Gentner Drummond, David Ostrowe
Oklahoma Attorney General Gentner Drummond, left, sent a letter to former Secretary of Digital Transformation David Ostrowe on Wednesday, Feb. 1, 2023. (NonDoc)

(Update: David Ostrowe dismissed the lawsuit referenced below Friday, Feb. 10, 2023, days after the publication of this article, which remains in its original form.)

As former Secretary of Digital Transformation David Ostrowe determines whether to serve his lawsuit against the state of Oklahoma, new Attorney General Gentner Drummond sent Ostrowe a letter today apologizing for how former Attorney General Mike Hunter’s administration handled Ostrowe’s controversial 2020 grand jury indictment, which Hunter dismissed when he suddenly resigned from office in May 2021.

“Upon review and examination of the facts surrounding your case, I have concluded that the prior administration of Attorney General Michael J. Hunter failed to adhere to necessary protocols to avoid any appearance of impropriety,” Drummond wrote in his letter (embedded below). “Specifically, former Attorney General Hunter should have disqualified himself from any involvement in the investigation of potential or alleged wrongdoing by you.”

Mike Hunter resigned as Oklahoma attorney general Wednesday, May 26, 2021. (Michael Duncan)

It’s unclear specifically why Drummond believes Hunter should have disqualified himself from the Ostrowe case, but Ostrowe has alleged that Hunter “weaponized” the state’s top law enforcement office by conducting “outcome oriented” investigations. In his case, Ostrowe believes his efforts to change practices and structure at the Oklahoma Tax Commission spurred a politicized investigation aimed at indicting him and discrediting Gov. Kevin Stitt, with whom Hunter had clashed on various matters.

In a December 2021 tort notice letter to the Tax Commission and the Attorney General’s Office, Ostrowe’s attorney wrote that Mike Hunter’s AG Office “became a place where political favorites went to get revenge or get a favor, and not where victims felt safe to get justice.” (In September 2022, Ostrowe filed a lawsuit against the Tax Commission, its three commissioners circa 2020 and Hunter, although he has not formally served the defendants.)

Drummond’s criticism of Hunter is longstanding, having narrowly lost to him in the 2018 Republican primary for attorney general. After Hunter resigned, Stitt chose John O’Connor over Drummond as his attorney general appointee, but Drummond ran for the office in 2022 and narrowly defeated O’Connor in the primary.

“Under my leadership, I assure you it is the mission of this office to hold accountable individuals who violate the law, while also preserving the integrity of our investigative functions and respecting the rights of the individuals being investigated,” Drummond wrote to Ostrowe on Wednesday. “I believe fundamental fairness and honesty should be preserved, protected, and facilitated for the benefit of all citizens of this state.”

Ostrowe case offers rare glimpse at grand jury process

David Ostrowe
Then-Oklahoma Secretary of Digital Transformation David Ostrowe, left, speaks to media with his attorney, Matthew Felty, at the State Capitol on Wednesday, June 2, 2021. (Tres Savage)

David Ostrowe believes his December 2020 indictment by the state’s multi-county grand jury was fundamentally unfair and dishonest. The MCGJ is Oklahoma’s most powerful investigatory body. It meets for 18-month terms, and dozens of law enforcement agencies use it to compel testimony, request search warrants and seek indictments on major crimes, including political corruption.

The multi-county grand jury that indicted Ostrowe was the state’s 18th MCGJ, which also heard testimony regarding a litany of high-profile matters, including the indictment of Rep. Terry O’Donnell (R-Catoosa), the investigation into former University of Oklahoma President David Boren and the Epic Youth Services case. However, hearings before Oklahoma’s 18th multi-county grand jury dwindled in 2021 after presiding Judge Tim Henderson resigned amid a sex scandal. Two months later, Hunter resigned as well and dismissed the Ostrowe case.

The grand jury had indicted Ostrowe on Dec. 17, 2020, after hearing two rounds of testimony from only one indirect witness. Ostrowe was charged with attempted bribery related to conversations regarding former Sen. Jason Smalley’s delinquent business taxes.

Smalley had contacted the Legislature’s budget chairmen — Sen. Roger Thompson (R-Okemah) and Rep. Kevin Wallace (R-Wellston) — about the matter, and Thompson subsequently contacted Ostrowe, whose service in Stitt’s cabinet included being a liaison to the Oklahoma Tax Commission.

When the multi-county grand jury heard testimony about the matter in November and December 2020, only Attorney General’s Office investigator Thomas Helm took the stand. Questioned by then-MCGJ chief Joy Thorp, Helm relayed details of his conversations with Thompson, Smalley, members of the Oklahoma Tax Commission and Ostrowe, some of which had occurred with Thorp in the room at the same time.

