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Questions Arise About Jack Schlossberg’s Readiness for Congress

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Questions Arise About Jack Schlossberg’s Readiness for Congress

Good morning. It’s Friday. We’ll look at the Manhattan congressional campaign of Jack Schlossberg, President John F. Kennedy’s grandson. We’ll also get details on an obscure metric that will figure in the new second-home tax in New York City.

Jack Schlossberg is one of nine candidates running for a House seat in Manhattan. When he entered the race, he was known for his social media personality — and for being President John F. Kennedy’s grandson. But rapid staff turnover and Schlossberg’s own erratic actions have gotten attention in the New York political world. With the Democratic primary only six weeks away, I asked my colleague Nicholas Fandos for an assessment.

His campaign sounds like it’s not ready for prime time. Is that a reasonable assessment? This is the first time he’s run for office.

There are few political campaigns that I’ve covered that are not at least a little messy. It comes with the territory. But the degree of the messiness in Schlossberg’s campaign, and the specifics, are unusual.

He has had a surprisingly high rate of staff turnover — at least two campaign managers, two field directors, a handful of advisers and a rotating cast of consultants in the six months since he announced his candidacy.

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On the day of his campaign launch, Schlossberg said he needed to nap and then was unreachable for most of the rest of the day, which left his team scrambling. A couple of weeks after the announcement, he had a run-in with a sitting congressman who felt that Schlossberg had ripped off his social media commentary.

Many candidates run on their records. What does Schlossberg list as accomplishments when he’s asked?

Schlossberg has relatively little professional experience, so when he talks about what qualifies him for the job, he brings up things like receiving law and business degrees at Harvard, scoring near the top on the bar exam and being an E.M.T. in college. He’s also worked as a freelancer for Vogue and as an assistant at the State Department, but both of those gigs lasted only a few months. And he readily points out that he has built a large social media following.

There is no standard set of qualifications to be a member of Congress, but most people who run have worked their way up through local government or careers in business or the law. Sclossberg has not followed any of those paths.

What was that social media dust-up about?

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Social media seems to be one of Schlossberg’s biggest strengths, but it’s also potentially a vulnerability. He has built a large audience with revealing, funny and sometimes outright bizarre posts that are captivating to some and alienating to others.

I found that in at least one case in this campaign, he essentially mimicked a video from Representative Seth Moulton, a Democrat from Massachusetts, commenting on President Trump’s policy on Venezuela. He made his own video, saying almost the same thing Moulton had said. He rewrote the words, but it was still very close.

Moulton’s team was so taken aback that they reached out to Schlossberg, asking, What gives? They were told that he had indeed copied Moulton’s post because he had liked it so much. This may be common social media practice, but it’s traditionally been a no-no in politics.

What about fund-raising? Has he raised more than his opponents?

He’s doing well on fund-raising. He’s not at the front of the pack, but he has raised $2.3 million from donors.

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Some of that has come from small donations across the country, and others from large checks from friends of his famous family. He has his own substantial wealth but has said that he does not intend to spend any of it on the race.

Is he the front-runner right now?

There has not been good polling. The internal polls that we have seen show that he’s a slight favorite in a crowded field that includes two state assemblymen, Micah Lasher and Alex Bores. Lasher is a protégé of Representative Jerrold Nadler, who’s vacating the seat they’re all running for.

Two of the other candidates are George Conway, a former Republican who has become one of President Trump’s biggest critics, and Nina Schwalbe, a global health expert.

Schlossberg did not talk to you when you were reporting the story you wrote. What did his aides tell you about Schlossberg’s management of his campaign and the turnover of his staff?

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Schlossberg’s campaign did not dispute most of the details in my story. They downplayed the significance of the staff turnover, saying no one should be surprised that a first-time candidate, especially one as intense as he is, would cycle through staff members in a high-pressure campaign.

In addressing his occasional absences from the campaign, they pointed out that the campaign had coincided with the death of his sister Tatiana Schlossberg, from cancer.


Weather

Sunny skies with a high around 67 degrees. Tonight will be mostly clear with a low near 54.

ALTERNATE-SIDE PARKING

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In effect until May 22 (Shavuot).

QUOTE OF THE DAY

“I’m standing behind a mylar curtain, building the character. I part the curtain, stand in a fixed position, and allow the audience to feed me with shouts of joy and respect and admiration and whatever else they’re thinking. Let the people have what they came for. Apotheosis.” — André De Shields, who plays the godlike Old Deuteronomy in “Cats: The Jellicle Ball,” on how he gets into character.


What’s the “market value” of your co-op or condo?

Those two words are in quotation marks for a reason. In New York City, the “market value” of an apartment may not be what it sells for, because “market value” is a bureaucratic metric that often underestimates an apartment’s actual worth.

