Drawing Laughs, One Politician at a Time

Bill O'Neal drawing cartoons at a desk.

Bill O’Neal held many titles over a 60-plus-year career: Technical writer, Air Force operations analyst, advertising executive, marketer, and business owner, among others.

However, it’s work as a cartoonist that has brought the 84-year-old Sturges Ridge of Fairfield resident the most professional and creative satisfaction.

While it never paid the bills, he says, creating political cartoons or “gag” cartoons has been a constant creative outlet throughout his life. He has a portfolio large enough to fill three self-published books featuring his single-panel cartoons spanning decades of U.S. politics and history – from the tumultuous 1960s to present day.

“The hardest part is finding something funny about a topic. Some are just not funny. Hopefully, the cartoon pulls in the reader and the caption pays it off,” explains Bill, who moved to Sturges Ridge in 2021 following the death of his wife, Dian.

Bill is an active member of the community and well-known to the residents and staff. When he is not socializing, you can find Bill in his apartment drawing humorous – often biting – cartoons about politics of the day. His work is published in each issue of a newspaper in California, where he used to live.

Bill says it’s not about earning money but resuming a lifelong passion.

As a biochemistry major at Purdue University, Bill worked at the school’s humor magazine where he fell in love with cartooning. “That was fun! I became editor to ensure that I could get my cartoons published,” he said, laughing.

A biochemistry career was soon out the window, Bill says. Instead, he wanted to create cartoons for newspapers and magazines. He understood, however, that cracking into such a highly competitive profession would be difficult and he needed something to fall back on. After college, he sold ad space for Time Life in Chicago, then became a technical writer, and later joined the military.

It was serving in the Air Force in Chicopee, Mass., that he got his first break. He found military work as an operations analyst fascinating but the job also had a normal schedule, allowing him to take a freelance cartooning gig at The Springfield (Mass.) Republican.

“I now had this platform. The only problem I had was keeping the Air Force from knowing about it. Being the military, they were very conservative and would not have liked the topics of my cartoons,” he said.

After serving his four years in the military, Bill focused on advertising as a profession and earned a marketing degree from the University of Michigan. Soon after, he moved to New York City, the hub of the ad world.

“I wanted to become a copywriter, but the company said, ‘No, you’re going to be a suit.’ The suit is the person who sells the idea of the ads to the clients,” he explains.

The “suit” did well in the industry. He moved up the ranks and along the way made a key hire: A talented copywriter who would become his wife. He and Dian left the Big Apple in the ’70s to move to Connecticut, where Bill bought into an ad agency in Hartford, called O’Neal & Prelle. In 1994, Bill started another company, O’Neal Strategy Group, where he remains active.

In 2008, the semi-retired couple decided to move to Sonoma, California, following one of their three sons.

While at a party in Sonoma, Bill was approached by the editor of the Sonoma Index-Tribune. The editor was looking for a new political cartoonist. Bill jumped at the opportunity.

“It was a great time to start: It was the run-up to the 2016 election. Hilary and Donald were great to poke fun at,” he recalls.

Bill’s cartoons from that period led to “Race for the White House,” his second of three books. The other two focus on the 1960s and the Trump presidency.

While in Sonoma, Dian’s health began to fail. Smoke from California’s wildfires contributed further to her breathing problems and several times the couple needed to evacuate their home. They decided that they would return to Connecticut to be closer to one of their sons and his family. Sadly, Dian passed away before moving back.

Bill says he feels at home at Sturges Ridge and stays busy. He serves on the resident council, helps run the resident-operated store, and has contributed drawings to the community’s art gallery.

Bill’s not sure how many of his neighbors are aware of his cartooning, and talking politics can get messy as many people’s political views are very personal.

For Bill, as a professional lampooner, either side of the aisle is fair game. His goal?

“I strive for a laugh,” he explains. “Or at least a smile will do.”

Sturges Ridge of Fairfield