Charles Gilcrest, the long-time political consultant and local insider who helped start the political careers of many San Leandro elected officials, and later served as informal advisors for several mayors and councilmembers, died on Monday. He was 64.

Gilcrest was serving the last year of his first term as a board director on the Eden Health District at the time of his death. Gilcrest passed away after complications that followed after suffering a heart attack last week.

The world of politics is known to be dirty place, but Gilcrest’s nearly five decade-long participation in San Leandro struck a notably positive tone. As a consultant, he helped guide many of the city’s up-and-coming future leaders into local office. A consummate insider who often eschewed the limelight, Gilcrest was a guiding force to move San Leandro away from its history of racial segregation through the removal of decades-old housing covenants that once prohibited minorities from purchasing homes in the city.

“Charlie deeply loved San Leandro. He treated the city as his family, devoting countless hours to the people of San Leandro,” former San Leandro Mayor Stephen Cassidy said.  “He was a person of integrity who acted always in the best interests of the community. Charlie had a brilliant mind and gentle nature. Charlie used his gifts to make our city and the Eden Area better.”

“Charlie Gilcrest was a kind-hearted soul,” said Ellen Corbett, former San Leandro mayor and member of the state Legislature. “He was generous, sharing his political wisdom and his positive outlook freely.”

Gilcrest’s political activity also included serving on a host of San Leandro boards and commissions, in addition, local Homeowners Association boards.

A product of San Leandro, Gilcrest graduated from San Leandro High School, where he once ran for school president, and later from U.C. Berkeley, where his political activism began to evolve. During his time at Cal, Gilcrest embraced the idea of Ranked-Choice Voting in local elections, and advocated for then-Mayor Tony Santos to bring it to San Leandro in 2010.

The breadth of Gilcrest’s historical knowledge of San Leandro’s politics over the past five decades is unquestioned, seemingly pulling anecdotes out of thin air linking the city’s rapid expansion under Mayor Jack Maltester through the rise of Ellen Corbett to the present.

In 2016, he attained his life-long goal of serving as an elected official after winning a seat on the Eden Health District. As local and state officials  made attempts to dissolve the health care district during Gilcrest’s tenure, he helped steer the board through uncertain times that followed the district’s loss of San Leandro Hospital.

Gilcrest, along with the current Eden Health District board, is credited with bringing a covid-19 testing site to San Leandro earlier this year.

“Charlie brought passion, energy and foresight to the Eden Health District Board. We will greatly miss his leadership and empathy for the underserved,” said Gordon Galvan, chair of the Eden Health District Board of Directors.

Despite declining health in recent years, Gilcrest continued to maintain a consistent presence, not only at Eden Health District meetings, but San Leandro City Council and Alameda County Democratic Central Committee meetings.

Gilcrest was selfless to his core, said Chris Gray, a long-time friend and fellow East Bay political consultant. In 2008, Gilcrest attempted bid for the San Leandro City Council that proved unsuccessful. Gray recalls Gilcrest spending more time working for another candidate in a different race than his own council campaign. “That’s who he was. The reason he had some friend is he was always there to help people. He never really said anything bad about anybody,” Gray said.

During a candidates forum for his 2008 council run, Gilcrest explained his view of public service and his affinity for San Leandro. “I’ve tried to be active in this community and I’ve tried to give back,” he said. “And I see so much potential in this city.”