Is Oklahoma Pay-to-Play: Inside Oklahoma’s $200 Million Broadband Machine
How One Family Wrote the Checks, Landed the Appointments, and Collected the Grants
Statehouse Secrets is written by Jonathan Hewitt, an independent investigative journalist digging into money, power, and backroom deals at the Oklahoma Capitol.
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Part 1 of 2: Oklahoma’s Broadband Machine
If you want to understand how influence actually works in Oklahoma, you have to start with the people who have learned how to operate inside every part of the system at once.
This is not about one donation or one appointment. It is about a network that shows up in campaign finance, in state government, in regulatory boards, and in the flow of public money. At the center of that network is the Hilliary family.
Hilliary Communications is headquartered in Medicine Park, Oklahoma, but what exists today is far more than a local telephone company. The family controls a network of telecom entities, including Southwest Oklahoma Telephone Company, Oklahoma Western Telephone Company, Southern Plains Cable, Oklahoma Fiber Network, and additional operations in Texas and Iowa. Dustin Hilliary and Edward Hilliary Jr. serve as co-CEOs. Mike Hilliary operates as Chief Administrative Officer. Dino “Dean” Pennello serves as CFO.
Alongside that, the family controls Hilliary Media Group, which publishes The Southwest Ledger and The Chronicle and operates the Rural Oklahoma Network, including Radio Oklahoma Ag Network, Oklahoma Farm Report, Oklahoma Energy Today, and the Road to Rural Prosperity podcast. The same family receiving public broadband funding also owns a rural‑focused media network that syndicates content to more than 50 radio stations across Oklahoma.
That is the foundation.
The Money
The amount of public money flowing through Hilliary-controlled entities is not small and it is not speculative. It is documented.
Through USDA ReConnect grants, Hilliary entities have received tens of millions across multiple rounds. Oklahoma Western Telephone Company alone received $23.3 million in one round and nearly $25 million in another. Southern Plains Cable and Tatum Telephone Company received additional multi-million dollar awards.
At the state level, the numbers accelerate.
On December 17, 2024, Governor Kevin Stitt stood alongside the Oklahoma Broadband Office to announce a $43.2 million ARPA-funded broadband expansion project awarded to Hilliary Communications across 11 counties. That project included approximately $22.8 million in matching funds, bringing the total project to roughly $66 million.
In May 2025, the Oklahoma Broadband Office awarded an additional $40.9 million in middle-mile grants across multiple projects tied to Hilliary entities.
Pending BEAD awards add another estimated $60 million or more.
By Dustin Hilliary’s own biography on the State Regents website, the company had previously secured $110 million in federal broadband funding. That number is now outdated. When ARPA, middle-mile, and BEAD allocations are included, the total approaches $250 million.
A quarter of a billion dollars in public funding flowing through one family’s network of companies.
A link at the bottom of this article from the OBO website gives confirmation to the middle mile figures listed above.
The Donations
Now look at where their political money goes.
Since 2015, the Hilliary network has contributed more than $705,000 to political campaigns and PACs. Dustin Hilliary alone accounts for roughly $249,000 of that total.
To Governor Kevin Stitt, Hilliary Communications contributed $17,500 to his 2022 campaign and $5,400 in 2019. Edward Hilliary Jr. contributed $10,000 to Stitt’s leadership PAC, Big Ideas Create Excellence.
At the federal level, eight Hilliary executives contributed approximately $70,000 to Markwayne Mullin’s 2022 Senate campaign. Hilliary Communications added another $50,000 to Defend US PAC, a super PAC that spent more than $700,000 supporting Mullin.
Dustin Hilliary contributed to Donald Trump. The company contributed to the Republican National Committee. In the 2024 cycle alone, the network accounted for more than $400,000 in political contributions and $80,000 in federal lobbying expenditures.
Dustin Hilliary made the purpose of those contributions clear when he endorsed Mullin, stating that Mullin was the candidate most capable of bringing federal broadband funding back to Oklahoma.
That is not a vague statement. It is a direct link between political support and financial return.
The Appointments
The next step in the cycle is access.
Governor Stitt has appointed multiple Hilliary executives and family members to positions across Oklahoma government.
Dustin Hilliary was appointed to the Oklahoma State Regents for Higher Education in 2022 for a nine-year term. While writing this, Gov. Stitt announced another appointment for Dustin, this time to the University of Oklahoma Board of Regents.
In September 2025, he was elevated to Senior Advisor to the Governor, serving as a chief legislative negotiator while remaining co-CEO of Hilliary Communications.
Edward Hilliary Jr. was appointed to the OSBI Commission and also serves on the Oklahoma Workforce Commission.
Mike Hilliary was appointed to the Oklahoma Broadband Expansion Council, which acts in an advisory capacity to the Oklahoma Broadband Office; the agency responsible for awarding the grants flowing to Hilliary companies.
Dino Pennello, CFO of Hilliary Communications, was appointed to the Oklahoma Employment Security Commission, replacing Dustin Hilliary when he vacated that position.
These are not isolated appointments. They place the same network inside the structures that oversee workforce policy, economic development, and broadband funding.
The Halted Process
In 2023, Oklahoma’s broadband grant process was halted after the Attorney General’s office warned that the evaluation structure could create an unfair advantage for certain companies and could be subject to legal challenge.
The process was reset and reopened with assurances of transparency and fairness.
Despite that reset, Hilliary companies remained among the largest recipients of funding.
The question is not whether the process followed its rules on paper. The question is whether a process can function independently when the applicant’s network sits inside the governing board, inside the Governor’s office, and inside the political system funding it.
The same network appears at every stage, funding campaigns, shaping policy, and benefiting from the outcomes.
The Dark Money Layer
Everything so far is traceable. The filings exist. The appointments are public.
But there is another layer.
Prosperity Alliance, a 501(c)(4) nonprofit, reported over $11 million in revenue and is not required to disclose its donors. It contributed at least $1.25 million to Defend US PAC, the same PAC that received $50,000 from Hilliary Communications and supported Markwayne Mullin.
Governor Stitt’s own dark money structure, 46 Forward, was created in 2023. It operates as a nonprofit with no donor disclosure requirements. Its leadership includes Romney McGuire, Richard Tanenbaum, and Rudy Blanco, all tied to Stitt’s political network. Its PAC arm, 46 Action, has spent heavily in Oklahoma races, including supporting Stitt-backed candidates and attacking judicial opponents.
Donelle Harder, Stitt’s chief of staff and former campaign manager, served as treasurer for 46 Action and also donated to Kristen Thompson.
At the same time, the Dustin Hilliary is involved with multiple PACs. He is listed as the treasurer for the Working for Oklahoma’s Legislative Future PAC, and the Chairman of the Oklahomans for a Connected Future PAC.
Some of these PACs show little to no reporting activity.
That is the point.
Not all influence is meant to be visible.
How the System Works
Step back.
Hilliary companies receive public funding. That money supports business growth. The network contributes heavily to political campaigns and PACs. Those political relationships lead to appointments and access. Those appointments place the same network inside the structures that influence future funding decisions.
Donations flow in. Appointments follow. Grants flow out. And the cycle repeats.
No single step is illegal.
But the system, viewed as a whole, operates with a level of alignment that raises a fundamental question.
The Question
This is not about one grant or one appointment.
It is about whether a system can remain independent when the same network appears at every stage of the process.
In Part 2, we move from the system to a single case. One race. One senator. One household. And what it looks like when this same network shows up inside legislative power itself.
Link to OBO PowerPoint:
https://oklahoma.gov/content/dam/ok/en/broadband/documents/grant-programs/middle-mile/Middle-Mile-Awards.pdf