullough as much as Roland in their pleas that McCullough take the prisoner out of the impregnable jail and make a run for it. These pleas commenced the very moment custody had been transferred to the Sheriff and continued late into the evening. Cleaver also had his own issues with Gustafson, who forced him out of his long-time police job a few months earlier. [20]

The grand jury that indicted Roland also initiated proceedings for Gustafson’s removal from office on June 25. [21] Gustafson’s trial commenced on July 11, with a guilty verdict late on July 22. The Chief’s motion for a new trial was overruled on July 27 and reported on the 28th. [22] Only after this was Roland returned to jail. Cleaver, and possibly the Sheriff, may have viewed Roland as innocent, but there was nothing they could do about his indictment.

After August 3, the jail log marks a long line of marching x’s next to “Rolland, Dick” for the remainder of Tulsa’s hottest month. The x’s continued to pile up deep into September. while Roland lived in the jail’s so-called “negro dungeon.” [23]

The jail log for "Rolland, Dick" on August 3, 1921. Courtesy of Tulsa County Sheriff’s Office and Casey Roebuck


Events leading to Roland’s eventual freedom commenced on September 12, when state district court judge Redmond S. Cole initiated efforts to clear the county’s backlogged criminal docket. This resulted in the eye-opening discovery that of forty-four pending murder cases, no more than two defendants were housed in the jail. Murder was then a charge for which bail was not allowed. Many others facing lesser charges and not on bail were also absent. Simply releasing prisoners from the county lock-up appears to have been a usual course of action in the 1910s. [24] However, Roland was the most famous prisoner of all time, and the Sheriff could scarcely just let him go, even if he had been so inclined.

Cole’s resulting order placing all the pending cases on a September 28 docket stirred Roland’s lawyers, Washington “Wash” Hudson and Edward “Dynamite Ed” Crossland into action. On September 14, using what turns out to be the correct spelling of “Roland,” they moved to dismiss the grand jury indictment, which Cole granted the next day on technical grounds.

County Attorney Thomas Seaver immediately filed an "information", another process by which criminal charges could be laid. Hudson and Crossland quickly filed a motion to quash, accompanied by the affidavit of “Dick Roland.” [25] The affidavit contains the youth's only known signature and the closest he came to a public appearance. The legitimacy of the signature is bolstered by the jail log, which puts Roland in the county jail on that date, and the fact that it was witnessed by a deputy court clerk. Cole overruled the motion. [26] Dick Roland remained in jail

An affidavit signed by Dick Roland. Courtesy of Ruth Avery Sigler Collection, Oklahoma State University-Tulsa


The matters stood until the September 28 docket call, where both sides were required to announce if they were ready for trial. Seaver issued an attachment summoning Page to appear at the hearing. The next day, the Tulsa Daily World reported in a few sentences buried in a tiny back-page article that the assault charge had been dismissed. A letter from Sarah Page declining to pursue the case was mentioned, though neither Page’s name nor her reasons for so acting were revealed. The jail log confirms the September 28 release date. [27] The Tulsa Tribune, whose May 31 news article had triggered the incineration of Greenwood, did not bother to report Roland’s dismissal. The “Great Forgetting” of Tulsa’s race war was well underway.

The jail log for “Rolland, Dick” on his release date of September 28th, 1921. Courtesy of Tulsa County Sheriff’s office and Casey Roebuck


Dick Roland was now a free man. Ironically, on that same date, the Tulsa Tribune announced that the city-owned Convention Hall would begin a week-long showing of "The Birth of the Nation." Interest in the movie was reported to have been revived by the Ku Klux Klan, which itself had been energized by the Race Massacre. One door of freedom opened, as another door closed. [28]

Courtesy of the Tulsa Daily World


What happened to Roland next is currently evidenced only by Damie Roland Ford’s 1972 interview with Ruth Avery. According to Ford, he stayed in Kansas City where McCullough had deposited him, associated there with Sarah Page, the woman who had a hand in his imprisonment, and then moved to Oregon where he may have succumbed to an industrial accident. [29] As the recent discovery of the County Sheriff’s jail log shows, however, new evidence regarding Roland and Page can emerge at any moment. In fact, it already has. To be continued in the forthcoming article: Recovering History: The Notorious Sarah Page



I would like to express my appreciation to Tulsa County Sheriff’s Office, including Sheriff Vic Regalado, Undersheriff George Brown, Sgt. Mike Moore, head of the Criminal Investigations Division, and Communications Director Casey Roebuck for their courtesies and interest in recovering lost history. As mentioned, Sheriff Regalado was the first to discover Tom Owens/Roy Belton’s log notation. I spent an enjoyable time reviewing with them the treasures of information contained in the jail log. I also thank Sheena Perez at the Oklahoma State University-Tulsa's Special Collections department for her repeated courtesies in making the Ruth Sigler Avery Collection available to this long-distance researcher.


Endnotes: 1. “Nab Negro for Attacking Girl In an Elevator,” Tulsa Tribune, June 1, 1921, 1 (state edition).

