Every year, the New York City philanthropy Robin Hood tries to outdo itself with a party so good that New York’s rich and famous will be moved to open their wallets and collectively give tens of millions of dollars to combat poverty in the city.

The charity pulled in nearly $69 million last year at its annual gala, which is billed as one of the largest one-night fund-raisers on the planet.

This year, the stakes were dramatically higher.

Enormous federal budget cuts to social service programs threatened to plunge hundreds of thousands of New Yorkers into poverty, and Robin Hood’s leaders hoped to persuade partygoers to dig deeper than ever in response to the emergency.

At the same time, they knew they had to avoid making an overtly political pitch — blaming President Trump or the Republicans in Congress — or risk alienating their conservative donors and wealthiest benefactors, virtually all of whom would benefit from the tax cuts that were also included in the president’s signature budget-cutting bill.

It was a high-wire act that has eluded many other institutions in the Trump era. For Robin Hood, according to interviews with 20 board members and supporters, grantees and staff members, the moment was a critical test in a moment of entrenched polarization.

For New York City, which has benefited from nearly $3 billion in charitable donations from Robin Hood over the past 40 years, the organization’s success was crucial.

On the night of the gala, on a Monday evening in May, Robin Hood wooed 3,500 guests to the Javits Center in Manhattan. Attendees were served cocktails under an enormous basketball hoop lit up in neon and watched boxers swing at punching bags stamped with the hashtag #fightpoverty.

Keith Urban and the Weeknd performed. Seth MacFarlane did a stand-up set, ribbing the various billionaires and multimillionaires in the room.

The leaders of nonprofit groups who depend on Robin Hood funding appeared on video, describing doomsday scenarios.

Already, they said, immigrants were no longer dropping their children off at prekindergarten for fear of being caught up in a raid. Cuts to food stamps could create an entire city’s worth of newly hungry people. The leaders warned that New York — a city where Robin Hood-funded research had found that one in four people were now living in poverty — was poised to become a diminished version of itself.

“In the more than two decades that I have served on the board of Robin Hood, I have never seen a more severe crisis facing the most vulnerable New Yorkers,” said Geoffrey Canada, the president of Harlem Children’s Zone, an anti-poverty group.

The billionaire hedge fund manager Paul Tudor Jones, who co-founded Robin Hood in the late 1980s and helped burnish the charity’s reputation as Wall Street’s solution to income inequality, was the evening’s closer.

He was dressed as Carnac the Magnificent, a fictional soothsayer played decades ago by Johnny Carson on his late-night show. “You don’t have to be in the prediction business to see what’s coming,” he said, warning of a “great poverty crisis” on the horizon.

“The U.S. government has told us they are getting out of the business of taking care of the poor,” he said.

“I’m not saying what’s right or wrong,” Mr. Tudor Jones added. “I’m just saying what’s true.”

The Coming Storm

Robin Hood needed to sound the alarm for its donors, but the charity’s leaders had already spent months worrying about potential cuts to food assistance and Medicaid.

That concern was cemented on a winter morning soon after Mr. Trump’s second inauguration.

A line of black cars pulled up to a charter school in the South Bronx and deposited some of America’s most powerful people on the curb outside.

They assembled in a room with soaring ceilings befitting the former ice factory that was now the newest outpost of the Dream charter school network, a Robin Hood grantee. Other members of the charity’s board and leadership council called in from afar.

The group included Dina Powell McCormick, the former deputy national security adviser during Mr. Trump’s first term, an assortment of hedge fund titans, including Glenn Dubin of Dubin & Co. and David Einhorn of Greenlight Capital, and Alexis Ohanian, a co-founder of Reddit.

Richard R. Buery Jr., Robin Hood’s chief executive, a former nonprofit leader who helped create New York’s universal prekindergarten program, kicked things off.

The mood was urgent, almost frantic, according to conversations with eight attendees.

Technology entrepreneurs, academics and television news anchors traded notes and rumors about which social service programs were likely to be on the chopping block under the new administration.

“Everyone was just trying to get their bearings,” said DeRay Mckesson, a criminal justice activist who helped found Black Lives Matter and sits on Robin Hood’s leadership council. “We were just trying to catalog the cuts.”

Some members wondered whether the most politically connected among them should make calls to Washington to try to blunt the cuts.

There were options, and powerful people the board could call on.

Ms. Powell McCormick, a former Robin Hood board chair who remains on the group’s executive committee, is married to David McCormick, a Republican senator from Pennsylvania.

Scott Bessent, Mr. Trump’s treasury secretary, participated in a Robin Hood fund-raiser a few months before he joined the administration, when he was still running a hedge fund.

The hedge fund billionaire Bill Ackman, who supported Mr. Trump’s 2024 campaign, won Robin Hood’s stock-picking bracket this year, a fund-raiser that brought in over $400,000.

The group debated the potential drawbacks of pursuing a more political strategy.

In interviews, some of Robin Hood’s most influential supporters and benefactors argued that the charity had built its reputation on maintaining a big tent of nonprofits, wealthy captains of industry and elected officials, all focused on what had long been a consensus goal of helping New York’s most vulnerable. That work could be unraveled, they warned, if Robin Hood were perceived as being part of the anti-Trump resistance.

Others, including some nonprofit leaders, said there was no better time for Robin Hood to tap into its well-connected donor base, to try to persuade politicians in Washington to preserve the social safety net.

Still others argued that many of the problems facing New York City, chiefly the influx of migrants, had been overseen by Democratic leaders.

The Night’s Haul

Robin Hood’s board ultimately decided that the charity should be singularly focused on raising money, to try to top the $130 million it had given away the year before, and keep its distance from political activity.

The charity recently announced that it had given away $49 million in the first half of the year alone, and said it was making plans to fund its first endowment, aiming to raise $1 billion over the next decade.

At the gala in May, the grand finale came when the night’s final haul was announced, lighting up screens across the room.

The number was huge by any objective measure: nearly $72 million.

But it was about the same as the amounts raised in recent years. And it did not come close to the total in 2015 — $101 million, among the highest figures ever raised at the gala — when Mr. Ackman threw in $25 million.

By July, when Mr. Trump’s legislation passed Congress, it became clear how much more was needed to even begin to plug the holes left by the government.

About 1.5 million New Yorkers could lose access to Medicaid, and 300,000 could lose their food-stamp benefits.

“A thousand Robin Hoods couldn’t replace Medicaid,” Mr. Buery, the charity’s chief executive, said in an interview.

Still, he added, “we can do as much as humanly possible, and we can ask New Yorkers who care to do as much as humanly possible, so that struggling New Yorkers and the institutions that serve them can survive this moment.”

Kirsten Noyes contributed research.