IN MEMORY OF ROBERT L. SIMPSON
(August 5, 1947 - November 18, 2023)
ACTIVIST, CARTOONIST, TEACHER, BLOGGER, PHOTO JOURNALIST
MEMORIAL ON SATURDAY, AUGUST 17TH, 2024
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Robert L. Simpson, fondly known as "Bobbo," passed away on November 18, 2023, at the age of 76. Born in Washington, D.C., Bob's journey through life was one of passion, activism, and creativity. He moved to Chicago at the age of 26, where he left an indelible mark on the communities he served and inspired.
Memorial service will be held in Spring 2024.
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He is survived by his wife Estelle Carol; two children Dana and Colin; a sister Sheila Chapelle and a brother Craig Simpson. We are planning a memorial event for the spring.
Estelle created this website as a memorial to Bob’s many talents, energy, creativity and generosity. Please send comments, stories and memories to Estelle at ecarol[at]webtraxstudio.com so she can add them to the website. Please call and send text messages to Estelle at 708-616-6473. If you send her an email please, alert Estelle with a text message.
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Bob graduated from Springbrook High School in Montgomery County, MD where he served two years on the “It’s Academic” team, and from the University of Maryland College Park with a BA in English Literature, Secondary Education. He later attained an MA in Urban Education from Catholic University and an MA in History from Northeastern Illinois University.
He was influenced by the Beat Generation and the folk music revival of the early 1960s. At the University of Maryland at College Park, he played a leading role in the Students for a Democratic Society chapter on campus.
After graduating from UMD, he was hired as a teacher in the District of Columbia schools where he taught at Roosevelt High School and the old Western High School. During that time he continued to be active and did support work for the local chapters of the Black Panther Party and the Patriot Party. He also continued to play a support role for antiwar activists at College Park and was part of a local group called the Mother Bloor Collective.
In 1973, he was part of the Venceremos Brigade, American activists who went to Cuba to do sugar cane harvesting and other types of work in solidarity with the socialist country. It was on the Cuba trip that he met his future wife, Estelle Carol, and ultimately moved to Chicago where she lived.
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In Chicago, Simpson and Carol formed a partnership that published a comic-book style history of the United States (The Incredible Shrinking American Dream”) viewed through a radical lens.
The two also produced hundreds of cartoons under the Carol Simpson CartoonWork moniker for union, educational, business, alternative, activist, environmental and academic publications. Simpson wrote the gags and Carol created the cartoon illustrations. The cartoons are known for being strong supporters of the labor movement, aiming to motivate people to question socio-economic systems and support an educated, diverse, and well-organized working class movement.
Carol and Simpson wrote: “We hope that our cartoons motivate people to question our dysfunctional socio-economic system. We are strong supporters of the labor movement, which for all of its blemishes, is the most diverse social movement in the USA today. We will only create a more humane world if there is an educated, democratic, diverse and well organized working class movement to do the job.
Carol is currently designing a Carol Simpson CartoonWork archive website with 800+ cartoons created between 1985 and 2015. View some cartoon at Cartoon Movement.
For example, the cartoons appeared in Substance newspaper led by George Schmidt who challenged both the Chicago teachers union and the Chicago Public schools around issues like racism, segregation, working conditions and emphasis on standardized tests. This laid the groundwork for CORE (Committee of Rank & File Educators) which under Karen Lewis transformed the CTU union into a political force leading to the election of the current Chicago mayor.
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Simpson initially worked as a training specialist for adult learners at the City Colleges of Chicago before teaching for 15 years in the Catholic school system in Chicago. He later concentrated on the business end of their home-based graphic design and website development company, WebTrax Studio. He also wrote for his own blog “The BobboSphere” and contributed regularly to the Daily Kos and other online publications.
Simpson was a visible face on the Chicago left, attending hundreds of demonstrations. Later in life he began chronicling them through photographs that he provided free to the sponsoring organizations and individuals.
He was a member of several labor unions through his career, including AFSCME Local 1072; Washington Teachers Union Local 6, AFT; and the National Writers Union.
He was arrested several times for his activism, including inciting-to-riot while protesting presidential candidate George Wallace at Capital Plaza in Maryland and in Chicago during the Occupy movement. All charges were later dropped by authorities.
Although his activism was cut short by a stroke in 2016, but he continued to contribute to the cause through Facebook and other social media musings.
Have photos Bob you’d like to share? We’d love to see them. Send Estelle an email at ecarol[at]webtraxstudio.com







