Anonymous Mailer Targets Chuck Gray Shortly After He Ok’s Other Mystery Mailers

A new anonymous mailer has surfaced targeting Wyoming Secretary of State Chuck Gray, accusing him of being a RINO and abandoning Republican values. The mailer comes shortly after he determined a pair of unrelated anonymous political mailers were legal.

Leo Wolfson

February 07, 20246 min read

Chuck gray mailer 2 7 24
(Cowboy State Daily Staff)

Anonymous political mailers appear to be all the rage these days in Wyoming. A new mailer has surfaced targeting Secretary of State Chuck Gray.

The timing of the mailer is notable as Gray recently determined two anonymous mailers targeting state Reps. Steve Harshman, R-Casper, and Barry Crago, R-Buffalo, last fall were legal.

Those mailers were not labeled as paid for by any group, which is required for any campaign literature under Wyoming law.

 After complaints were filed on the mailers with his office, Gray determined that the mailers were legal, finding they do not advocate voting for or against a specific candidate, and were sent outside of the 30-day time period before primary elections when electioneering communications are restricted in Wyoming.

A complaint on the Crago mailer was filed by Johnson County Attorney Tucker Ruby, while a complaint on the Harshman mailer was filed by Casper resident Joann True. 

Gray determined both complaints did not have merit.

If Gray had determined the mailer complaints had merit, they would have been handed off to the Wyoming Attorney General’s Office to investigate the matter.  

A different, semi-anonymous mailer was put out in Sheridan County in 2022 that targeted four people there. None of the four were running for public political office, but one was a current office holder and all were politically active to some degree. 

This mailer differed from the Crago and Harshman mailers in that there was a group listed as connected to it, even though it wasn’t registered to the state. It also was sent out during the 30-day primary season window. 

A Sheridan County Sheriff’s office investigation determined who it believed was behind the mailer, but the local county attorney’s office determined that since none of the targets were running for public office, elections-related laws did not apply to the political mailer.  

A complaint was then filed with the Wyoming Secretary of State’s office about this mailer and Gray found merit to the complaint, forwarding the case to the Attorney General’s office. 

  • Chuck gray mailer 2 2 7 24
    (Cowboy State Daily Staff)
  • Chuck gray mailer 2 7 24
    (Cowboy State Daily Staff)

Tables Turned

The new mailer against Gray accuses him of being a “RINO,” a popular moniker for “Republican In Name Only,” and abandoning Republican values. 

It also criticizes him for a recent request he made before the Joint Appropriations Committee to increase his individual department’s budget by more than 30%. The mailer said he wanted to increase the state’s budget by 30%, but Gray’s request was limited to his individual department.

This request was made to facilitate the purchase of a new online computer filing system for his department. 

“We’ve been duped by RINO Chuck Gray,” the mailer reads.

 It also mentions how his father, Jan Charles Gray, donated the vast majority of funds to Gray’s 2022 secretary of state campaign, a sum of $500,000. The mailer claims this donation equated to an act of buying the election.

The anonymous mailer was sent from an address connected to a UPS store in Fargo, North Dakota. 

What Gray Says

Gray told Cowboy State Daily the mailer contains “a bunch of lies” concocted by donors affiliated with Hillary Clinton and George Soros.

“The insiders and their friends in the media can’t win on the facts so they just make it all up, recycling their lying tactics,” he said.

In the waning days of the 2022 secretary of state campaign, a Federal Election Commission complaint was filed on Gray by former Wyoming Secretary of State Max Maxfield. Gray was eventually cleared on the complaint last spring.  

“Just like when they put forward the false, leaked Maxfield complaint two weeks before the 2022 primary, the insiders planted the false story with the media and then followed it up a few days later with a cheaply made mailing full of lies,” Gray said.

The Request

Gray made his $3.1 million budget increase proposal to the Appropriations Committee last December to pay for a new enterprise system that would allow his department to handle an increase in business without adding employees.

The Secretary of State’s office has experienced an increase in business filings over the last few years, which resulted in a corresponding $8.5 million increase in revenue in 2023 and more than $60 million in revenue over the last biennium.  

“The inability of the Clinton/Soros donors funding this mailer to understand how our agency is one of the few in government that actually brings in money, and that has grown 300% in volume in six years, shows just how much they do not understand how to run a business,” Gray said.

Gray said the new system would actually save the state money in the long run by preventing staff increases.

The Appropriations Committee rejected the request, expressing concerns that Gray hadn’t publicly bid out the project, and some expressed criticism that Gray would never have accepted a proposal like this when he was in the Legislature.

“The claim by insiders, Cowboy Stater Daily, and now the insider donors funding this mailer equating a one-time expenditure to upgrade our business filing system to respond to our state’s exponential growth in filings and claiming that is a recurring increase in our budget is misleading and absurd,” Gray said. 

Gray also believes the mailer was made in an effort to “intimidate” him for his ruling on the Harshman/Crago complaint, and his efforts to prevent former President Donald Trump’s name from being removed from Wyoming’s election ballots this fall.

“The Clinton/Soros donors funding this are clearly upset about my work to make sure Trump will be on the ballot,” he said.

In a January meeting, the appropriations committee also rejected a request from Gray’s office to add $75,000 to its budget for various fraud protection and investor education efforts.

At that meeting, Rep. Tom Walters, R-Casper, mentioned how the Secretary of State’s office already spends around $750,000 on a securities fund.  

Gray said this fund solely supports auditor salaries and cannot be used for creating verbiage about alerting investors about fraud risks, an effort that had been previously supported by a federal grant.

Leo Wolfson can be reached at

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Leo Wolfson

Politics and Government Reporter