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Rob Holland ran for Port Commission in 2009 as a promising new candidate: a progressive, with a master’s degree in public policy and a union family. He pledged to bring a middle-class voice to a board traditionally populated by wealthy business interests.

He had a well-funded opponent, but he raised money from minority business owners and unions, hired one of the state’s most prominent political consultants and, at age 35, won the seat with 56 percent of the vote.

But what seemed to be a bright political future has been clouded by myriad personal and professional problems.

Holland has run afoul of Port credit-card policies so many times he started keeping his card locked up at the Port offices. He resigned from his King County government job after county staff raised questions about two nonprofits he launched with his business partner, a convicted armed burglar and sex offender.

He bounced a reimbursement check he wrote to the Port and, six months ago, a Pierce County judge issued a warrant for his arrest after he missed a court date for driving with a suspended license. He resolved the case.

In an interview, Holland said the other commissioners and staff don’t give him the respect he deserves as an elected official. He speculates it’s because he’s young, gay and black.

“Age has a lot to do with the way these people treat me,” he said. But he says he has to overcome what he views as discrimination “or else it’s going to be a place (for) very wealthy people with a lot of experience on their hands who are interested in being international boosters. It’s for them. It’s not for us.”

Holland is proud of his work to attract women- and minority-owned businesses to Seattle-Tacoma International Airport and bring attention to human trafficking. He said he worked directly in meetings in South Korea to negotiate a lease with Hanjin, one of the Port’s largest container-shipping lines.

Despite his hard work, he said, he has not been respected.

“When I was first elected on the Commission my colleagues had their lunch brought up to them on busy Port meeting days,” he wrote in an email to The Seattle Times. “When I inquired why haven’t I received the same treatment I was told by Port staff to go downstairs and get my own.”

The Port of Seattle Commission oversees the Sea-Tac Airport, Fishermen’s Terminal, the local cruise-ship industry and the seaport, which handles about 20 million metric tons of cargo every year.

The five-member commission hires and fires the Port CEO and represents the Port locally and around the world as it competes in an international market.

Holland said he was packing for his first international trip, to South Korea, four months into his term when his suitcase broke.

He couldn’t afford to buy a new suitcase, and didn’t have time to drive to Bremerton and borrow one from his parents, he said. So Holland put $197 worth of luggage on his Port credit card, packed and boarded the plane.

That wasn’t his only improper charge: a 2011 consultant’s report found he charged at least $1,200 to his Port credit card for other personal expenses, including magazines and alcohol. The report also turned up a lewd photograph on Holland’s work cellphone.

When Port staff discovered the personal charges, they told Holland to pay them back. But when he tried, his check bounced.

The consultant looked into whether Michael Martin, Holland’s friend and former campaign manager, used Holland’s Port credit card to buy $31 worth of equipment at Fry’s Electronics for a Port-owned camera. The report described the Fry’s transaction as “potential unauthorized purchases” that were “unsubstantiated.” The transaction was documented by an invoice with Martin’s name as the customer and Holland’s credit card number.

Martin is not employed by the Port, but has worked without pay for Holland as his personal assistant, spending hours in his office, using Port phones and computers.

Holland’s hot-and-cold personality is reflected in emails obtained through a public-records request, which reveal relationships with other Port commissioners and staff members that are filled with threats, abruptly canceled meetings and accusations that he is not well treated.

Tense relationship

His relationship with the commission’s staff has been so tense that, at one point, he threatened to move out of the Port Commission offices.

When an office administrator reminded him not to rack up roaming charges on his iPad’s data plan while traveling in India in October 2012, Holland shot back, “Don’t try setting me up.”

Last fall, he emailed Port CEO Tay Yoshitani, Director of Commission Services Mary Gin Kennedy, and Port Chief of Staff Kurt Beckett that his time on the commission was “one of the most disrespectful environments I have experienced in my entire life.” He continued: “The arrogance and unprofessional way of handling me is to put it blunt — a mess. It is a mix of racism, homophobia and age discrimination.”

Yoshitani wrote back and offered to meet. Yoshitani has declined to comment about Holland, but their conversation must have helped. Shortly after, Holland wrote to the same group again:

“Please forgive me. Tay and me had a good talk.”

In an emailed response to questions from The Seattle Times, Holland said clashes with his colleagues are just part of the work. “I’m passionate about what I believe in and there have been times when colleagues and staff members have had disagreements. But at the end of the day, we work it out and the institution is better for it.”

After Commissioner Tom Albro questioned Holland’s request last fall to fund interns to serve as personal assistants to commissioners, Holland wrote to Albro to say he would not vote for the 2013 budget.

“Tomorrow’s public meeting is going to be painful,” he warned.

In other emails to Albro on the same topic, Holland said he would call the press about his remarks opposing the budget. “I hate how this will look for us,” he wrote. “But, we all adults and we make our decisions on these matters.”

In another: “Your simply isolating a fellow commissioner quietly growing in discontent, building in resolve to fight even harder in the minority making all of us look a little dysfunctional. That comes from playing chess.”

In the end, Holland voted for Albro’s budget, and Holland withdrew his intern legislation.

“Basically, we sat down together and we tried to understand each other’s point of view,” Albro said. “I’ve found Rob to be passionate and very committed to his public role.”