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“Market value” will figure in the new tax surcharge on part-time residents of the city. As proposed by Gov. Kathy Hochul, the second-home tax plan would initially target co-ops and condos that have a “market value” of at least $1 million. They would be taxed an extra 4 percent to 6.5 percent in addition to their existing property taxes.

How many apartments would be affected is unclear. The governor’s office says that an apartment with a “market value” of $1 million would sell for about $5 million. But the disparity is often more pronounced: One Midtown Manhattan penthouse with a “market value” of about $4.2 million sold for more than $135 million last year.

The surcharge has been the talk of the New York political world since Hochul announced it last month. It wouldn’t bring in as much revenue as some of its boosters had wanted, but Mayor Zohran Mamdani cast it as an example of how government was making good on his promise to tax the rich.

The “market value” metric would govern second-home surcharge payments for only the first two years of the new tax. After that, the city and the state would rely on a different measurement to determine which properties are above the threshold. That new metric would be added to a tax system that many taxpayers already find impenetrable.

“I know we just sent people around the moon and back, so you’d think anything is possible,” said Jason Haber, a real estate broker and a co-founder of the American Real Estate Association. “But because of how the city tax system is set up, this is crazy complicated in the first place. And they tried to rush it though, I think without fully appreciating its complexity.”

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METROPOLITAN diary

Dear Diary:

It was a Saturday, and I was on Fifth Avenue and 14th Street. Two young women were walking and talking behind me.

“Is there anything you need at the market?” one said.

“The will to live,” the other replied.

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I couldn’t help myself.

“I don’t think they sell that there,” I said.

We all laughed and kept going.

— Nancy Lane

Illustrated by Agnes Lee. Tell us your New York story here and read more Metropolitan Diary here.

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New York

How Tony Danza Spends a Day Playing a Villain and Frank Sinatra

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How Tony Danza Spends a Day Playing a Villain and Frank Sinatra

Tony Danza is making up for lost time.

“One of the things I most regret about my life is that I didn’t take advantage of my youth,” said Mr. Danza, 75. “I had a great time, but nobody handed me an instrument and said, ‘Try this.’”

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Now he is learning how to speak Spanish, play the piano and a cornet.

Mr. Danza, best known for his leading roles in the television series “Who’s the Boss?” and “Taxi,” has been entertainment’s jack-of-all-trades for decades. Yet he’s still striving to be the best singer, dancer and actor he can be.

“What I am is a guy with finite time who wants to get in as much as he can while he can,” he said.

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Mr. Danza spent a Friday with The New York Times as he got ready for two performances, including a one-man show at Café Carlyle.

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Video: Protesters Clash with Federal Agents Outside ICE Detention Center in New Jersey

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Video: Protesters Clash with Federal Agents Outside ICE Detention Center in New Jersey

new video loaded: Protesters Clash with Federal Agents Outside ICE Detention Center in New Jersey

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Protesters Clash with Federal Agents Outside ICE Detention Center in New Jersey

Protesters and immigration agents clashed outside Delaney Hall detention center in Newark, where activists have gathered for days to denounce conditions inside.

“Get back!” “Get back, get back, get back, get back, get back!” [chanting] “ICE, ICE has got to go. Hey, hey, ho, ho.” “We’ve heard repeatedly about these horror stories of pregnant women not getting access to care, of people with injuries not being treated. People shouldn’t have to starve themselves to make their dignity known.” “Down, down with the degradation.” “Down, down with the degradation.”

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Protesters and immigration agents clashed outside Delaney Hall detention center in Newark, where activists have gathered for days to denounce conditions inside.

By Christina Kelso

May 28, 2026

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New York

How a Family of 4 Lives on $225,000 a Year in Washington Heights

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How a Family of 4 Lives on 5,000 a Year in Washington Heights

How can people possibly afford to live in one of the most expensive cities on the planet? It’s a question New Yorkers hear a lot, often delivered with a mix of awe, pity and confusion.

We surveyed hundreds of New Yorkers about how they spend, splurge and save. We found that many people — rich, poor or somewhere in between — live life as a series of small calculations that add up to one big question: What makes living in New York worth it?

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Ellen Hagan grew up in a small town in Kentucky, and moved to New York City as quickly as she could after she graduated from college. She arrived a few weeks before Sept. 11, and tried to get her bearings in a city turned upside down.

She found a group of fellow young artists and writers who wanted to take advantage of everything they could in the city, on very limited budgets. They went to poetry readings and dance parties, and rented tiny apartments in the East Village.

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All the while, Ms. Hagan was diligent about saving money, even when she had very little of it.

“I didn’t know what I was saving for, but I knew I wasn’t going to have a job that would give me a pension,” she said. “I wanted to make enough money to live the New York existence I was dreaming of.”

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Ellen Hagan learned to be diligent about saving money after she moved to New York.

Twenty-five years later, Ms. Hagan and her husband, David Flores, whom she started dating in her early years in New York, have much more money than they used to. Still, they feel more anxious about money than they hoped they would at this point in their lives.

