Ken Jennings's Kennections Quiz Returns With a New Brain-Teaser

Ken Jennings spent his high school years watching Jeopardy! after class, which eventually led him to compete on the show itself. In 2004, he won 74 consecutive games—a record that stood for years—and walked away with over $2.5 million. He's now the official host of Jeopardy! (since 2022) and has brought the show an Emmy for Outstanding Game Show.

But Jennings has spent the last decade working on something different: a quiz format that asks you to think in layers.

How Kennections Works

Kennections is a deceptively simple concept. You get five trivia questions. Answer them correctly, and you've done half the work. The real puzzle is figuring out what connects all five answers—the hidden thread that ties them together.

The genius is in the construction. Each question works as standalone trivia; you don't need to know the connection to answer it. But Jennings sources his themes from places like Wikipedia disambiguation pages, where single words branch into multiple meanings. A word might be a place, a person, a food, a concept—and all five answers could share that same word, or follow some other pattern entirely.

The format has gained enough traction that Jennings published The Complete Kennections in 2025, collecting his best quizzes in book form. People have been solving these puzzles on Mental Floss for years now, testing themselves on everything from history and science to pop culture and wordplay.

What makes Kennections stick is that it rewards both knowledge and pattern recognition—the ability to hold five separate facts in your mind and then step back to see what they have in common. It's the kind of puzzle that feels impossible until it suddenly clicks, and then you wonder why you didn't see it sooner.

If you want to test yourself, the latest quiz is ready. The challenge, as always, is to think beyond the individual answers.