In Wyoming elections, Trump giveth and Trump taketh away.
He’ll endorse some candidates on Election Day and others more than a year before they can even file to run.
A three-time general-election favorite of the reddest state in the nation himself, Trump’s picks almost always win the state’s Republican primary elections.
The president has not endorsed anyone in Wyoming’s most bitter struggle for statewide office, the nine-candidate field of Republicans vying for U.S. House.
It’s unclear if he will. The election is Aug. 18.
One of the nine GOP candidates, conservative activist Steve Friess told Cowboy State Daily in a Friday interview that he’s heard he’s under consideration for an endorsement.
The White House did not respond to a request for confirmation by publication.
Certified public accountant and political analyst Bill Cubin — son of former U.S. Rep. Barbara Cubin — said in his own Friday interview that it wouldn’t surprise him if Friess has been getting “positive comments” from the Trump inner circle.
“I’ll bet you privately, Chuck Gray is too,” added Cubin.
‘Trump World'
Secretary of State Gray, Friess, and seven other Republicans are running for the GOP nomination to the seat after U.S. Rep. Harriet Hageman announced she’s leaving it to run for Senate.
The other candidates are: state Senate President Bo Biteman, former Superintendent of Public Instruction Jillian Balow, military veterans Kevin Christensen and David Giralt, former legislator Keith Goodenough, actor/singer Richard Dodson and Casper businessman Reid Rasner.
“It’ll be interesting to see what they do,” said Cubin of Trump’s top staffers, whom he calls “Trump world.”
“My personal opinion — if, you know, I’m connected to Trump world — my message to the president would be, there’s no reason to endorse anybody,” said Cubin. “Because whoever you get is going be your ally in the House.”
Wyoming hasn’t elected a Democrat to its lone U.S. House seat in 50 years.
The first criterion in winning a Trump endorsement is past support for Trump, said Cubin.
Plus, he said, the president likes to win.
“They’re going to pick someone that they think has a good chance of winning,” said Cubin. “Or they’ll pick an opponent of someone they hate.”
Projecting electoral victory also sends the message, “We run the Republican Party,” he added.
On Election Day
President Donald Trump endorsed Steve Friess’s late father, Foster Friess, for his gubernatorial run on primary election day in 2018.
The last-minute move wasn’t enough to get the Republican over the finish line, and he finished second place with about 26% of the vote after now-Gov. Mark Gordon, who won 33.4% and went on to win the general election.
Now-U.S. Rep. Hageman finished third in that race with about 21% of the vote, and three more Republicans trailed.
Trump later told the Daily Caller that he’d come to realize that by the time he endorsed Foster Friess, “almost 70% of the vote was already cast."
Foster Friess had shown a newsworthy support of Trump, opting to give the presidential hopeful financial backing in 2016 — a move USA Today called “a sign that more of the party’s moneyed elite are rallying behind Trump’s unconventional White House campaign.”
On the other end of the timing spectrum, Trump endorsed U.S. Sen. Cynthia Lummis for reelection 14 months before she could legally file to run again.
And Lummis later chose not to run again.
Wyoming’s primary election, which tends to be more decisive than its general election, falls around the third week in August.
More timely were Trump’s past endorsements of U.S. Sen. John Barrasso (July 31, 2018), Hageman for Senate (Dec. 23, 2025), and state Senate candidate (now-U.S. Attorney for Wyoming) Darin Smith (July 27, 2024).
The Switcharoo
Trump endorsed Brian Schroeder in the 2022 race for Superintendent of Public Instruction, but Megan Degenfelder won.
It was the president’s second high-profile endorsee loss in a Wyoming race.
This cycle, Trump endorsed Degenfelder in her bid for governor on Jan. 9 — seven months before the election and three days before she publicly declared the run.
Cubin noted that Hageman, a Trump ally, has also endorsed Degenfelder.
That may be the right race for calling out preferences, said Cubin.
“Because there are only 50 governors in the country, you know,” he said.
Conversely, the House and Senate are more crowded arenas, with 437 representatives and 100 senators respectively.
Also in 2022, Trump endorsed Gray for secretary of state, and state Treasurer Curt Meier for reelection.
Both won.
Trump pointed favor toward Gray again in 2023, by linking to a Washington Examiner story that covered in part a Laramie attorney’s challenge against Gray’s office, against Trump’s eligibility to appear on the Wyoming ballot.
Trump also gave Biteman an attaboy in 2025 for the Senate president’s efforts in passing school-choice legislation.
Oh, Cheney
No Wyomingite is referenced more on Trump’s TruthSocial page than former U.S. Rep. Liz Cheney, his sworn enemy.
The Republican delegate helped to investigate Trump as part of the U.S. House Select Committee to Investigate the Jan. 6, 2021, attack on the United States Capitol.
It’s often called the J6 Committee.
Trump speculated in May 2022 about Cheney dropping out of the race rather than filing for reelection. He held a massive rally in Casper that month to raise money for Hageman’s challenge against Cheney.
Trump called Cheney a “sanctimonious loser” one month before her 2022 primary election.
He exulted for months after Hageman beat Cheney overwhelmingly. He derided Cheney again on Jan. 3, 2025, calling her a “Warmonger of low intelligence.”
Clair McFarland can be reached at clair@cowboystatedaily.com.
