(OKLAHOMA CITY, Okla.) — On Tuesday in Oklahoma, Republican Rep. Tom Cole, chair of the powerful House Appropriations Committee, will face one of his most significant and costly primary challenges since he went to Congress 22 years ago.

His leading opponent in the Republican contest for the 4th congressional district is deep-pocketed, out-of-state businessman Paul Bondar, who in March filed his bid to replace Cole the reliably red bastion.

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Bondar, a political newcomer who recently moved into Oklahoma from Texas, has spent millions of his own dollars to wage a lively race against a 10-term incumbent — investing more than $4.3 million in advertisements, the advertisement tracking firm AdImpact reported on June 11.

In the process, Bondar has made the unexpected Oklahoma contest the third-most expensive House primary of the year. Cole has spent over $3.1 million ahead of the race, according to Federal Elections Commissions filings, though he has significantly more money on hand than the largely self-funded Bondar.

Cole has “never had this much money against him,” said Fount Holland, a longtime Oklahoma Republican political consultant who worked for Cole more than a decade ago. Holland noted that the challenge was unusual, especially because of Cole’s deep relationships in the district.

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Former Republican Gov. Frank Keating, a fixture in Oklahoma politics going back two generations, said he was “puzzled” over Bondar’s run.

“There’s never been a bit of a suggestion that Tom Cole is not up to the job. Never been a bit of a suggestion that Tom Cole is not focused, hugely intelligent, hugely significant at what he does, and especially being chairman at the most powerful, certainly one of the two, perhaps or three, most powerful committees in the U.S. House,” Keating said in an interview with ABC News.

Cole served as Oklahoma’s Secretary of State under Keating and worked as the governor’s chief legislative strategist and liaison to the state’s congressional delegation.

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“There is no one more respected than Tom Cole. There really isn’t, and that’s why I was intrigued and puzzled by his opponent’s decision to run, not only in Oklahoma, but against a man like Tom Cole,” Keating added.

Bondar is challenging Cole from the far right, mounting a campaign focused on issues such as border security, energy independence and inflation, among other things. He has reserved his strongest criticism for Cole’s support of American foreign aid, especially money being sent to Ukraine as it battles Russia’s invasion from the east.

“For those of you who don’t know me, you soon will,” Bondar said during a speech at the right-wing Turning Point conference over the weekend in Detroit. “I am running for the United States Congress in congressional district four in Oklahoma, and you may ask me why. I am running to remove the global boot that silences the conservative voices across America and to bring back the voice of the conservative movement.”

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Former President Donald Trump has endorsed Cole. Bondar told ABC News over the weekend that the former president should “change his mind” and back him instead.

Cole has traded barbs with his opponent largely over questions surrounding Bondar’s residency. Bondar’s current address is in Texas, and he said he has leased a home in Oklahoma. His business he started — Bondar Insurance Groups — is based in Illinois with a location in South Florida.

Bondar has said he grew up in Wisconsin and spent much of his adult life in Illinois. He owned the Bondar Insurance Group in Oak Brook, Illinois, and moved to Texas in 2020, he told KFOR News in Oklahoma City.

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A report from The Oklahoman alleged that Bondar has tangential ties to a couple connected to Russian President Vladimir Putin. The report has led some party leaders in Washington to wonder whether Cole is being targeted because of his support for Ukraine.

Government records show that through business relationships in South Florida, Bondar’s wife may have a loose connection to a Russian pop star who has received awards from Putin — a tie that Bondar’s campaign rejects.

His wife Jennifer Bondar, as of 2023, is listed as the principal and manager of an LLC under a Florida address, according to the Florida Department of State Division of Corporations. The address, a condominium complex, is also where the Florida location of Bondar’s Insurance company is.

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Jennifer Bondar’s LLC is in a unit owned by a company called Muza Marin Inc, according to the Broward County Appraiser in Florida. Those records list the registered agent — or the person that is designated by an LLC to accept official documents on behalf of the small business — for Muza Marin, Inc. as Lioudmila Issakovitch.

Issakovitch is married to pop star Valery Leontiev, who has a well-established and public relationship with Putin. Leontiev is a recipient of a number of Russian awards from Putin, including the Order of Friendship in 2014 and the Order of the Fatherland in 2022, which he received just days before Russia invaded Ukraine. The performer also sang a duet with Putin at a 2006 conference with the leaders of other former Soviet Union republics.

Bondar and his campaign have rejected any connections between the candidate and the Russian couple, and have denied even knowing them. They say the only connection is that their business partner Maxim Mandric, who had lived in the unit associated with the LLC, had moved to another unit.

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“It’s important to note that the Bondars did not lease the unit and their business partner moved into another unit last year,” campaign spokeswoman Lisa Liebl told ABC News.

The candidate told ABC News in an interview on Saturday that his rise in popularity through the course of the race is “very similar to a Trump movement.” He also compared reports about his ties to Russians to the Trump-Russia investigation.

“That’s another reason why people think I’m President Trump — a fake, phony Russia-collusion story,” Bondar told ABC News.

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“Because of — I don’t even know, I had a 1099 worker who rented an apartment through a real estate company that was being sublet. And the singer … of that property sang [for] Putin’s party so they put on there: ‘Texan has ties to Russia.’ That’s very funny, because I’m actually have a little bit of Ukrainian in me, and it shows the desperation and it shows that we’re successful. It shows that our campaign is really a well-run campaign,” he added.

Bondar’s spokeswoman told ABC News the campaign is consulting with lawyers and considering legal action against The Oklahoman because of its report on claims of the possible Russian connection.

Thomas Graham, a distinguished fellow at the Council on Foreign Relations who was senior director for Russia on the National Security Council staff during the George W. Bush administration, noted that just because Leontiev has been seen publicly with Putin or has received awards from him, it doesn’t necessarily mean that the pop star and Putin are close.

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“He’s like any other politician. These people have all sorts of contacts with people, which doesn’t always indicate closeness,” Thomas said.

“The president of the U.S. hands out awards to people and may not have a personal relationship with them. Putin operates in the same way. He has a small circle of confidants and perhaps a broader circle of people he listens to when it comes to foreign policy … Then there’s a much broader group that he may sing duets with or give awards to.”

The possible connection, though, has raised eyebrows given the recent battles over continued funding for Ukraine’s war effort against Russia.

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Alexander Vindman, a retired National Security Council director of European Affairs, told ABC News that “whether or not Bondar knows it,” the Putin regime is capable of trying to leverage even loose connections to advance its own interests.

Vindman testified against then-President Trump when he was impeached in 2019 for abusing his power in connection with stalling a military aid package for Ukraine. Trump was acquitted by the U.S. Senate.

In addition to Bondar, Cole faces three other GOP primary challengers, Andrew Hayes, Nick Hankins and Rick Whitebear Harris. On Friday, in an unusual move, all three released a joint video announcing they would be backing Bondar over Cole, despite not having dropped out themselves.

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The combination of all four GOP challengers could lead to a runoff election if no one candidate wins 50% of the total vote. In that case, the top two vote getters would advance to a second round of balloting in August.

ABC News’ Hannah Demissie contributed to this report.

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