By comparison, former Oklahoma County District Attorney David Prater hauled 27 state employees, elected officials and others in front of grand juries to form the basis for his December 2021 indictment of O’Donnell, a high-ranking member of the Oklahoma Legislature.

But in the Ostrowe case, grand jurors heard only from Helm, a law enforcement official with no first-hand knowledge of the situation being investigated. That point was emphasized when a juror asked Helm about the nature of Ostrowe’s business background and Helm said he did not know, even though Ostrowe’s LinkedIn account openly states that he is the CEO of a venture capital fund that invests in fast food restaurants.

After Hunter dismissed the indictment against Ostrowe in May 2021, NonDoc reviewed transcripts of the case’s grand jury testimony, some of which focused on Ostrowe’s text messages with then-tax commissioners Charlie Prater, Steve Burrage and Clark Jolley.

“Hopefully Steve and Charlie understand that this is a Thompson personal request,” Ostrowe wrote to Jolley. “Might make the budget go easier.”

Jolley replied: “I’m sure they’ll do the standard relief. Is he wanting more than what average taxpayers are getting?”

Ostrowe replied: “I think he wants zero plus the tax due.”

Thompson has previously stated that he never threatened reduced appropriations and did not instruct Ostrowe to seek a specific outcome on the tax matter for Smalley, who ultimately paid his taxes and penalties as assessed by OTC.



Prater outlines investigation as indicted O’Donnell blames ‘woke left,’ hints at Hunter history by Tres Savage

But neither Smalley, Thompson, Jolley, Prater nor Burrage ever answered questions in front of the grand jurors, who instead only heard from Helm. To conclude his testimony, Helm referenced an Ostrowe proposal that could have increased the number of state tax commissioners while decreasing their $147,000 salaries. In conversations with legislators, Ostrowe had discussed potentially becoming an appointed tax commissioner himself.

The foreperson of the grand jury asked Helm why Ostrowe might want to be a tax commissioner.

“I don’t know. Although, it maybe makes him more marketable for a future endeavor, would be my guess,” Helm said. “You know, if you’re looking at a resume and attempting, as you said, to try to spring forward and build power, it would be a feather in the cap or a line on a resume that would help him.”

Thorp, whose job was to present the state’s case and ask questions of Helm during his testimony, asked about the Tax Commission’s role in handling business taxes.

“As a business owner, would that be something that [Ostrowe] would be interested in, knowing that he’s a member of the Young President’s Association or organization?” Thorp asked.

Helm replied: “Certainly.”

“So he could potentially affect all of Oklahoma through being a tax commissioner?” Thorp asked.

Helm said, “That’s correct.”

Although Thorp left the AG’s Office in 2022 to become first assistant district attorney in Rogers County, Drummond’s office confirmed Wednesday that Helm was still employed as an Attorney General’s Office investigator.

That information landed poorly with Ostrowe.

“I think he lied to a grand jury and should be held accountable,” Ostrowe said Wednesday. “He spun the facts to get an indictment at any cost.”

In his December 2021 tort notice, Ostrowe’s attorney alleged that Helm told Ostrowe during the investigation that he was “sick of all the political bullshit.”

Drummond’s letter to Ostrowe questioned “the credibility of evidence presented to the grand jury” and said Hunter’s actions “compromised the integrity of the Office of Attorney General.”

“I recognize the hardship this has placed on you and your family. I sincerely apologize to you on behalf of the state of Oklahoma,” Drummond said. “Further, I have instructed my office to convert the dismissal of this matter into a dismissal with prejudice. This should be interpreted as my belief that you committed no wrongdoing and as such should not be subject to any further legal action pertaining to the charges.”

Asked about whether Ostrowe intended to continue his civil lawsuit against the state, Hunter and the three tax commissioners, Matt Felty, Ostrowe’s attorney, said conversations were ongoing.

“From the beginning, the case has been about exonerating David and exposing the injustice that he endured. This is a big step in that direction,” Felty said. “Right now, we are elated with General Drummond’s letter and decision to convert the decision to dismissal with prejudice. Further considerations will be made at a later date.”

Felty declined to say why Ostrowe’s lawsuit has not yet been served to the defendants. State law gives petitioners 180 days to serve a lawsuit. For Ostrowe’s case, that deadline would be at the end of February.

Ostrowe said “dropping the lawsuit was not a condition of the letter” but that he appreciated Drummond’s acknowledgment of what happened to him.

“The only quote I made on this thing on day one was, ‘Only in Oklahoma.’ I stand by my actions,” Ostrowe said. “We need to protect the people who want to protect the citizens, and General Drummond is doing that.”

Read Gentner Drummond’s letter to David Ostrowe

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