Secretary of state's deputy rose despite past IT debacle
This article has been updated with the news that Secretary of State Dennis Richardson won't be attending the Oct. 16 meeting of the State Land Board, contrary to an earlier statement.
A little over five years ago, Leslie Cummings was in danger of being fired or demoted by the state of Oregon.
Today, she's overseeing state elections during one of the most closely watched gubernatorial races in recent memory.
She is the second-in-command to one of the top statewide elected officials, Secretary of State Dennis Richardson — legally possessing all his authority, running the office's day-to-day operations, including overseeing audits as well as elections.
Richardson is now battling brain cancer, which was diagnosed earlier this year. And while his office has maintained he is doing well, on Monday he told other state officials he is unable to attend meetings of the State Land Board on which he sits, according to a Willamette Week article Tuesday. His perfomance at the previous meeting in August by phone had raised questions. On the afternoon of Oct. 12 his spokeswoman told the Tribune he would in fact be at the Oct. 16 meeting ,and his "treatment is going great."
Regardless, Cummings said the state is ready for the vote. She said the state is "working hand in hand" with county election officials. As far as hacking, she said, "I'm very confident that we won't have any security issues this election ... The people of Oregon can be very proud" of the state's readiness.
That Cummings is in a high-ranking position over the state's imminent election underlines her ascent in state government.
It also illustrates that she is poised to take over that office should the unexpected happen, such as a turn for the worse by Richardson.
Richardson recently conceded he doesn't come into the office as much due to the treatment he is undergoing. But says he doesn't intend to resign — and on Friday even indicated to the Tribune that he hopes to run for reelection.
"I will not be stepping down, and I hope to work with Leslie for the next six years," he said in an email response relayed through his chief of staff, Debra Royal.
With Richardson less present in Salem, however, Cummings' position has taken on more importance. The tight race between Gov. Kate Brown and challenger Rep. Knute Buehler puts a spotlight on the state elections office that Cummings oversees.
Not only that, but should Buehler win and Richardson's condition worsen, Cummings' chances of someday being named secretary of state would improve substantially.
That's because when a secretary of state steps down, it's up to the governor to appoint the interim replacement, much as Brown did when she left that position to become governor in 2015.
Compared to Brown, Buehler would be more likely to defer to his fellow Republicans' wishes on selecting an interim replacement, such as if Richardson recommends Cummings.
Interims can last a long time. Brown's choice to replace her in March 2015, Jeanne Atkins, served as secretary of state until January 2017, when Richardson took over. Atkins, now head of the Democratic Party of Oregon, said she doesn't know that Cummings would necessarily be appointed or run for office if Richardson steps down. But she added the deputy secretary's position "is very important" and Cummings could have a leg up. As deputy, she "would have had experience with all of the aspects of the office," Atkins said.
As for Cummings, when asked repeatedly if she would seek to succeed Richardson, including by running in an election, she did not rule it out. "I haven't even thought about that. I work every single day. These are not short days ... Dennis continues to be heavily involved. I speak with him almost every single day ... If things change we'll worry about it when it changes; for right now, there's no need to worry."
So who is this influential person?
The hiring of Cummings by Richardson shortly after taking office shed light on a backchannel and alliance that Richardson had as a Central Point lawmaker with her husband, Bob Cummings, an IT oversight analyst for the Legislative Fiscal Office.
In late 2012, Leslie Cummings was an IT manager at the Oregon Employment Department, when the security project she oversaw had repeated problems and cost overruns and was dubbed "fatally flawed" by a consultant. It was shelved by management at OED.
It was her husband's job to oversee such projects and advise lawmakers, and documents obtained by reporters Molly Young and Rich Read of The Oregonian in 2013 showed he praised his wife's project to her superiors and promised "minimal overreaction" by lawmakers if it failed, leading to an ethics complaint.
The complaint to the Oregon Government Ethics Commission filed by employment department finance manager George Ostertag alleged that Cummings' husband "inappropriately" used his position to get an IT oversight hearing that had been planned by Richardson canceled. It would have focused on Cummings' wife's project, which was very late and very over budget, "with no end in sight," Ostertag complained.
The complaint also claimed that Cummings was in danger of being fired, and Cummings' husband used his relationship with the top IT manager for the Oregon Health Authority and the Department of Human Services to get Cummings a job there instead — even as her husband was overseeing those agencies' work on Cover Oregon, the $300-million project that was soon to become the next big IT debacle.
Though the complaint was rejected by the ethics commission, Ostertag told the Portland Tribune he was concerned by Cummings' management style, especially since her project — the security log-on to the department website, essentially — was deemed unworkable for outside businesses to use.
"She was more than given an opportunity to make that thing work," Ostertag said. "To the bitter end I don't think she ever acknowledged it was not going to work."
