A federal judge overseeing New York City’s jails took Rikers Island out of the city’s control on Tuesday, ordering that an outside official be appointed to make major decisions regarding the troubled and violent jail complex.

The judge, Laura Taylor Swain, said in a 77-page ruling that the official would report directly to her and would not be a city employee, turning aside Mayor Eric Adams’s efforts to maintain control of the lockups. The official, called a remediation manager, would work with the New York City correction commissioner, but be “empowered to take all actions necessary” to turn around the city’s jails, she wrote.

“While the necessary changes will take some time, the court expects to see continual progress toward these goals,” Judge Swain wrote.

The order comes nearly a decade after the city’s jails, which include the Rikers Island complex, fell under federal oversight in the settlement of a class-action lawsuit. The agreement focused on curbing the use of force and violence toward both detainees and correction officers. A court-appointed monitor issued regular reports on the persistent mayhem.

New York City has held onto its control of Rikers with white knuckles — struggling to show progress and reaching the brink of losing oversight of the jails as critics of the system have called for a receiver. Conditions have not improved, according to lawyers for the plaintiffs and the federal monitor.

The city’s jail population has grown to more than 7,000 from a low of about 4,000 in 2020. And in the first three months of this year, five people died at Rikers or shortly after being released from city custody, equaling the number of detainees who died in all of 2024.

In a statement, lawyers from the Legal Aid Society and Emery Celli Brinckerhoff Abady Ward & Maazel, which represent detainees, said they commended the court’s “historic decision.”

“For years, the New York City Department of Correction has failed to follow federal court orders to enact meaningful reforms, allowing violence, disorder and systemic dysfunction to persist,” said Mary Lynne Werlwas and Debra Greenberger. “This appointment marks a critical turning point.”

The remediation manager will be a receiver in all but name. The official will be granted “broad powers” as plaintiffs had asked, Judge Swain wrote, but will also develop a plan for improvement in concert with the correction commissioner.

Such arrangements are the last resort for a troubled jail or prison. Since 1974, federal courts have put only nine jail systems in receivership, not counting Tuesday’s Rikers order.

The ruling was another blow for Mr. Adams, who is fighting for his political life after the Trump administration dropped corruption charges against him so that he could assist with its deportation efforts. Many of his confidants have also faced investigations, he is on his fourth police commissioner and his approval ratings have hit historic lows.

Now, the mayor, a former police captain, has lost most control of an institution that employs about 5,000 people represented by the Correction Officers’ Benevolent Association, a union that has been a bastion of political support.

On Tuesday, even as prisoners rights organizations and some of Mr. Adams’s campaign opponents celebrated, the mayor disputed whether Judge Swain’s order constituted a receivership and painted it as a benefit.

“The problems at Rikers are decades in the making,” he said. “We finally got stability.”

In a statement, Benny Boscio, president of the correction officers’ union, said that Judge Swain’s order had preserved the right to representation and collective bargaining, and he made clear that the guards must be reckoned with.

“The city’s jails cannot operate without us,” he said. “And no matter what the new management of our jails looks like, the path toward a safer jail system begins with supporting the essential men and women who help run the jails every day.”

New York City has spent more than $500,000 per inmate annually in recent years, according to city data, well beyond what other large cities have spent, and yet detainees still sometimes go without food or proper medical care.

A New York Times investigation in 2021 found that guards are often stationed in inefficient ways that fail to protect detainees. And although the jail system has consistently been the most well-staffed in the United States — there is roughly one uniformed officer for each inmate at Rikers, according to city data — an unlimited sick leave policy and other uses of leave have meant that there are too few guards present to keep inmates safe.

The class-action lawsuit that led to the takeover, known as Nunez v. City of New York, was settled in June 2015 and required that the jails be overseen by a court-appointed monitor who would issue regular reports on conditions there but would wield no direct power to effect change.

Through those reports, Judge Swain was given an extensive history of the cyclical nature of the jail system’s problems. Through the administration of two mayors and several correction commissioners, the jails continued to devolve, according to prisoners’ rights advocates and the monitor’s reports. In November, the judge found the city in contempt for failing to stem violence and excessive force at the facility, which is currently run by Correction Commissioner Lynelle Maginley-Liddie.

Over the years, the city has argued that the Department of Correction has made progress, even as Judge Swain issued remedial orders and the monitor and prisoners’ advocates pointed to backsliding.

In 2023, Damian Williams, then Manhattan’s top prosecutor, joined calls for the appointment of an outside authority to take control of Rikers, saying that the city had been “unable or unwilling” to make reforms under two mayors and four correction commissioners.

On Tuesday, Jay Clayton, whom President Trump appointed last month as interim U.S. attorney, said Judge Swain’s decision was a “welcomed and much needed milestone.”

In a 65-page opinion last year, Judge Swain said that the city and the Department of Correction had violated the constitutional rights of prisoners and staff members by exposing them to danger, and had intentionally ignored her orders for years. Officials had fallen into an “unfortunate cycle” in which initiatives were abandoned and then restarted under new administrations, she wrote.

An inability to operate independently of politics is what has kept Rikers from turning around, said Elizabeth Glazer, the founder of Vital City and a former criminal justice adviser under Mayor Bill de Blasio.

“Every new administration, there’s a reset,” she said. “Every new crisis, there’s a reset.”

Last year, Judge Swain ordered city leaders to meet with lawyers for prisoners to create a plan for an “outside person,” known as a receiver, who could run the system.

