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Home»Politics»The art of dealing with Trump
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The art of dealing with Trump

September 21, 2026No Comments8 Mins Read
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Mayor Zohran Mamdani will meet with President Donald Trump at Gracie Mansion this afternoon.
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ALL EYES ON GRACIE: Mayor Zohran Mamdani is expected to sit down with President Donald Trump at Gracie Mansion this afternoon, their third in-person meeting in less than a year and the latest wrinkle in one of the strangest relationships in American politics.

Since Mamdani’s first, shockingly cordial meeting with Trump at the White House last November, political observers have scratched their heads about the democratic socialist mayor playing nice with the Republican president despite their deep disagreements on … just about everything. Ostensibly, Mamdani is putting his personal distaste for Trump aside and betting it’s best for New York City to keep things cordial so as to avoid drawing the president’s ire.

But as resistance to Trump remains animating for Democrats nationally ahead of November’s midterms, Mamdani’s strategy for engaging with him stands out.

Earlier today, Gov. Kathy Hochul made clear that she, for one, has no plans to meet with Trump while he’s in New York. “I speak to him on the phone whenever I need to,” she told reporters in Manhattan.

Hochul, who’s facing reelection in November and tends to directly criticize Trump more frequently than Mamdani, said it was her understanding that the mayor agreed to host the president at Gracie Mansion during a previous conversation at the White House.

“The mayor and [Trump] said that when he’s back in town again, he would go to Gracie Mansion,” the governor said. “I don’t have a Gracie Mansion to invite him to.”

Still, Hochul said there’s an opportunity for Mamdani to use the Gracie confab to push Trump on releasing federal funding for New York, including for law enforcement, that she said the president’s administration has been withholding.

“We have to continue fighting for what New York needs,” she said.

Mamdani’s office wouldn’t say who requested today’s meeting or share specifics about the expected focus in advance, only saying the mayor will talk to Trump about “issues affecting New York City.” A Mamdani spokesperson said the mayor will elaborate on what was discussed at a post-meeting press conference that Trump isn’t expected to attend.

After the appointment at Gracie, Trump is slated to meet with French President Emmanuel Macron before headlining a couple Republican fundraisers. By contrast, after his Trump tête-à-tête, Mamdani will have dinner with Vermont Sen. Bernie Sanders, who’s in the city to headline a United Nations Charter event this evening that will also feature pro-Palestinian activist Mahmoud Khalil, a person familiar with the plans who was granted anonymity to discuss them told Playbook.

See also  Christie: Trump Canceled Election Fraud Press Conference Because 'He's Scared' Of Jail

The Queens-born Trump is in town ahead of his Tuesday address to the United Nations General Assembly.

Maintaining a relationship with Trump isn’t without risk for Mamdani.

As Trump remains deeply unpopular amid the war in Iran and other controversies, some Democrats are privately questioning why the mayor sees a need to keep interacting with the president. But so far, Mamdani hasn’t faced any significant pushback from his hard-left base over his engagements with Trump, with leaders of the local chapter of the Democratic Socialists of America largely viewing it as the mayor acting in the city’s best interests. — Chris Sommerfeldt and Madison Fernandez 

From the Capitol

Governor Kathy Hochul spoke about New York's AI safety laws at a Monday event in Manhattan.

EYES ON AI: Hochul floated requiring safeguards like an artificial intelligence “kill switch” as part of state-level interventions to address the rapidly evolving technology.

During a Monday event in Manhattan rolling out next steps for enacting the RAISE Act, New York’s landmark AI safety law that is set to go into effect in January, the governor said she’ll “look closely at additional ways to build on” the legislation — including AI kill switches “if they’re deemed feasible and in the best interest of our state.”

The governor in recent days has vowed to take additional AI-related actions beyond the RAISE Act, but has not specified what that might look like. Her suggestion of a kill switch comes days after California Gov. Gavin Newsom issued an executive order to explore such a requirement for AI companies’ most-advanced models.

Some in the tech industry have argued implementing one is not technically feasible. Federal legislation to enact a kill switch requirement is currently stalled in Congress.

When asked to expand on the prospect of requiring a kill switch, Hochul said that “all options are on the table,” but wasn’t making a commitment.

