Judge Judy Spars With Bill Maher Over Michael Bloomberg 2020 Run

Judy Sheindlin (Judge Judy) and Bill Maher - Getty - Split - H 2019
Gary Gershoff/WireImage; Vivien Killilea/Getty Images

Judy Sheindlin and the late-night host disagreed about the importance voters invest in public service experience and wealth: "There's nothing wrong with...realizing the American Dream."

Judy Sheindlin, aka Judge Judy, showed up to Real Time With Bill Maher on Friday night to argue for her 2020 Democratic candidate of choice, Michael Bloomberg.

Her advocacy for the late entrant into the presidential race ran in stark contrast to host Maher's skepticism, and the two engaged in a lively debate about Bloomberg's merits and shortfalls during their conversation. 

Maher says he initially didn't know why Sheindlin, who suggested she watches Real Time every week, was appearing on his show when she'd booked her appearance a few weeks ago. After news broke Friday that Bloomberg had submitted paperwork to run in Alabama, Maher says he understood. Sheindlin, after all, endorsed Bloomberg in mid-October, before he was even in the race.

"Michael Bloomberg is the only one, and I'm going to tell you why," Sheindlin began her pitch. "If you think about it, Michael Bloomberg is the only one who's running who has executive experience running the biggest city in the United States."

Maher, however, wasn't taking it. "Who cares?" he said.

"That's experience," Sheindlin continued. She then launched into an analogy about doctors, which Maher also rebutted.

"That's not how people think about politics," he added. "People vote with their gut."

Later, she said that when Bloomberg was mayor of New York City, "the schools were better, you felt better in the city, there was a calm in the city."

To that, Maher argued that Bloomberg might be appealing to cosmopolitan voters, but that he filed necessary campaign paperwork in Alabama and "I don't see a big-city Jew exciting Alabama." The Democratic presidential candidate would need to win Wisconsin, Pennsylvania, Michigan and Florida, he said.

Further, Maher added, Sen. Elizabeth Warren has seen success in the polls talking about the wealth gap in America, whereas Bloomberg is a billionaire businessman who didn't represent as big of a change from President Trump. "There's nothing wrong with a man that came from [nothing] realizing the American dream. I realized the American Dream," Sheindlin contended. "What I'm telling you, nothing is impossible. To define Mike Bloomberg [just] as a billionaire is an injustice." 

Maher eventually succeeded in turning the conversation away from Bloomberg, briefly, to discuss how Sheindlin was a part of the "Silent Generation" alongside Bloomberg and fellow 2020 candidate Joe Biden. "I see why they're called Silent, I forgot about it. What's the Silent Generation?" he asked her.

"I don't know, I've never heard of me referred to as silent," Sheindlin joked.

Sheindlin's endorsement of Bloomberg marked the family court judge's first-ever political endorsement. Sheindlin has said little about current President Trump in the past but did offer advice to Trump during his campaign: that he should "tone it down." In her USA Today opinion piece announcing her Bloomberg endorsement, she added that America had become "fractured" and "bitterly divided."

"I realize I am taking a personal and a career risk in making such a statement. I have carefully stayed away from politics for 50 years, except to vote. But times have changed in our country, and I believe the moment has come for me to step out from behind the curtain," she wrote.