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The couple both work at DreamYard, a Bronx arts nonprofit. Last year, they made $178,135 there collectively, with Ms. Hagan, 47, directing the poetry and theater programs, and Mr. Flores, also 47, serving as the head of visual art and design.

They typically bring in another $40,000 to $60,000 a year through their freelance work. Mr. Flores is an adjunct professor, a photographer and a filmmaker, and Ms. Hagan teaches at a graduate writing program and writes books and poetry. They try to set aside about 15 percent of their income each year to grow their savings.

The couple live in Washington Heights in Upper Manhattan with their two daughters, who are 12 and 15.

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Homeownership Doesn’t Solve Everything

As a young couple, Ms. Hagan and Mr. Flores lived in a 400-square-foot East Village rental. When their rent started to tick up, Ms. Hagan began looking for a place to buy, seeing homeownership as a buoy that would all but guarantee a secure financial life in New York.

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Sixteen years ago, the couple found a perfect apartment in Washington Heights and scrambled to cobble together a down payment. They pooled their savings to put a 15 percent down payment on the $335,000 home. Once they closed, they were left with only a few hundred dollars in savings, but were thrilled and relieved.

“I had this sense that when you buy, you’re set in New York City,” Ms. Hagan said.

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The reality, she has found, is more complicated.

The couple’s mortgage payment is $1,300 a month, and their maintenance fees keep rising, partially as a result of a new local law that requires increased inspections and repairs for buildings. Local Law 11 boosted their maintenance by $462 a month, at least temporarily, to about $1,900 total. And when the building’s management installed a new security system, each unit had to chip in $95 a month for three months.

Ms. Hagan loves the apartment, but she worries that they may eventually be priced out of their neighborhood.

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“This building isn’t going to be for us at some point,” she said. “This feels like, uh oh, they’re imagining people who have much higher incomes than we do.”

Keeping the Kids Busy

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Ms. Hagan and Mr. Flores, who each maintain packed calendars, have encouraged their daughters to adopt the same approach to city living.

“I’m definitely a proponent of, let’s fill your schedule and see what you love,” Ms. Hagan said.

The girls’ public school offers free debate and band classes before and after school, and they’ll appear this spring in the school’s productions of “Annie” and “The Addams Family.”

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The girls are also enrolled in a free theater academy at the People’s Theatre and writing workshops at Uptown Stories, which has a pay-what-you-can system. Ms. Hagan and Mr. Flores typically pay the full tuition, which is $800 for each 12-week session, and donate about $2,500 a year to the organizations their daughters are part of.

The couple’s older daughter, Araceli, who wants to be both a writer and a doctor, is enrolled in a medical training program for middle and high school students. She made $2,500 for completing an internship at a cardiothoracic intensive care unit last summer.

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Their younger daughter, Miriam, is going to a Y.M.C.A. camp this summer, which costs $2,600 for two weeks.

Ms. Hagan and Mr. Flores spent about $500 total on holiday gifts for both girls, and the couple doles out their daughters’ weekly allowances in two installments: $25 on Mondays and $25 on Fridays.

They shook their heads when Miriam, who is known as the most stylish member of the family, came home one day wearing a Dr Pepper T-shirt she’d bought at Target.

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“We were like, ‘What are you doing with your money?’” Ms. Hagan said.

The Fun Stuff

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The extra income from the couple’s freelance work allows the family to splurge on theater, vacations, books and memberships at the Museum of Modern Art and the Whitney Museum of American Art.

Sometimes, Ms. Hagan and Mr. Flores work together. A few years ago, they sold a young adult novel called “Tell Me Every Lie” they had co-written for a $35,000 advance, some of which went to their agent.

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Every little bit helps. The family is spending a weekend on Long Beach Island in New Jersey this summer, which will cost about $3,500. That price tag includes a hotel room big enough for four.

The family typically travels twice a year to Kentucky, where both Ms. Hagan and Mr. Flores are from, and where the couple co-owns a home in Louisville with Mr. Flores’s parents. They put $40,000 down and spend about $12,000 annually on expenses related to the home.

The family was hoping to travel to the Philippines this year, where Mr. Flores’s father is from, but they realized it could cost as much as $15,000. The trip is now on hold indefinitely.

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They spend about $700 a month on groceries from nearby supermarkets, and occasionally order grocery deliveries from FreshDirect.

Every Wednesday, when the girls come home late from theater class, someone picks up dinner at the nearby halal truck or the Dominican restaurant Malecon, which usually runs about $60.

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Dinner out as a family of four can easily cost $200, so Ms. Hagan and Mr. Flores typically eat at restaurants just once or twice a month. The other night, the whole family was hungry and craved Italian food from a favorite upscale spot nearby.

They balked, and walked around the corner to a diner instead. The meal was $120, all in.

We are talking to New Yorkers about how they spend, splurge and save.

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