How a $100 ‘Jeopardy!’ Bet Caused a Rift Between Howard Stern and a Member of His Staff

Howard Stern has a bone to pick with longtime Stern Show staffer Jon Hein.

During Tuesday's episode of SiriusXM's The Howard Stern Show, the radio host detailed an unsettled bet between him and Hein involving Jeopardy! and its host Ken Jennings.

"We had a bet," Stern recalled. "I said, 'Jon, there is no way Ken Jennings is going to be the host of Jeopardy!.' And Jon said, 'I'll bet you a 100 bucks.' And I said, 'Fine.' Turns out Ken Jennings and Mayim Bialik, they were chosen together in tandem. He was not the host, he was the co-host."

"When this happened, they tried a bunch of different people, and I said that Ken was going to be the host, which you disagreed with," Hein told Stern.

"Ken was always the full-time host," Hein added.

"It's not like Mayim Bialik was fired or deselected, she stepped away because of the writers' strike, and now they've decided that Ken is the permanent host," co-host Robin Quivers chimed in. "The bet has to end at some point."

"It's not about the $100, it's about the fact that Ken Jennings … he's always had the job," Hein added.

"If four years from now Ken Jennings is not the host, do I get my money back?" Stern asked.

When executive producer Gary Dell'Abate pointed to a 2021 article reporting Mike Richards and Bialik as the permanent co-hosts, co-host J.D. Harmeyer ended the debate.

"In that case, the evidence goes towards Howard," he said.

"I don't want [the money] — send it to charity," Stern said.

When the trivia show's longtime host Alex Trebek died in 2020, Jennings was the first to take over, and he was joined by former Big Bang Theory star Bialik to split their hosting duties shortly afterwards. However, on Dec. 15, Bialik announced that she would not be returning to host the syndicated show nor its primetime specials.

"It took me off guard, because I loved working with my Mayim and I'm gonna miss her. I can't speak to her decision-making process or her opinions about it," Jennings told the Hollywood Reporter in an interview published in December. "But on my end, I'm just a fan of Jeopardy! and I'm always delighted to host when they call upon me. I just feel extremely lucky to have even been considered for this job as a non-broadcaster."

Jennings also shared that it was "weird" to come back as a host after being known as a contestant on the series for so long, but he's been doing his best to learn "as I go."

"But I loved growing up with Jeopardy! where Alex was the host of that show for almost 38 years, and people just kind of felt like he was part of their family, and it's impossible to fill those shoes," he added. "But it's such an honor and hopefully I look forward to 37 more years of doing it, when I'll be a very, very old man."