Holland is the commission’s most liberal member now. But he started his political career in 1999 as a Republican, working for the conservative economic think tank Washington Policy Center, where he wrote 10 papers opposing affirmative action.

Holland returned to politics after graduate school in 2005 as a Democratic Party activist, later chairing the 37th District Democrats.

That’s where he met Democratic political consultant Christian Sinderman.

“He just seemed like a nice party activist,” Sinderman said. “You know, earnest.”

Holland ended up hiring Sinderman, along with fundraiser Colby Underwood, to help him with his 2009 campaign against Bellevue real-estate broker David Doud. He still owes Sinderman “a couple grand” from that campaign, Sinderman said.

Holland told The Times that voters elected him in part because they find him “politically refreshing.”

“I am not politically
correct,” he wrote. “I tell it the way I see it. And I don’t mind saying sorry if I’m wrong. I believe in ‘gut’ politics.”

Job struggles

The Port commission stipend is only about $500 a month, and Holland has struggled to hold down a job.

In early 2009, the state issued a tax warrant against him in order to collect $663 after he overcollected his unemployment benefits.

He applied for rental assistance in the summer of 2011 because he couldn’t afford a place to live.

In July 2011, Holland started a job making $26 per hour as a temporary social worker in a King County job-placement program. The work was grant funded, helping people re-entering the workforce — veterans, young people getting out of prison — find jobs.

Two months later, he started two corporations on the side: WorkReady and the Holland Jobs Initiative.

According to a Facebook page Holland set up, the nonprofits were intended to do essentially the same work Holland was doing at the county.

“We are a private workforce development nonprofit firm fight for jobs. … Our goal is simple — Washingtonians helping Washingtonians. Neighbor to neighbor!”

A website,, is registered to Martin, Holland’s friend and campaign manager.

Holland said by email he had been interested in job-placement work since 2007, when he served on a state board. He modeled his nonprofit after a program started by Newark Mayor Cory Booker, he said.

Holland met with Steve Daschle, the executive director of Southwest Youth and Family Services, to arrange to run WorkReady from its offices on Delridge Way Southwest. Daschle said he was impressed by Holland’s description of the work, and knew he was a Port commissioner and had done similar work for the county. He agreed and set up a mailbox for WorkReady.

Daschle said he never saw Holland after his initial visit to set up office space, though Holland still listed WorkReady as his employer on campaign questionnaires last spring.

“He has a stack of mail waiting for him to pick up here,” Daschle said.

Less than five months after he started, Holland left the King County job abruptly.

Sherry Hamilton, a spokeswoman for the King County Department of Community and Human Services, said the county became aware of and had questions about Holland’s “work in the community and his work with us … because the work was similar.”

Holland quit Dec. 7, 2011, without notice, writing in his letter of resignation, effective that day: “I will always be interested in youth development both inside and outside of my employment at King County YouthSource.”

He cited his work placing people in jobs and wrote: “Rest assured, King County resources and time were used to assist these young people.”

Holland said in an interview he left because the grant funding ended. The county said the grant continued for nearly two more months.

Friend in trouble

Holland had started his outside job-placement organizations with Alik Lebedev, a friend with whom he had previously co-owned a biodiesel wholesale business, Gulf Energy.

Lebedev, 38, of Everett, is a Level II sex offender, convicted in 2006 for dealing and possessing child pornography and offering to have sex with an undercover police officer he thought was a 14-year-old boy.

Lebedev also was arrested in 2000 when he was caught using a stolen car and trying to steal $4,000 worth of rings in a burglary at the Everett Mall Sears. A store manager pretended his hand was a gun and bluffed Lebedev, crouched behind the jewelry case, into dropping his weapon.

He spent almost three years in prison for the burglary and 2½ years in prison for the sex-offense charges. He was released the second time in April 2009.

Lebedev was in trouble with the police again in 2010, when he failed to register his address when he moved. He is still on community supervision, and could not be reached for comment. A person who answered the phone at his ex-wife’s house said they were no longer in touch.

Holland said he doesn’t remember how he met Lebedev, who became an executive in Holland’s company, Gulf Energy, and president of his two nonprofits.

In an email, Holland wrote: “My relationship with him is an entirely private matter and should remain one. I was unaware of his criminal background and only recently was it disclosed to me.”

Holland said he cut ties with Lebedev when he learned about his criminal history.

“I don’t know nothing about him anymore. … He’s gone,” he said, adding it made him angry even to hear Lebedev’s name.

Holland said he shut down the two jobs programs because of lack of funding. He said he is now working for his dad, managing investment property.

Foreign-service hopes

Holland’s term is up at the end of this year.

In his run last year for state representative in the 11th District, Holland was endorsed by former King County Executive Ron Sims, four members of the Seattle City Council, state Sen. Ed Murray and other prominent local officials, as well as big labor organizations. He lost in the primary.

On Tuesday, he is taking the foreign-service-officer exam, and hopes to become an ambassador, he said.

Asked recently whether he plans to run for a second term on the Port Commission, Holland started crying.

“I’ve found this to be very disappointing,” he said. “I’m trying not to tear up about it. I’m elected to do a job. … I really thought this was an opportunity to do that, and it’s really tough.”

News researcher Gene Balk contributed to this report.

Emily Heffter: 206-464-8246 or