Oklahoma’s Crony Class: How Connected Families and Dark Money Have Captured State Government
How the Hilliary Family, Chuck Hall, and Governor Stitt Turned Taxpayer-Funded Broadband Programs into a Closed System of Political Favoritism
By Marven Goodman
Investigative Article
July 22, 2026 — Oklahoma was once known for a healthy skepticism of big government. Today, that spirit has been replaced by a comfortable arrangement between politicians, well-connected families, and taxpayer-funded programs. What we are witnessing is not limited government, it is government being used as a tool for insiders to enrich themselves while ordinary Oklahomans foot the bill.
At the center of this growing problem sit two powerful families and the politicians who enable them: the Hilliary family of southwest Oklahoma and the Hall brothers of Perry. Their story, along with the active participation of Governor Kevin Stitt, reveals a system where political connections, dark money, and government grants have become deeply intertwined, including a troubling overlap between the Hilliary Communications empire, the Oklahoma Broadband Office, and the newly created Invest in Oklahoma Board.
The Hilliary Family’s Government-Assisted Empire
Hilliary Communications, run by brothers Dustin and Edward Hilliary, has aggressively expanded in recent years. In 2025, the company acquired TDS Telecom’s Oklahoma operations, adding nearly 35,000 new customer locations. They have also moved into mainstream media, purchasing the Lawton Constitution newspaper and acquiring radio stations.
While they grow through acquisitions, Hilliary Communications has simultaneously become one of the largest recipients of government broadband funding in the state. The company and its affiliates have received more than $110 million in federal and state broadband grants and loans. This includes a $65.9 million project launched in late 2024 with $43.2 million in federal ARPA funds approved by the Oklahoma Broadband Governing Board.
These are not small, targeted projects. They represent a direct transfer of taxpayer resources to a single family-owned company. At the same time, Hilliary executives have been active political donors to Governor Stitt’s campaigns and have benefited from multiple appointments by Governor Stitt, including Dustin Hilliary’s placement on the OU Board of Regents and the Oklahoma State Regents for Higher Education.
Here is how that went down . . . In 2022, Oklahoma Governor Kevin Stitt appointed Dustin J. Hilliary of Lawton to the Oklahoma State Regents for Higher Education for a nine-year term ending in May 2031.
As co-CEO of the family-owned Hilliary Communications, a telecommunications company, Hilliary was selected by Stitt to serve on the constitutional board that coordinates Oklahoma’s public higher education system. That appointment received significant public attention because Hilliary does not hold a college degree. He later resigned from the State Regents in 2026 after Stitt appointed him to the University of Oklahoma Board of Regents, still with no college degree.
A Costly Choice: Fiber Over Competition
If the Oklahoma Broadband Office were genuinely interested in delivering affordable, high-speed internet to rural Oklahomans as quickly and cheaply as possible, it would have taken a very different approach. Instead of pouring tens of millions of taxpayer dollars into expensive fiber optic buildouts that primarily benefit companies like Hilliary Communications, our State Legislature could have opened the process to true competitive bidding and at least considered satellite technology.
Starlink, for example, currently offers rural residents reliable broadband for roughly $55 per month with no massive taxpayer-funded infrastructure required. Yet the state has largely chosen to subsidize the construction of very costly fiber networks across difficult rural terrain, networks that take years to build and cost far more per household than satellite alternatives. This approach has funneled enormous sums to politically connected providers while delivering more expensive solutions for the very rural communities the Oklahoma Broadband Office program claims to serve.
By favoring large fiber grants over market-driven solutions like satellite internet, the Oklahoma Broadband Office has effectively picked winners, and Hilliary Communications has been one of the biggest. This is not efficient governance. It is government choosing the most expensive path to enrich their well-connected players under the banner of “rural economic development.”
A Troubling Overlap
Hilliary, Broadband Grants, and the Invest in Oklahoma Board
There appears to be a clear connection between the Hilliary Communications empire, the Oklahoma Broadband Office, and the Invest in Oklahoma Board.
Hilliary has been one of the biggest winners in the state’s broadband grant programs, receiving tens of millions of dollars in taxpayer-backed funding. At the same time, the Legislature created the Invest in Oklahoma Board, a new body designed to direct state pension and trust money into Oklahoma-based investments. Senator Chuck Hall co-sponsored the legislation that established this board. Shortly afterward, his brother, Zack Hall, was appointed to that board by the Senate President Pro Tempore.
While there is no public proof of direct coordination, the pattern is difficult to ignore: a company that has received massive government broadband grants now operates in an environment where a new investment board, created with help from the powerful Senate Appropriations Chairman, has placed a member of a politically connected family in a position to influence how state-related capital is deployed. This overlap between broadband funding and the new Invest in Oklahoma program creates a closed loop in which politically connected players can benefit from multiple streams of government financial support.
But Wait, There’s More
Dark Money and the Oklahoma Conservative Coalition
The Hilliary family’s political activity extends beyond standard campaign contributions. Hilliary Communications donated $50,000 to the Defend US PAC in 2022. More significantly, there is a direct operational link between the company and the Oklahoma Conservative Coalition, a Super PAC that has spent heavily in recent elections.
The Coalition has used Hilliary Communications’ headquarters address in Medicine Park for its bulk mail permit. A person connected to Hilliary has been tied to the group’s mailings. This same group sent dark money-style mailers supporting Sen. Chuck Hall during his 2026 primary and has spent millions attacking other Oklahoma Republican candidates, candidates they can’t control.
