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Activist Rebecca Sive, who had ‘deep passion for social change and civil rights,' dies
Longtime Chicago political activist and author Rebecca Sive's passion for advocacy and desire for social change led her to organize for the American Jewish Committee and co-found and lead the Midwest Women's Center.
Sive also worked on the campaign of the late Mayor Harold Washington, who, after winning election in 1983, appointed her to the Chicago Park District Board of Commissioners. She was also executive director of the Chicago-based Playboy Foundation.
'To find someone who has a deep passion for social change and civil rights and personal freedoms who is also entrepreneurial in their ability to found and run an entity is not that common,' said former Playboy Enterprises Chairman and CEO Christie Hefner. 'Rebecca was equally right-brain and left-brain — she could be highly creative and then also highly organized and attentive to detail.'
Sive, 75, died of heart failure on July 15 at Corewell Lakeland Hospital in St. Joseph, Michigan, said her husband of 53 years, Steve Tomashefsky. A Keeler, Michigan, resident since 2020 who previously had lived in Lakeview and then the Gold Coast, Sive suffered a massive stroke in September 2023 and had battled back to speak, her husband said.
Born in New York City, Sive was the daughter of a writer and editor mother, Mary Sive, and an environmental lawyer father, David Sive, who ran unsuccessfully for Congress in 1958. As a toddler, Sive moved with her family to Pearl River, New York, where she grew up.
After graduating from Pearl River High School, Sive earned a bachelor's degree in urban studies in 1972 from Carleton College, where she and several classmates found success in political organizing when they lobbied leaders to establish women's health services on campus. Sive's faculty adviser was then-Carleton professor and future U.S. Sen. Paul Wellstone. During college, Sive studied in Chicago for a semester on the Associated Colleges of the Midwest's Urban Studies program.
Sive settled in Chicago after college and organized a collective of four women to research, write and publish 'The Chicago Women's Directory,' a book published in 1974 that provided detailed lists of services and opportunities for women across Chicago's neighborhoods. Sive, who oversaw the marketing of the book, concurrently earned a master's degree in American history from the University of Illinois at Chicago.
Sive worked for a time as a community organizer for the Institute on Pluralism and Group Identity of the American Jewish Committee. In 1977, Sive co-founded the Midwest Women's Center, a grant-funded advocacy group focusing on women's issues, including training women for traditionally male jobs, such as construction and auto repair.
In 1979, Sive coordinated the creation of 'The Illinois Women's Directory,' a guide with the same kinds of information found in the Chicago directory.
'We received so many phone calls from all over the state that we knew we had to do a statewide directory, not one just for Chicago,' Sive told the Tribune in 1979.
In 1981, the Playboy Foundation — Playboy's activist grant-giving arm — hired Sive as executive director. The foundation had long been known as being willing to support controversial issues.
'I think one of the reasons why the work that we did together was so satisfying and successful is it gave her a big sandbox to play in with all these interests,' Hefner said.
Sive went on eventually to expand her work for Playboy to include overseeing all corporate public affairs.
While at Playboy, Sive worked on Washington's successful 1983 mayoral campaign, co-chairing his women's committee, advising Washington on women's issues and organizing many fundraising events for his campaign. One of the fundraisers she arranged was at the Playboy Mansion in Los Angeles.
'It's pretty clear that the most fulfilling time of her career was working for Harold Washington,' Tomashefsky said. 'That was an exciting thing — she had high-level access, and she was by far the youngest person involved on the 'Women for Washington' committee.'
Cleo Wilson, the retired executive director of the Playboy Foundation, called Sive's work on the Washington campaign 'a big deal for her, for the company, for me, for Christie Hefner — for all of us.'
During Washington's two campaigns for mayor, she met future Cook County Board President Toni Preckwinkle.
'She was passionate about politics and public service,' Preckwinkle said.
After taking office, Washington appointed Sive to the Chicago 1992 World's Fair Authority board, where she was vice chair. Washington then tapped Sive to serve on the board of the Chicago Park District, and aldermen confirmed her nomination in July 1986.
Sive joined the park board shortly after Washington's ouster of longtime parks Superintendent Edmund Kelly. While on the board, she was part of a committee that in 1987 won approval for its recommendation to move the annual Air and Water Show to North Avenue Beach from its longtime location along the shoreline from Grand Avenue to Oak Street Beach.
Sive remained on the park board during Washington's reelection to a second term in 1987. She resigned from the Park District Board in a surprise announcement in September 1988, citing the press of business from her day job.
In March 1986, Sive left Playboy to start her own consulting firm, the Sive Group, which helped nonprofit groups with policy development, public relations and fundraising strategies. Clients included the city of Chicago's department of health, Jane Addams Hull House Association, the NAACP Legal Defense and Educational Fund and the YWCA of Metropolitan Chicago.
Sive mentored dozens of young women who worked for her, her husband said. She also served on numerous boards, including Parkways Foundation, the Chicago Foundation for Women and the Chicago Commission on Women's Affairs.
In 2000, Sive scaled back her consulting work from managing four or five employees to working as a solo practitioner. The shift occurred as she and her husband moved from West Lakeview to the Gold Coast, where she had an office in her home. She ran the Sive Group for another 15 years or so.
Sive also taught a class on women in politics at the University of Chicago Harris School of Public Policy, where she was an adjunct professor from 2012 to 2015.
'She was a feminist (and) she really wanted to make a better world for women,' Wilson said.
In 2013, Sive authored her first book, 'Every Day Is Election Day: A Woman's Guide to Winning Any Office, from the PTA to the White House.' She published 'Vote Her In: Your Guide to Electing Our First Woman President' in 2018, providing what effectively was a manifesto to elect a woman to the highest office in the land.
'Revolutions don't happen overnight,' Sive wrote in the book, 'and every day presents a new chance to act, to share messages that resonate, and to model behavior that will mobilize other women.'
Sive's final book, 'Make Herstory Your Story: Your Guided Journal to Justice Every Day for Every Woman,' was published in 2022.
'It doesn't matter where you come from, where you live, what your age is … we all can be a part of doing good, helping other women,' Sive told the Tribune in 2022 in an interview about the book. 'I think the key to successfully writing it down in a journal, and then acting on it methodically is to stay focused. It doesn't matter what the issue is, it doesn't matter what neighborhood it is. Find an issue that will mobilize the broadest number of people, and as we come together and hopefully succeed on that issue, is there another one we can take on? Systemic change is groups of people coming together and individuals affirmatively deciding: We're going to do this together.'
As part of her second book, Sive hosted a podcast, '#VoteHerIn,' from 2019 until 2021, in which she interviewed numerous female politicians, including Preckwinkle, U.S. Sens. Amy Klobuchar and Debbie Stabenow and U.S. Rep. Jan Schakowsky.
'Rebecca was a tireless advocate for women in particular,' Schakowsky said. 'There's not really a comparable voice (now) — all of us do our best — but she was so special and so tireless in her work.'
Sive was a longtime enthusiast of Chicago blues and gospel music, dating back to when she was in her 20s, her husband said. She was also an avid ceramics collector, amassing a large collection of work by both noted and emerging ceramists that was featured in American Craft magazine in 2019.
Sive also enjoyed traveling in Brazil, south Louisiana and the Mississippi Delta. After moving to Michigan in 2020, she took a great interest in gardening.
In addition to her husband, Sive is survived by a sister, Helen Paxton; three brothers, Alfred, Walter and Theodore; a nephew; and five nieces.
A memorial service is being planned.
