Bend businessman Michael Sipe is the Republican nominee for House District 53.

No votes have been counted yet in the race for Central Oregon’s House District 53.

But Republican Michael Sipe is already winning the battle for campaign cash by a landslide over Democrat Emerson Levy. Sipe had received several hundred thousand dollars by early autumn, while Levy didn’t crack the $100,000 mark until two weeks prior to the Nov. 8 election day.

Campaign cash is especially important in a race for a newly redistricted seat without an incumbent on the ballot.

Rep. Jack Zika, R-Bend announced last year that he would not seek a third term in the newly redrawn House District 53.

Levy, a Bend attorney, lost to Zika in the 2020 – receiving just 42.8% of the vote. But that race used the old district lines, which stretched further south into rural areas of Deschutes County that have historically favored Republicans. The newly compacted district is more urban and Democratic-friendly. With Zika stepping down, businessman Michael Sipe stepped up to fight to keep the seat from turning red to blue.

Levy, a Bend attorney, is seeking to flip a longtime Republican-held seat. She attempted a run against Redmond Republican Jack Zika in the 2020 election, e. This election will be the first with newly drawn boundaries for District 53.

The new district encompasses northern Bend, southern Redmond and Sisters. With only a slight Democratic tilt, according to Dave’s Redistricting, a widely used website detailing demographics in new political districts for the 2022 election. According to its precinct-level breakdown, the area has voted slightly more often for Democrats than Republicans. The seat is seen as a toss-up.

Republicans are spending significant funds in an attempt to take Democratic districts in northwestern Oregon, the Willamette Valley around Salem, and in Ashland, a rare Democratic political outpost in the heavily Republican southwest.

While winning Democratic seats is the key to reducing Democratic majorities in the legislature, party leaders are also concerned about seats held by Republicans that after redistricting are less friendly to the GOP.

Sipe’s campaign has been flooded with contributions from Republican and business interests.

Sipe, a self-proclaimed “businessman, not a politician,” has received over $651,000 in total contributions through Oct. 27. He’s received $142,500  from the Bring Balance to Salem PAC,  according to the Oregon Secretary of State’s Office.

The Bring Balance to Salem PAC was created in November 2021 to boost Republican candidates for the legislature, as well as Republican Party political action committees. 

It’s earliest bankrollers were major timber, construction and business interests. Nike Founder Phil Knight is the largest contributor, giving a total of $2 million. Red Emmerson, the nation’s largest private landowner, has given $350,000 through his business, California-based Sierra Pacific Industries. 

The campaign consultant for Bring Balance to Salem PAC is former U.S. Rep. Greg Walden, R-Hood River, who served 20 years in Congress. As chair of the he National Republican Congressional Committee, Walden was the party’s lead fundraiser in Congress.

The Bring Balance to Salem PAC has raised just under $4.95 million in less than a year. It has given just under $534,000 to the Evergreen Oregon PAC, the campaign arm of House Republicans.

Evergreen Oregon PAC which has paid for social media advertising, surveys and polls for Sipe. The PAC is directed by Bryan Iverson, a Prineville-based political consultant who is also the husband of House Minority Leader Vikki Breese Iverson, R-Prineville.

Breese Iverson’s personal political action committee, Friends of Vikki, has pitched-in over $25,000 to buy for broadcast advertising for Sipe.

Initially, Sipe got his campaign up and running in January with a $50,000 loan from his own business, CrossPointe Capital, a mergers and acquisitions and business development firm for buyers, sellers and builders across the West Coast. Sipe is also chair of 10x Catalyst Groups, which is a Christian-focused networking group for CEOs and business owners. Previously, Sipe was the regional vice president of American Communications Network Inc., a multilevel marketing telecommunications company, which is the subject of a federal lawsuit alleging former President Donald Trump committed fraud. A 2009 video on Sipe’s YouTube channel shows his formal promotion to the position.

Fundraising complaint

Former District 53 candidate Eileen Kiely, who ran against Zika in 2018, filed a complaint against Sipe with the Secretary of State.

Kiely’s Sept. 30 complaint requested an investigation into an event hosted by Sipe’s campaign, the Central Oregon Business Forum. In the complaint, Kiely, a vice chair of the Deschutes County Democratic Party, alleged Sipe didn’t properly disclose campaign donations.

Sipe’s previous social media posts have also been the subject of online criticism, including COVID-19 misinformation and questioning the security of the 2020 presidential election, which has been proven to be legitimate.

“Regardless of who wins the presidential battle tomorrow, or if this battle continues on a while longer, we can’t forget that the battle is not the war, which will rage on no matter who becomes president,” Sipe wrote on Facebook the day before the Jan. 6 Capitol riots.

Sipe told The Bulletin after a Bend Chamber of Commerce debate in September that he accepts the results of the 2020 presidential election as legitimate.

“A lot of people should have voter remorse,” Sipe said, “but we know who the president is.”

Levy staying afloat

While Sipe has garnered significant financial support from statewide Republican committees, Levy has trailed behind with just over $118,000 in total contributions since she declared her bid in October 2021, which includes around $24,000 rolled over from her 2020 campaign. Like her previous run for the 53rd District seat, Levy has championed child care and clean energy as her priorities.

Levy has received only one large donation: $10,000 from the Local 48 Electricians PAC, which has poured hundreds of thousands of dollars into Tina Kotek’s gubernatorial campaign.

The Democrat has received $6,000 from Portland-based Women’s Investment Network PAC, which seeks to “support Democratic, pro-choice women candidates” for the Legislature. The PAC is directed by former Democratic state Sens. Jane Cease and Diane Rosenbaum.

The Future PAC, House Builders, the official campaign arm of Oregon House Democrats, contributed just over $3,500 Levy’s campaign. The PAC is run by Rep. Julie Fahey, D-Eugene, and Rep. Dan Rayfield, D-Corvallis, Speaker of the House.

Despite her lag in funding, Levy has earned incremental financial support from New York Times journalist and former gubernatorial candidate Nicholas Kristof, state Rep. Dacia Grayber, D-Tigard and the Kiely.

Ballots have been mailed voters. They must be returned by Nov. 8.

Oregon Capital Bureau Reporter Gary A. Warner contributed to this story.