• Born in Los Angeles, CA
  • Attended Van Nuys High School Performing Arts Magnet
  • BA from Occidental College in Los Angeles
  • Moved to Seattle in November 1993
  • Developed a career in the wine industry finishing as District Sales Manager (Western WA & OR) for Kobrand Corporation.
  • Moved to Orcas Island in October 2010
  • Managed the Wine Program at Inn at Ship Bay.
  • Currently work as the Customer Service and Shipping Manager for

My Story

Photo of Cindy Wolf and her daughter in front of the ocean.

I was born in Los Angeles, CA.  My father is a West Point graduate and was in the army  when he met my mother.  She was at San Jose State. They shared a sense of duty to work for what you believe in, the value of good character, of leadership, and adherence to the idea that working alliances depend on trust built through promises kept.

I earned a bachelor’s degree at Occidental College in 1989. At Occidental I co-founded the first women’s center on campus and participated in the effort to persuade Occidental to divest its South African investments during the apartheid era. I also did AIDS education. After graduation I did community organization work in northeast L.A.

While working in the Theater Department, I met my husband, Keven McKenney.  He grew up near Gig Harbor, WA.  Trained as a physicist, he works as an electrical engineer at Northwest Marine Technology.  Our daughter, Juliette, was born in 2008.  Keven took two years off to stay home with her while I supported us as a District Sales Manager for Kobrand Corporation, a wine importer and distributor.  My job was key accounts management and local distributor sales force support and education for western Washington and Oregon.  During those years I also volunteered to coordinate the wine auction portion of the annual USO fundraiser in Seattle. 

In 2010 we decided to switch roles in the family.  We moved to Orcas Island from Seattle and ultimately bought a house in Deer Harbor.  Juliette will be starting 8th Grade at Orcas Island Middle School in the Fall.  I currently work as Customer Service and Shipping Manager for MindPlace Company, on Orcas Island.

Since coming to Orcas I have served the community by sitting on the board of directors for Children’s House, teaching civics at the Orcas Island Public Library and at the Friday Harbor Grange, taking shifts at the Severe Weather Shelter, volunteering at my daughter’s school, occasionally helping out with Orcas PTSA Roller Skating nights and at Emmanuel Episcopal Church. Most recently, I wrote a grant to Orcas Island Education Foundation and spearheaded the organizing of a combined trip to the WA State Legislature for the 8th grade class at Orcas Middle School and the 7th grade class at Salmonberry. The trip was a great opportunity for bipartisan support so the local Democrats and Republicans contributed funds.

I am running for County Council to meet the future with a good plan in place. That means more than a list of projects generated in reaction to current circumstances. When my daughter has children, I want them to be able to look around the islands and know that I was thinking of them when I cast my votes.

But we have practical challenges to meet, especially around housing. We must find ways for working islanders to buy affordable homes. We live in a beautiful place the world wants to visit. We need to house seasonal workers to staff our tourist-dependent small businesses. But we must receive tourists in ways that keep our rural lifestyle intact.

I am running to ensure your tax dollars are carefully spent, with the future in mind. Public spending should be in the public interest, to improve our environment, and our island quality of life. I want to make certain every penny we spend takes our carbon footprint, our future climate, and our economic health into consideration.

For the past three years I have served as Vice Chair of the San Juan County Democratic Central Committee, working to make sure all the voices in the room get heard. In 2017 I helped found Orcas Women’s Coalition. We have worked together to pass several school levies, draft a county ordinance, and elect some wonderful candidates who now serve as state legislators, judges, and port commissioners.

I look forward to meeting as many of you as I can and I hope you will consider voting for me.