This week, ‘Jeopardy!‘ host Ken Jennings took a break from delivering clues as he offered a political endorsement via liberal-leaning social media platform Bluesky.
In his post, Jennings declared that whichever 2028 presidential candidate promises to “prosecute the former regime at every level” already “has [his] vote.” Indeed, he didn’t name President Donald Trump directly, but given the current political climate and controversies surrounding Trump’s administration, we all knew exactly what he meant.
On Jan 7, a woman was fatally shot in Minneapolis during an ICE encounter. That context played into Ken Jennings’ view, clearly. Critics have been accusing the ICE agent of using excessive force, too. The Department of Homeland Security has labeled the incident an act of “domestic terrorism,” as they say the now-deceased woman targeted an agent with her car.
Ken Jennings is 🎯. The only way this happens though is if you get rid of the old timey leaders like Chuck Schumer & Hakim Jefferies. Need more aggressive angry leaders & a Pitbull AG to make this happen. Also, Elon Musk needs to be reigned in before 2026 midterms. pic.twitter.com/19T62mkLzv
— Lor (@LorX0X) January 8, 2026
For longtime Ken Jennings fans, the post was not entirely surprising. A 74-time “Jeopardy!” champion, he has occasionally ventured into political commentary, sometimes drawing criticism from conservatives. He also became the solo host of the iconic quiz show in 2023.
Before the viral 2028 comment, Jennings mocked U.S. policy on Venezuela by comparing regime-change efforts to failed New Year’s resolutions, a joke that carried a clear ideological tone.
It is also worth noting that Jennings endorsed Bernie Sanders and Elizabeth Warren during the 2020 Democratic primaries. At the time, he joked that the “defending champion” wanted their votes. Even earlier, he faced significant backlash over a 2017 tweet about Barron Trump, which he later deleted after many said his dark humor crossed a line. Jennings initially defended himself but later apologized for his “unartful and insensitive” past tweets.
That controversy resurfaced in December 2020, as Ken Jennings was being considered to succeed the late Alex Trebek. After years of questionable jokes, he acknowledged that what sounded clever in his head often read poorly and said he was “truly sorry” to those he had hurt.
But does Jennings’ latest comment suggest he is no longer interested in playing it safe?
That time Ken Jennings called Alex Trebek a “Boomer.”
(01/09/2020) pic.twitter.com/4uoLu5V3tM
— The Millennial Snowflake 🇵🇸 (@Teh_Snowflake) January 31, 2024
On Bluesky, users reacted with the familiar rhythm of “Jeopardy!”-style questions and dollar amounts. Jennings even replied to one critic, saying he did not want people “shot at their kitchen tables,” though that response quickly reignited the broader debate over whether celebrities should weigh in on politics at all.
According to a YouGov survey, only 7 percent of Americans say a celebrity endorsement influences their vote. However, more than half say they have formed a negative opinion of a celebrity because of that person’s political views.
At the same time, figures like Ken Jennings carry a certain intellectual credibility with audiences. While his comments are unlikely to sway elections, neither Sony Pictures nor Jennings’ representatives have responded publicly to his remarks.
