Two prominent Democratic figures with deep ties to the Clinton and Obama administrations publicly criticized New York City Mayor Zohran Mamdani this week, with former Clinton adviser Mark Penn attacking the mayor’s proposed property tax plan while former Obama White House chief of staff Rahm Emanuel recounted what he described as a private conversation in which he challenged Mamdani’s rhetoric on Israel.

The criticism is notable because it comes from longtime Democrat insiders rather than Republican opponents and focuses on two of the issues that have defined Mamdani’s rise political rise: his far-left economic agenda and his positions on Israel.

Fox News Digital reached out to Penn, Emanuel and Mamdani’s office for comment.

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Penn, a longtime Democrat strategist and former pollster and adviser to President Bill Clinton, accused Mamdani of dramatically understating the scope of his proposed pied-à-terre tax after the mayor released a public database identifying property owners who could be subject to it.

In a lengthy post on X, Penn argued the city’s valuation system had swept in nearly one million property owners rather than the roughly 30,000 luxury homeowners Penn said had previously been described as the intended targets.

“The $5 million figure was a fake,” Penn wrote, arguing the city’s valuation system had improperly classified properties and would force homeowners to prove they should not be taxed.

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Former Mayor of Chicago and White House Chief of Staff Rahm Emanuel speaks during the 29th annual Milken Institute Global Conference at the Beverly Hilton in Beverly Hills, California on May 5, 2026. ((Photo by Patrick T. Fallon / AFP via Getty Images))

Penn also argued the proposal could depress property values, discourage investment in New York City and potentially raise constitutional questions.

Meanwhile, Emanuel said during an appearance on the Unholy Podcast that he met privately with Mamdani for roughly 90 minutes and challenged the self-described democratic socialist mayor over his views on Israel.

Emanuel said he praised portions of Mamdani’s domestic agenda, including childcare, but criticized Mamdani’s past use of the phrase “from the river to the sea.”

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New York City Mayor Zohran Mamdani’s video admitting that he lacks the legal authority to arrest Israeli Prime Minister Benjamin Netanyahu did little to ease Jewish leaders’ concerns. (NYC Mayor’s Office via YouTube/Handout via Reuters)

“I know where there’s a line. You don’t,” Emanuel recalled telling Mamdani.

Emanuel said both calls for a “Greater Israel” and the slogan “from the river to the sea” would lead to “perpetual conflict.”

After clips of Emanuel’s remarks circulated online, Mamdani communications director Anna Bahr publicly disputed the account.

“can confirm this …. did not happen,” Bahr wrote on X in response to a post summarizing Emanuel’s remarks.

It was not immediately clear from Bahr’s post whether she was disputing that the meeting occurred or Emanuel’s characterization of the conversation.

Emanuel has also recently criticized the Democratic Socialists of America (DSA) more broadly. In a post on X this week, he argued Democrats should focus on winning competitive elections rather than what he characterized as ideological distractions.

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“You can be focused on winning tough races, flipping red seats blue. Or you can be focused on abolishing prisons and… the Senate and Supreme Court? You can’t do both,” Emanuel wrote. “I’m for winning this November and ending Trump’s corruption — and I’m also for putting an end to all the distractions from the DSA.”

Penn, Emanuel and Mamdani’s office did not immediately respond to Fox News Digital’s requests for additional comment before publication.