THE MATERIAL IS WRITING ITSELF. WE JUST NEED YOU TO ILLUSTRATE IT.

The Rutabaga Invites You to Skewer the Powerful, Embarrass the Shameless, and Win a Prize Doing It

AI generated political cartoon designed by David Rubin

---

YOUR TURN: The Rutabaga’s First Political Cartoon Contest

(For the uninitiated, The Rutabaga is our version of The Onion)

So here’s how this started.

I’ve been using AI image generators to produce the cartoons you’ve been seeing on this Substack — prompting, tweaking, arguing with the algorithm, the whole thing. Apparently that inspired one of our readers, David Rubin, to try his hand at it and send one in (see above). And honestly? It was damn good.

Which got me thinking: why should I have all the fun?

So we’re doing this. The Rutabaga’s First Political Cartoon Contest — open to anyone who wants to take a shot at it.

The Rules (such as they are)

Pick a news story. Pick a target — the Trump administration, a cabinet member, a member of Congress, whoever or whatever has earned it this month. Then use any AI image tool, pencil, pen, iPad, or drawing program you like to design a political cartoon that captures the moment. Prompt it, sketch it, refine it, make it sing (groan, whine, or complain).

As they say, whatever floats your boat (except in the Strait of Hormuz, of course).

When you’ve got something you’re proud of, send it to larry@enlightenedcynic.com. Be sure to add your name, any caption, AI used, and email address.

The Deadline

All submissions must be received by June 12, 2026.

What Happens Next

After the deadline, I’ll post every submission in a Substack post for the full Rutabaga readership to weigh in on. You’ll have a couple of weeks to let me know which cartoon you think best skewers the powerful, captures the absurdity, or just makes you laugh the hardest. The winner gets posted in a place of honor — and the prize?

We’ve established that the news is writing its own punchlines these days. All you have to do is illustrate them.

Get to work.

FTS

Join us on our podcast the Enlightened Cynic, where satire meets substance and storytelling sparks civic engagement. Each episode dives into topics like authoritarianism, political spectacle, environmental justice, humor, history and even fly fishing and more—layered with metaphor, wit, and historical insight. We feature compelling guest interviews that challenge, inspire, and empower, especially for senior audiences and civic storytellers. Listen to the audio on all major podcast platforms, watch full video episodes on YouTube, or explore more at our website.

Let’s keep the conversation sharp, smart, and unapologetically bold