2. Prior to June 1918, there were only regular bars separating the men’s and women’s sections of the jail. The women were then moved upstairs. “Police Headquarters Are To Be Improved,” Tulsa Daily World, June 3, 1918, 2. The presence of children is confirmed by the spectacular jailbreak of twelve prisoners from the county lock-up five days before the Race Massacre. The blame for the escape was originally pinned on two prisoners, age 12 and 14, who had been given privileges to roam the jail’s corridor on account of their youth. “Twelve Escape County Jail, Tulsa Tribune, May 26, 1921, 1. Accused robbers and a safecracker later took credit. “Jailer Slept As Prisoners Made Escape,” Tulsa Tribune, May 27, 1921, 1 (”Those two boys didn’t have anything to do with cutting the outer window bars. We just took them along at the last minute.”).

3. The full notation for Tom Owens, first discovered by current Tulsa County Sheriff Vic Regalado, seems to read “released to mob & hurry.” The meaning of the final part, if that’s what says, is as yet undeciphered. Suggestions are welcome. Tulsa County Jail Log, 509.

4.Tulsa County Jail Log, 556-557. The surrender of the doomed Belton occurred under Sheriff James Woolley. The current Sheriff, Willard McCullough, defeated Woolley’s election attempt in large part because of the latter’s weak response. Woolley told the newspapers that he did not risk his life because he was convinced of the prisoner’s guilt. “Call Jury to Find Lynchers,” Tulsa Tribune, August 30, 1920, 1.

5. There is a “Rolland, Noah” also “colored” listed from June 7 to June 23, then released. Dick Roland was indicted for attempted rape on June 18 and was unlikely to have been released five days later. Tulsa County Jail Log, 560-561. A Noah Rolland, oil supply mechanic, is listed in a city directory.

6. “Story of Attack on Woman Denied,” Tulsa Daily World, June 2, 1921, 14. Relying on unnamed sheriff’s deputies, the Tribune reported that Roland was moved at 2:00 a.m. on June 1. “Dick Roland Is Spirited Out of City,” Tulsa Tribune, June 1, 1921, 6. This is peculiar since McCullough and his deputies were then locked tight in the jail, such that it was difficult to access the Sheriff for his signature on a telegram to the governor. Scott Ellsworth, Death in a Promised Land, (Baton Rouge, LA: Louisiana State University Press 1982), 53-54.

Testifying in 1924, Cleaver appeared to support the 8 a.m. transfer. Brief of Plaintiff In Error, William Redfearn vs American Central Insurance Company, No. 15,857, Supreme Court of the State of Oklahoma, 43-46. Cleaver did not mention Roland by name, but said that he, the Sheriff, and “another man went way outside of town by the roadhouse.” The invasion of Greenwood had already broken out around 5 a.m. when “the whistle blew.” Presumably, the trio were not conducting a vice raid in the middle of a race war. Cleaver said he got back in town around 9 a.m. In June 1921, however, Cleaver told the Black Dispatch that Roland was not in the jail when the mob appeared. “Dick Rowland [sic] In South Omaha, No Trace of Girl,” The Black Dispatch, June 17, 1921, 1. Perhaps Roland had been moved within the building to a spot not “in” the jail. In an unpublished manuscript, Roland scholar Steve Gerkin has suggested a move to the third floor as a matter of further concealment. Or, perhaps Cleaver was “jerking the chain” of police chief Gustafson with whom Cleaver then had issues and whose police force had been so energetic and suspicious in urging Roland’s removal from the jail.

7. Tulsa County Jail Log, 574-575. The beginning date of August 3 also serves to verify the credibility of the log. If the notations beginning on that date were some kind of falsities, say to fool later investigators, why not make them in June and July as well? The two-month gap looks odd, if not fishy, until it is linked to the malevolent Gustafson’s stay as police chief as discussed below.

8. “Ruth Avery’s Interviews On The Tulsa Race Riot: Damie Rowland Ford,” Avery Collection. There are three versions of the interview in the Collection. Ruth Sigler Avery appears to have edited the interview in the course of preparing a manuscript for hoped-for publication, eliminating some words and modifying others. The broadest first version is used here.

9. “Loot, Arson, Murder,” The Black Dispatch, June 10, 1921, 1. In fairness to Page, the existing evidence does not support her characterization as a “notorious” character, nor does she appear to have lived with her ex-husband in Kansas City, as will be discussed in a forthcoming essay.

10. Avery Collection, Dick Rowland_07 pdf. The indictment describes Roland as having “violently, forcibly, and feloniously, and against her will, attempt(ed) to ravish, rape, and carnally know her, the said Sarah Page.”

11. “Continue Riot Cases,” Tulsa Daily World, September 29, 1921, 7.

12. Randy Krehbiel, Tulsa 1921, (Norman: University of Oklahoma Press 2019), 59, 77, 82.. Krehbiel relies on the testimony from Cleaver in the 1924 Redfearn litigation regarding a post-invasion visit by McCullough, Cleaver, and “another man” to the outskirts of town. Cleaver also acknowledged having “a place out in the country,” where he had already stashed “some of his people.”

