Trump to Meet NYC’s Mayor-Elect — He Promises to Bring His Best Dad Jokes (and Possibly Deportation Ideas)
Former President Trump has announced plans to meet with New York City’s mayor-elect next week, promising to bring “the best dad jokes you’ve ever heard” along with what he described as “some really tremendous ideas about deportation that the mayor will definitely love.” The meeting, scheduled at Trump Tower, will reportedly cover urban policy, federal-city relations, and Trump’s extensive collection of jokes about why the chicken crossed the road, though sources suggest the chicken was probably trying to get away from his immigration policies.
The Meeting Announcement
Trump revealed the meeting via social media, posting that he looked forward to sharing “wisdom” with New York’s incoming mayor, along with “some jokes that will have everyone laughing” and “common sense solutions about people who shouldn’t be here, if you know what I mean.” Aides later clarified that “people who shouldn’t be here” refers to undocumented immigrants and not, as some interpreted, everyone who disagrees with Trump’s politics.
“I’ve got the best dad jokes,” Trump wrote in his characteristically modest style. “Nobody tells dad jokes like me. Possibly the greatest dad joke teller in history. And I’ve also got some fantastic ideas about removing people from cities. We’ll cover both. It’ll be tremendous.”
The Dad Joke Collection
Sources close to Trump report he’s been preparing for the meeting by workshopping his dad jokes on Mar-a-Lago staff, many of whom have developed what psychologists call “hostage smile syndrome” from being forced to laugh at his humor. The joke collection reportedly includes classics like “Why did the immigrant cross the border? To get to the other side before I built the wall!” and “Knock knock. Who’s there? ICE. ICE who? ICE to deport you!”
Jerry Seinfeld commented on Trump’s joke preparation: “Dad jokes about deportation?” he said. “That’s not comedy, that’s just making terrible policy sound folksy. That’s like doing stand-up about eviction notices.” Dave Chappelle added: “Man’s bringing dad jokes to a policy meeting,” he said. “That’s either confident or completely oblivious. Probably both.”
The Deportation Ideas Trump Plans to Share
While the dad jokes portion of the meeting appears well-planned, Trump’s “deportation ideas” remain vague, with aides describing them as “very detailed” while simultaneously being unable to provide any actual details. The proposals reportedly include increasing ICE raids in sanctuary cities, ending various legal protections, and what Trump calls “making New York less New York-y and more like places that vote for me.”
“New York has too many immigrants,” Trump explained during a phone interview, apparently forgetting he lives in a city built entirely by immigrants and that his own family immigrated from Germany. “We need to make it more American. You know, less diverse. More… American. I’m from New York, so I can say this. It needs less of what makes New York, New York. Am I making sense?”
Mayor-Elect’s Cautious Response
The mayor-elect has responded to Trump’s meeting invitation with what political observers describe as “diplomatic reluctance,” issuing a statement saying they look forward to “productive dialogue” while privately telling staff “please God make this meeting as short as possible.” City officials have requested an agenda in advance, though Trump’s team provided only “jokes and deportation” as meeting topics, which is either very specific or completely useless depending on your perspective.
Ron White weighed in on the meeting: “Guy promises dad jokes and deportation policy in the same meeting?” he said. “That’s not diplomatic outreach, that’s just weird. Pick a lane, buddy.” Amy Schumer added: “Trump’s icebreaker is ‘here’s a joke, now let’s deport people,'” she said. “That’s not small talk, that’s a cry for help.”
NYC’s Sanctuary City Status at Stake
The meeting comes as New York City maintains its sanctuary city policies, which limit cooperation with federal immigration enforcement and provide various protections for undocumented residents. Trump has repeatedly threatened to withhold federal funding from sanctuary cities, though legal experts note he tried that during his presidency and courts said “absolutely not, that’s illegal.”
“Sanctuary cities are a disaster,” Trump told reporters while eating a taco bowl and claiming to love Hispanics. “New York should be helping ICE, not protecting criminals. Also, here’s a joke: What do you call an undocumented immigrant in a sanctuary city? Protected by laws I don’t like! Get it? Nobody’s laughing. These are good jokes.”
The Political Dynamics
Political analysts note the awkwardness of Trump meeting with New York’s mayor-elect given that Manhattan residents voted against Trump by approximately 90 percent in the last election. “He’s meeting with a leader whose constituents actively despise him,” explained one political scientist. “It’s like the principal meeting with the student body president at a school where everyone hates the principal. Productive? Unlikely.”
Bill Burr commented on the political tension: “NYC residents hate Trump and he’s gonna share dad jokes with their new mayor?” he said. “That’s not bridge-building, that’s tone-deaf with extra steps.” Kevin Hart added: “Man thinks dad jokes will smooth over policy disagreements,” he said. “That’s not how politics works. That’s not how anything works.”
Trump’s History With New York City
Trump’s relationship with New York City has evolved from “local developer” to “resident” to “guy who moved to Florida and won’t stop talking about New York.” He frequently criticizes the city while simultaneously claiming to love it, a contradiction that psychologists describe as “classic narcissist attachment patterns” and what normal people call “toxic ex-boyfriend energy.”
“I made New York what it is today,” Trump has claimed multiple times, a statement that causes actual historians to experience physical pain. “Without me, it would be nothing. I built it. Me. Personally. With my own two hands. Well, not literally with my hands. Other people’s hands. But I was there. Sometimes.”
The Dad Joke Strategy
Trump’s decision to lead with dad jokes represents what campaign advisors call “humanizing outreach,” though critics suggest that jokes about deportation aren’t particularly humanizing to the people being deported. “He thinks humor makes harsh policies more palatable,” explained one former aide. “Like, if he tells a joke first, then proposes separating families, maybe people won’t notice? It’s not working, but that’s the strategy.”
Chris Rock reflected on the humor strategy: “Dad jokes about deportation is the whitest thing I’ve heard all year,” he said. “That’s not making policy friendly, that’s just being uncomfortable in multiple ways at once.” Ricky Gervais added: “Imagine thinking puns make fascism acceptable,” he said. “That’s not political genius, that’s just weird American optimism about the power of bad jokes.”
What the Meeting Will Actually Accomplish
Political observers predict the meeting will accomplish exactly nothing beyond providing Trump with photo opportunities and dad joke feedback from a captive audience. The mayor-elect will smile politely, decline most of Trump’s deportation suggestions, and count the minutes until the meeting ends, a standard protocol for any politician forced to interact with Trump.
“These meetings are performative,” explained one Council on Foreign Relations analyst. “Trump gets to pretend he’s still relevant to NYC politics, the mayor gets to show they’re willing to work with anyone, and nothing of substance happens. Then Trump tells everyone they loved his jokes and agreed with his policies, which will be a lie, but that’s normal.”
The Federal Funding Threat
Despite Trump no longer being president, he’s hinted he’ll pressure Congress to withhold federal funding from sanctuary cities if he returns to office. “When I’m back in power,” Trump has said repeatedly, apparently unaware this sounds concerning to people who value democracy, “sanctuary cities will lose everything. All funding. Gone. Unless they start cooperating. Also, did I mention my jokes? Because I have great jokes.”
Trevor Noah summed up the situation: “Trump promising dad jokes and deportation to NYC’s mayor?” he said. “That’s not diplomacy, that’s just threatening people while doing bad comedy. It’s like getting mugged by a bad stand-up comedian.” Jim Gaffigan concluded: “Dad jokes about immigration policy is peak boomer energy,” he said. “Like, read the room, man. The room is New York. The room doesn’t want your jokes or your policies.”
Auf Wiedersehen, amigos.