Ostertag told the Tribune that Cummings and other employees that OED management filed complaints that he said were misleading and inaccurate. He said they were reacting to management pressure to fix problems and do their jobs.
Cummings, for her part, says the audits were wrong. She and about 20 other "whistleblowers" shared information regarding "bad management" at OED, and she sought other employment when she faced retaliation. The top managers at OED were ousted, though one secured a large settlement.
Richardson, others praise
Earlier this year, Richardson told the Tribune he "did deep research on what had taken place" before hiring Cummings, and that past news coverage was wrong.
"She was being set up to take a fall ... She is so qualified. I don't know anybody who is more qualified for this job than her."
He said he was warned against hiring Cummings as well as another former official, Steve Trout — who'd been let go by then-Secretary of State Kate Brown — due to the perception it raised.
"I was told you can't hire these people because it will look bad. And I said I'm willing to take the heat because I want the right people," Richardson said.
Cummings referred the Tribune to a friend of Cummings who worked with her at OED, Tracy Martineau. Martineau said she had no first-hand knowledge of the IT problems there, having left in 2010. But she praised Cummings as a very organized and principled manager.
Roland Rivera, a longtime IT manager who works under Cummings, praised her as "one of the best bosses I've had in my entire working career," saying, "She will allow you to do your job without micromanaging."
Cummings was born in California and moved to Oregon when she was 5, living on a farm outside of Eugene. At age 17, she married another farmer, only to grow estranged and eventually divorce him in 1984.
That man was Duane Schrock, who attained fame during the trial of the Bundy clan that took over the Malheur National Wildlife Refuge. Schrock, a supporter, testified in the trial that he felt an FBI informant had tried to pressure him into saying false things.
Cummings said her beliefs are very different from Schrock's. "I'm not anti-government in any way shape or form," she said.
She eventually got degrees in computer science, a master's in business administration and a Ph.D. in organizational leadership. She worked for the state of Montana as a disaster recovery coordinator, and then held posts for the state of Washington. In Alaska, she held a variety of jobs. She also taught at a variety of colleges in the Spokane area as an adjunct instructor.
Along the way, she has written two novels about horses. She also co-owns a race-horse with her sisters named "Mr. Jagermeister" — a name she says her younger sister, a horse-trainer, selected.
"We almost made it to the (Kentucky) derby" last year, she said. "We were very close."
Political profile unclear
Since being elected, Richardson has tried to fulfill his campaign promise and strike a nonpartisan, good-government tone. A member of the Church of Jesus Christ of Latter-day Saints, he has gone out of his way to say that his religious beliefs — Mormons consider homosexuality immoral — won't affect his job. He has promoted events focused on diversity and said he intends to represent all Oregonians.
It's unclear if Cummings completely mirrors Richardson's focus. In February, after she and Trout were hired by Richardson, the secretary of state's then-spokesman, Michael Calcagno, resigned, citing changes in top leadership at the agency, contrasting it with the "progressive way forward" he had sought for Richardson.
Calcagno did not respond to two Tribune requests for comment on this article.
But Cummings, though a registered Republican, said partisan politics don't enter her day-to-day thinking: "I don't wear a political hat, so I don't think of myself as a Republican or Democrat or whatever."
She comes from a devout evangelistic background, one that believes in the Rapture, a teaching that all Christians will be called up to heaven at a certain time. Last year, according to an email obtained by the Tribune, she emailed family and friends, including a state employee, that her research had showed the Rapture was occurring in 2017.
Cummings says her beliefs do not keep her from working for the public with the long-term view.
"As a person of faith it is my moral responsibility to work hard and do my best for all the people of Oregon, both short and long-term. No one is promised tomorrow, so that is why I live each day to the fullest," she said in an email.
Would her beliefs affect her leadership, or could she follow the middle ground sought by Richardson?
"First and foremost I'm an Oregonian," she said. "I know what it's like to not be heard when you're going through challenges. So I really appreciate (the) secretary's vision of equality for all. Equality for all is important for me ... I have some very strong feelings as trying to make sure that every voice is heard and to be an advocate so that those voices can be heard."
" I really care about all people and is why I am a public servant — that includes the LGBTQ community," she said. "I do believe God loves us all so much that He has provided a way for each of us to get to heaven."
So might she run if Richardson steps down?
"There's always," she said, then caught herself, adding she hadn't discussed it with Richardson. "I'm going to serve wherever secretary wants me to serve, period. I'm sure he thinks about that, any prudent person would. I'm sure he's formulating some sort of a backup plan, like insurance."
That plan hasn't been revealed. And on Friday Richardson's chief of staff, Royal, said he is responding well to treatment and feeling strong, and would be attending the land board.
"He is engaged and leading the agency," she added. "We are all happy and very encouraged."
That was before the news this week that Richardson would not be able to attend the land board meeting after all.