In one reported instance, the Oklahoma Conservative Coalition received $2.3 million from out-of-state dark money organizations. This creates a troubling pipeline: a company receiving tens of millions in government broadband grants connected to a dark money operation that supports politicians positioned to protect those very funding streams, including those who helped create new investment vehicles like the Invest in Oklahoma Board.
Chuck Hall and the Family Appointment Game
Senator Chuck Hall of Perry serves as Chairman of the Senate Appropriations and Budget Committee, one of the most powerful positions in state government. His brother, Zack Hall, was appointed in January 2026 to the newly created Invest in Oklahoma Board.
Chuck Hall co-sponsored the legislation that created this board. The board was designed to direct state pension and trust money into Oklahoma-based investments. Zack Hall, who works at the family bank as CEO/President where Chuck serves as Chairman of the board, was then handed a seat on it.
This is not subtle failure of government, not at all. A sitting senator helps create a new investment vehicle, and his brother is promptly appointed to help oversee it. Chuck Hall’s position as Appropriations Chairman gives him enormous influence over state spending decisions that can directly or indirectly benefit companies receiving government support. The appointment of his brother only deepens the appearance of a closed system designed to benefit politically connected insiders, especially when that same family network has already benefited substantially from broadband grants administered through the Oklahoma Broadband Office.
Governor Stitt’s Role in this Corrupt System
Governor Kevin Stitt has played a central role in enabling this environment. His administration has overseen the distribution of massive federal broadband funds through the Oklahoma Broadband Office and Governing Board. At the same time, Stitt has appointed Dustin Hilliary to multiple high-profile positions and has generally shown little interest in reining in the growth of government programs that create opportunities for political favoritism.
Rather than using his office to shrink the size and scope of government and reduce opportunities for cronyism, Stitt has presided over an expansion of state involvement in broadband, economic development, and investment programs. These programs, sold as economic development, have instead become vehicles for well-connected interests to access taxpayer resources and political protection, including through the new Invest in Oklahoma Board.
A Pattern of Insider Governance
What we are seeing in Oklahoma is not isolated. It is a “feature” of big Government:
* Companies receive large government grants while their executives and associated groups engage in dark money political activity.
* Legislators create new boards and programs, then see family members appointed to them.
* Powerful committee chairmen maintain influence over the very funding streams that benefit politically connected businesses.
* Dark money groups operate with addresses and personnel tied to major grant recipients.
* New investment vehicles like the Invest in Oklahoma Board emerge alongside existing grant programs, creating multiple avenues for connected players to benefit.
This is not limited government. This is government that has grown large enough and complex enough to be captured by those with the best political connections. Every new program, every new grant, and every new board creates another opportunity for insiders to benefit while the public pays the cost and receives little in return.
The Real Solution
Oklahomans who believe in limited government, lower taxes, and reduced regulatory control should recognize how the current system works against those principles. Expanding government programs, whether in broadband, economic development, investment, or fractional reserve banking, does not shrink the state. It creates new centers of power that inevitably attract political influence and favoritism.
The proper response is not to create more programs or more oversight boards. The proper response is to reduce the size and scope of government so there are fewer opportunities for connected families and dark money operations to game the system. My friends and associates call this “Starving The Beast”. When government has less money to hand out and fewer favors to grant, the incentive for this kind of insider behavior shrinks dramatically.
Until that happens, expect more of the same: well-connected companies like Hilliary Communications receiving taxpayer-funded grants, dark money groups protecting their interests, and family members of powerful legislators landing appointments to the very boards that help direct state resources, including the new Invest in Oklahoma Board.
This is not how limited government is supposed to work. It is how government grows like a cancer, pretending to serve the public.
In Closing
What we are seeing in Oklahoma this is not an isolated scandal but a clear and recurring pattern of crony capitalism. The Hilliary family has built a growing communications and media empire by receiving over $110 million in taxpayer-backed broadband grants, all while maintaining operational ties to dark money groups like the Oklahoma Conservative Coalition. At the same time, Senator Chuck Hall, who chairs the powerful Senate Appropriations and Budget Committee, helped create the Invest in Oklahoma Board, to see his brother appointed to it shortly afterward. Governor Kevin Stitt has enabled this system through appointments and by presiding over the expansion of government programs that create new opportunities for political favoritism.
This arrangement represents the opposite of limited government. Instead of reducing the size and scope of the state, Oklahoma has created new boards, grant programs, and investment vehicles that inevitably attract insiders. When government controls large sums of money and picks winners through broadband grants, investment boards, and regulatory favoritism, those with the best political connections will always find a way to benefit. The result is higher costs for taxpayers, more expensive and slower solutions for rural Oklahomans, and the steady erosion of public trust.
Until Oklahomans demand a genuine reduction in the size and power of state government, this cycle will continue.
More programs will be created, more grants will be awarded to connected interests, and more family members of influential politicians will find themselves on newly formed boards. Real reform will not come from adding more oversight or creating additional layers of government. It will only come when we shrink the state’s role in the economy and stop giving politicians and their allies so many tools to reward themselves and their allies at the public’s expense. In order to do that, we must continue to elect members to the Oklahoma House of Representatives that support “Starving The Beast”, eliminating waste, fraud, and the abuses outlined above associated with large state government.
Please feel free to read our earlier articles on this topic:
Dark Money Mailers Swamp Rural District 38
Dark Money Mailer Boosting Curtis Erwin Targets Principled Conservative Dusty Deevers
Dark Money Mailers Hit Rural Oklahoma: Madison Bolay’s “Independent” Boost from Virginia Nonprofits Raises Big Questions for Limited-Government Conservatives
Brothers on the Bridge: How Oklahoma’s Powerful Senate Appropriations Chairman Helped Steer His Sibling onto the Board Overseeing Billions in Taxpayer Investments