The Oregon GOP’s New Chairman Brings Some Baggage to His Role

November’s election told the Oregon Republican Party it needed a fresh start. While voters nationally returned President Donald Trump to the White House, it was a different story in Oregon, where Republicans lost the 5th Congressional District seat; lost all statewide contests; and lost a seat in each legislative chamber, returning the Democrats to supermajorities in both.

With that difficult outcome in mind, five Republicans competed in February to become the next chairman of the Oregon GOP. It’s a position with significant sway over the party apparatus. The chair hires and fires party staff, appoints committee members, and directs fundraising and efforts to mobilize the grassroots.

In a Feb. 16 YouTube interview with a GOP political consultant, the eventual winner, Gerald “Jerry” Cummings, 51, a pastor and insurance agent from Columbia County, sketched out a path to success for his party in Oregon, saying Republicans should spend less time “tangled up in social issues” and focus on building the party rather than on angry rhetoric and internecine warfare.

“We need to reach beyond the Republican base,” Cummings said, “and do a better job of presenting a message that makes us contenders around the state.”

GOP delegates responded, electing him as their new chair Feb. 22.

“Jerry Cummings brings to the new role decades of leadership experience in politics, business, and community service,” the party said in a statement. “His background as a Baptist minister, small business owner, and media professional equips him with the necessary skills to unite and energize the party.”

But the Oregon Journalism Project has learned that along with those assets, Cummings brings to his new position some baggage.

Court records provide details from a long-running divorce and custody case, which stretched across three counties and lasted nearly a decade, that raise questions about Cummings’ ability to set the tone his party desires. More recently, lawsuits filed by Cummings’ creditors undercut his suitability for a role that requires managerial acumen and financial skills.

Bob Tiernan, a former lawmaker, GOP party chair and the runner-up in the 2022 GOP gubernatorial primary, says he’s disappointed that Cummings is leading the party. “We need the strongest possible people there,” Tiernan says. “We need somebody that doesn’t have damaging accusations against them—whether they are true or not.”

In 2009, Cummings’ then-wife filed for divorce in Coos County.

In court records, which have never been previously reported, Cummings’ ex-wife, a pastor’s daughter, said the couple met in the Portland area when she was 16 and he was 26 and an associate pastor. “On occasion, he would visit [her] when her parents were out of town and take her to hotels,” a trial memo filed by her attorney says. “He persuaded her that her parents did not truly love her as only he did, and that having sex with him at such a young age was appropriate.”

The couple married in 2003, when she was 19. “From the beginning of and throughout their marriage, [Cummings] would tell [his then-wife] about his sexual fantasies with young girls while they were having sexual intercourse,” the trial memo says. “He promised not to act on those fantasies so long as [his then-wife] allowed him to do whatever he wanted in their sexual relationship.”

But in a handwritten application for a restraining order coinciding with the divorce filing, the woman said her husband’s behavior spun out of control.

“I was handcuffed and hit with hangers,” she wrote. “Early in the marriage, he had a whip he hit me with.”

She added other allegations, including spousal rape. “He forced me to have sex with him and caused injury,” Cummings’ ex-wife wrote. “He has threatened if I don’t perform sexual activities, he will perform sexual activities on minors and he mentions them by name.” (OJP is not naming Cummings’ ex-wife because of her allegations of sexual violence.)

A judge in Douglas County granted the restraining order and would later renew it. Cummings was never arrested or charged for any of the allegations in the restraining order.

The court granted Cummings’ ex-wife custody of their children. When he later sought to change the terms of a parenting plan, the court required both parents to undergo psychosexual evaluations. Records show his ex-wife completed her evaluation but Cummings never came up with the payment for his.

In response to written questions from OJP, Cummings denied his ex-wife’s account of their relationship. He notes that although a judge twice granted a restraining order against him, a second judge later in the process rejected her application to continue the order.

“I never assaulted my wife or threatened her or anyone else, and we never had any sexual activity that was nonconsensual,” Cummings says. “I never touched another person in a sexual or romantic way during our marriage.”

He adds that much of what appears in the court record is untrue. “I have maintained for almost 16 years that my former spouse committed multiple acts of perjury, and she has stuck by her story,” he says. “What is true is that I was a terrible husband, and [she] and I, both victims of early sexual assault, had a very unhealthy marriage.”

Around 2010, Cummings moved to Washington, where he’d grown up before earning four degrees from the School of Biblical & Theological Studies in Lake Charles, La. In Washington, he won a school board seat and established a media company. He moved back to Oregon around 2018 and, according to his LinkedIn page, later opened an insurance agency in Beaverton and served as a pastor in St. Helens. From his home in Columbia County, he got involved in GOP politics, but records show his businesses struggled.

In June 2024, a collection agency sued him in Washington County Circuit Court on behalf of OnPoint Credit Union, alleging he’d deposited about $17,000 in bad checks and then withdrawn cash against them. Cummings did not respond to the lawsuit. Then, in December 2024, Washington Trust Bank sued Cummings in Multnomah County Circuit Court, alleging he’d borrowed $93,000 and failed to pay any of it back. Cummings hasn’t yet responded to that lawsuit.

He acknowledges financial struggles.

“The insurance industry has been very difficult these past two to three years, and the state of the economy has not helped,” Cummings says. “My wife and I have chosen not to take the road of putting our LLC businesses into bankruptcy. It is my hope that we can work out a settlement with payment terms we can make as we rebuild our businesses.”

Cummings says the difficulties he’s faced do not disqualify him for party leadership but rather make him relatable to those he helps to guide and lead.

“There will be some who can relate to a small-business couple in Oregon having their business in trouble right now,” Cummings says. “Many families can relate to messy divorces.”

He says he’s been open with others, including the churches he’s served, about his past: “Oregon Republicans have chosen to trust me based upon my record in Oregon as a party leader.”

One of the candidates Cummings defeated for the chairmanship, Ben Edtl, says the state deserves better: “Oregon needs a strong Republican Party so we can get some balance around here. For the betterment of the party and for Oregonians across the state, I think Cummings should step down.”

Correction: This story originally included an incorrect name for the School of Biblical & Theological Studies, where Cummings received his degrees. OJP regrets the error.

This story was produced by the Oregon Journalism Project, a nonprofit newsroom covering Oregon.