Keith Wilson Donated Widely to Other Candidates, Many of Whom Also Gave to Him

In recent weeks, trucking company owner Keith Wilson has emerged as a leading candidate for Portland mayor as voters search for an alternative to incumbent city commissioners.

For much of his run for mayor, Wilson has also built relationships with other candidates by giving small donations to their campaigns.

Wilson has given a donation to 49 other city office seekers, one per candidate, over the past seven months. Members of his family have also frequently contributed to other campaigns: His wife has donated 32 times, and his two college-aged children have donated 27 times and 25 times, respectively.

In 22 cases, all four members of Wilson’s family have donated to the same candidate. Another nine candidates received donations from Wilson and at least one other Wilson family member, most frequently Wilson’s wife, Katherine Wilson. Another several dozen candidates received donations from Keith Wilson only.

That appears to be the broadest use of campaign donations by any local candidate and their family. It raises questions about Wilson’s use of the city public campaign finance system.

Twelve city candidates are under investigation for agreeing in writing to reciprocal swaps of donations with other candidates in an effort to unlock matching taxpayer dollars. Such deals are likely a violation of state elections law, according to three elections lawyers.

Wilson is not under investigation and says he never agreed to reciprocal donations.

“I have not engaged in donation swaps with other candidates,” Wilson told WW in a statement. “I have always donated to candidates and causes I believe in and support, as has my family. In many cases, I let these candidates know that I supported them. In some cases, those candidates supported my campaign as well. I’ve made no promises, arrangements, or expectations of reciprocity between myself and other candidates.”

But 27 of the candidates who received donations from Wilson or one of his family members gave money to Wilson’s campaign. Only five of the candidates who received donations from at least two members of the Wilson family did not donate to Wilson’s campaign.

The generosity of Wilson’s children is also unusual.

Wilson’s daughter attends college in California, and his son attends college in Salt Lake City. In total, both of his children spent about $180 giving small contributions to candidates’ campaigns. Wilson’s daughter and son gave to nearly identical candidates, with the exception of two additional candidates that Wilson’s daughter contributed to.

All donations made by Wilson and his three immediate family members are listed as being made from the same home address in Northeast Portland.

An email obtained by WW shows that in July, Wilson emailed Jesse Cornett, who is running for City Council District 3, to say that Wilson and three family members had donated to Cornett’s campaign. Wilson then requested Cornett give to his campaign.

“Thank you also for the $20 to my campaign,” Wilson wrote. “Katherine [and his children] just donated $5 to your campaign. I am hopeful your family and friends would donate to my campaign as well.”

Cornett says he did not ask family and friends to donate to Wilson.

Timur Ender, a District 1 candidate, said that “Keith made an ask for me to donate to his campaign. I chose to donate because I’ve enjoyed getting to know him and his values throughout the course of his campaign.” Ender added that one of his campaign’s strategies was to “connect with previous Portland donors of our campaign and see if there were others in their family or network who could also donate. As part of that effort, I reached out to Keith to ask if there were others in his family who could also make a small contribution to our campaign.”

The candidates to whom Wilson’s family gave money span from progressive to moderate, across all four geographic voting districts, and from obscure to serious.

Wilson says that he and his family “discuss political candidates and causes as a family and often support them together. Given the open elections rules, we are far more impactful if we donate individually than as a single household.”

The two Wilson children in a statement said: “Portland is our hometown and the city we love. We often discuss politics as a family and talk about supporting various candidates. In this case, we both decided to make contributions totaling roughly $180 to help various candidates for office who we believe will do good things for Portland. Not all of those candidates received contributions from both of us and we were not reimbursed for the money we donated. We hope that our small efforts to help these candidates will ultimately make Portland a better place.”