13. Cleaver had been around Greenwood for years and the Roland family was well-known there. Krehbiel, Tulsa 1921, 21-22; John Hope Franklin and John Whittington Franklin, eds., My Life and an Era (Baton Rouge, LA: Louisiana University Press 1997), 198-199. Cleaver lived at 508 North Greenwood and the Roland rooming house was six blocks away at 505 E. Archer. For Cleaver’s belief in innocence, “Dick Rowland In South Omaha, No Trace of Girl,” The Black Dispatch, June 17, 1921, 1.

14. Avery Collection, “DickRowland_04.pdf,” (per Avery, “The elevator was an open type with wire surrounding the lifting platform, the openness making the occupants at all times visible to anyone on the passing three floors. On the street, passersby could see directly in on all occupants”). Tulsa’s Memorial Day parade was passing right in front of the Drexel Building on the morning of the elevator incident. There were lots of people on the street.

15. For McCullough’s deep aversion to losing a prisoner to a mob, Deposition of W. M. McCullough, Stradford v. American Central Ins. Co.; Superior Court of Cook County, No. 370, 274 (1921), 14-16. He testified, “I had talked to my men and told them my ideas of a man who would give up his prisoners, and that I would rather die than give up a prisoner of mine.” When one of his deputies asked what would happen if the mob got “Uncle Bill” and brought him up the stairs ahead of them, he told them, “It don’t make any difference, because I will be dead as hell when they come…” The deputy responded “we will never open them (doors).”

16. “Negro Officer is Heavy Loser in Race Riots,” Tulsa Tribune, June 2, 1921, 3. 17. Tulsa County Jail Log, 574-575.

18. For the role of Gustafson and the Tulsa police in Belton's lynching, see detailed authorities cited in Randy Hopkins, “Racing to the Precipice: Tulsa’s Last Lynching,” The Chronicles of Oklahoma, 98, no. 3 (Fall 2020). For their role in the attempted murder of Dick Roland and the Race Massacre itself, see detailed authorities in Randy Hopkins, “The Plot to Kill ‘Diamond Dick Rowland[sic],’ to be published in The Chronicles of Oklahoma and now online at

19. Then a private citizen, McCullough warned Tulsa’s new mayor and commissioners that:

"Gustafson has all his life been connected with detective agencies and with the underworld, and knew nothing about working with anybody but snitches and crooks, and that he would have no other kind of men on his force, and that such a police force would be a menace to the City of Tulsa."

“Part 1 Attorney Notes of Witness Testimony,” Attorney General Civil Case no. 1062, box 25, record group 1-2, Oklahoma State Archives, Oklahoma Department of Libraries, 2. McCullough told the Attorney General’s office that he did not want to testify in the removal trial because of his “remonstration” over Gustafson’s appointment. By that point, McCullough was tip-toeing around Gustafson.

20. “Statement Barney Cleaver,” Attorney General Civil Case no. 1062, box 25, record group 1–2, Oklahoma State Archives, Oklahoma Department of Libraries, Oklahoma City, OK, 2.

21. “Chief Gustafson Indicted,” Tulsa Tribune, June 25, 1921, 1.

22. “Accused Chief on Trial Alone,” Tulsa Tribune, July 11, 1921, 1; “Jury Convicts Gustafson on Both Counts,” Tulsa Tribune, June 23, 1921, 1; “Deny Gustafson Retrial.” Tulsa Daily World, July 28, 1921, 1.

23. Tulsa County Jail Log, 574-575, 580-581.

24. “44 Murder Cases Load One Docket,” Tulsa Tribune, September 11, 1921, 1; “Court Orders $225,000 in Bonds Seized,” Tulsa Tribune, September 12, 1921, 1; “150 Suspects Forfeit Bonds of $750,000,” Tulsa Tribune, September 13, 1921, 5; “Court Forfeits Criminal Bonds,” Tulsa Daily World, September 13, 1921, 3.

Pursuant to Cole’s order that all defendants report to him on September 12, the Tribune noted that five negroes charged in connection with the race riot appeared. There was no mention of Roland. This nonappearance was likely due to a desire to keep him in a low profile, lest new threats emerge. Judge Cole, who had described the then-called Tulsa Race Riot in the harshest terms, may have agreed to this in advance.

25. Affidavit of Defendant,” Avery Collection, Dick Rowland_06.pdf. According to the district court’s appearance docket, the defendant was present in court on the day of his affidavit. State of Oklahoma vs. Dick Rowland, No. 2239, contained in the Tulsa County Court Clerk’s archives.

26. References to the court proceedings are drawn from court papers in State of Oklahoma vs. Dick Rowland, No. 2239, reproduced in Avery Collection, Dick Rowland_01-10 pdf and contained in the court file in the Tulsa County Clerk’s archives.

27. “Continue Riot Cases,” Tulsa Daily World, September 29, 1921, 7; Tulsa County Jail Log, 580-581. Also, appearance docket in State of Oklahoma vs. Dick Rowland, No. 2239 contained in the Tulsa County Court Clerk’s archives.

28. “Birth of Nation, Revived by Ku Klux, Here Tonight,” Tulsa Tribune, September 28, 1921, 2.

29. “Ruth Avery’s Interviews On The Tulsa Race Riot: Damie Rowland Ford,” Avery Collection.


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