“We’re going to do the research and make the decisions that are thoughtful to protect New Yorkers,” she said. “We’ll go as far as we need to to protect people of this state and ultimately this country in the absence of other leadership.”

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Read more from Madison Fernandez in POLITICO Pro.

MORE BLAKEMAN MONEY: Billionaire former casino developer Steve Wynn has donated $1 million to the main super PAC supporting Republican Bruce Blakeman’s gubernatorial bid, records filed with the state Board of Elections this morning show.

The committee, Strong and Safe New York, has now raised $5.3 million since July.

Wynn has been a top donor to national Republican causes for over a decade. His most recent large donations in New York came last year, when he gave $361,000 to the state GOP and $500,000 to a super PAC boosting Andrew Cuomo’s mayoral bid. — Bill Mahoney

FROM THE CAMPAIGN TRAIL

GOP Rep. Mike Lawler picked up an endorsement from his Democratic House colleague, Rep. Jared Golden of Maine.

ENDORSEMENT CORNER: Rep. Jared Golden (D-Maine) endorsed GOP Rep. Mike Lawler in his reelection campaign in suburban New York, Golden wrote in an opinion article published Monday.

Lawler is facing a tough reelection campaign against Democrat Cait Conley in one of the biggest House battlegrounds this November. The lawmakers have previously collaborated to advance the Northeast Lobsterman Protection Act, and are both members of the centrist Problem Solvers Caucus.

Golden, who is not running for reelection, was one of two House Democrats to break with the party and twice vote in favor of the Republican legislative agenda earlier in September.

“Mike Lawler has been a true partner to me and a friend to fishing families he will never represent,” Golden wrote. “I strongly back him, and I hope voters send him back to work. Wherever you live, find the members who pass laws with the other party, and keep them.”

House Minority Leader Hakeem Jeffries called the cross-aisle endorsement a “smoke and mirrors ploy” that “will do nothing to change the outcome of the race.”

“In desperation, [Lawler] is peddling an 11th hour endorsement from a retiring Congressmember who represents an out of town district more than 400 miles away,” Jeffries said in a statement. “Mike Lawler is an unadulterated phony who has never shown bipartisan courage when it matters.”

See also  Lin Wood Has Been Subpoenaed To Potentially Testify Against Trump

Read more from POLITICO’s Elleiana Green.

ON THE AIRWAVES: With fewer than 50 days to go before Election Day, House Democrats’ main super PAC is making its first TV ad buy in support of Conley on Monday.

The House Majority PAC said it is reserving $1.2 million on cable in the Hudson Valley contest. (An additional $1.2 million is going toward fighting Republican Rep. Tom Kean Jr.’s re-election in New Jersey, which is also covered by the New York City media market.) HMP said earlier this year that it didn’t include the high-dollar NYC media market in its initial reservations because it was “prioritiz[ing] markets where rates increase significantly.”

Republicans have been largely outpacing Democrats in NY-17 on the ad spending front, thanks to significant buys from super PACs backed by the president and House leadership. From the beginning of September through Election Day, the GOP has placed $15 million on ads across broadcast, cable, CTV and digital platforms, according to ad tracker AdImpact.

The new HMP spend is the biggest from an outside Democratic group so far, but still leaves a large gap between the parties. Democrats have placed around $3 million on advertising in the period between September and Election Day, with the largest chunk coming from the Conley campaign. — Madison Fernandez

IN OTHER NEWS

IN OTHER NEWS:

— JUDGES CASH IN: Brooklyn Democratic Party leaders have raked in $190,000 in contributions from judges and judicial candidates since 2012, raising some ethical and legal concerns. (New York Post)

— AFFORDABILITY AHEAD: Anthony Shorris, the mayor’s new pick for the president of the New York City Economic Development Corporation, laid out a vision for solving the city’s affordability crisis that goes beyond Mamdani’s vision for five city-owned grocery stores. (The New York Times)

— BUY NOW, PAY LATER: The Mamdani administration is pushing Albany for tougher ‘buy now, pay later’ regulation, as many New Yorkers use the plans to pay for basic essentials, sinking deeper into debt. (amNY)

Missed this morning’s New York Playbook? We forgive you. Read it here.

Art Dealing Trump
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