The parties met in recent months to try to reach an agreement, in deliberations overseen by the federal monitor, Steve J. Martin. He told the court that the parties and his team had been “actively engaged” in discussions.

In the end, the sides submitted dueling proposals.

The Legal Aid Society and a private law firm representing incarcerated people argued that the court should strip the city of control and install a receiver who would answer only to the court. The receiver should be given broad power to make changes, they proposed, including with regard to staffing and union contracts that govern it.

The receiver, they said, could “review, investigate and take disciplinary or other corrective or remedial actions with respect to violations of D.O.C. policies, procedures and protocols” related to the court order.

In its plan, the city offered to give Ms. Maginley-Liddie dual roles by adding the title of “compliance director” to her responsibilities. The city proposed that she answer to the court on issues related to the consent decree, such as safety and staffing shortages, while answering to the mayor on everything else.

However, the city has had a “a multitude of opportunities” to improve its management of the jails and has “proven unable or unwilling to take advantage of those opportunities,” said Hernandez D. Stroud, a senior fellow at the Brennan Center for Justice at the New York University School of Law.

“Judge Swain was left no other choice,” he said.

Emma G. Fitzsimmons contributed reporting.

Initiation

Dear Diary:

It was the early 2000s. I had been resisting my friends’ invitations to join them in a night of dancing at one of those only-in-New-York, late-night parties held in the kind of dark, crowded clubs that were tucked into quiet streets along the Hudson River at the time.

Intense, sweat-soaked group experiences like that didn’t appeal to me.

At some point, I gave in and spent six hours one night dancing as hard as I possibly could. It was magic. I had found my tribe.

As the early spring morning broke over Manhattan, seven of us left the club together, footsore, sweaty, exhilarated and exhausted, and then settled in for breakfast at a nearby diner.

I felt as if I had been initiated, let into the heavy rites of a secret fraternity. I was now one of those guys.

A world-wise waitress came to the table and scoped out the group.

“Oh, puppy!” she said. “Puppy! What happened to you? Did you get off the porch and play with the big dogs?”

I nodded.

“Don’t say a word,” she said. “I know just what you need.”

She took the other six orders and went to the kitchen. She returned a few minutes later, bringing me a mound of scrambled eggs, several strips of bacon, a toasted bagel and a big glass of cranberry juice.

It was best breakfast of my life.

— Gary Clinton

Tiramisu

Dear Diary:

He slid the oval dish toward us, a perfectly clean column of cream waiting at the edge of the plate, an arrow made of ladyfingers and mascarpone pointed directly at our hearts.

Befuddled, we looked at him, then at the bartender’s face, which evolved from confusion to adoration.

“Here,” said the stranger I had been shoulder to shoulder with as we ate an Italian supper on a Saturday night in Carroll Gardens. He gestured toward his plate of tiramisu (well, our plate of tiramisu). “You try it.”

Just a few minutes before, I had gestured toward the plate with my eyes while craving it under my breath to my friend.

The two of us had shared a regretful, longing glance: We should have gotten dessert. Now, we were being offered the last bite of someone else’s.

I was almost afraid to ask the bartender for a spoon. Was this kind of sharing allowed?

Before I could think too hard, shiny silver spoons were resting on the counter, then caressed in our hands, then sinking into the custard with an Olympic diver’s grace, and then, satisfyingly, into our open mouths.

It turned out the owner’s father came into the place every morning and made the tiramisu by hand.

— Jordana Hope Bornstein

Isn’t It Delicious?

Dear Diary:

Marilyn, you’re dead, but I am alive
Standing on a subway grate
Your subway grate
On the southwest corner
Of 52nd and Lexington
There are no signs of any sort
No indication of commemoration
Drip, Drip, Drip, raindrops
Zoom, Zoom, Hustle & Bustle
New York’s in motion
While I stand soaked, remembering
The poems you used to write
I loved the one about the bridges
I’ve read it at gigs
It always gets a big response
Marilyn, you’re dead, but I’m alive
Issuing a reminder
So you can remember
You are not going alone

— Danny Klecko

Sunshine Boy

Dear Diary:

It was spring 1975. I was 23 and had been in New York for less than six months. I was working as a secretary at Artkraft Strauss, and “The Sunshine Boys” was filming around the corner.

During one lunch hour, Walter Matthau appeared in a shabby overcoat. Gathering all of my courage, I asked him for an autograph.

Almost smiling, he asked my name.

I panicked. Should I ask for two autographs? Would that be too much? I decided not to risk it.

“Oh, it’s not for me,” I said. “It’s for my mother, Ruth.”

Giving his best scowl, he scribbled a line and stomped off.

My mother still had that autograph when she died 13 years ago. I have it now.

— Amanda Sherwin

Tumbling

Dear Diary:

My husband and I were in New York to see “Good Night and Good Luck,” and I had gotten done up for the occasion: dress, hair, makeup, jewelry, a stunning but impractical white coat and an infrequently worn pair of kitten heels.

As we walked to the theater, the promise of spring was in the air, and I was feeling upbeat. I was gliding along. The next thing I knew, I was tumbling in slow motion onto the dirty pavement at Broadway and 44th Street.

My coat and my ego were a bit tarnished as my husband rushed to help me up. To my surprise, two young men also stopped to help.

As I turned to thank them, one of them smiled.

“Hon,” he said, “it was totally worth it! Those shoes are fabulous.”

— Suzanne Schneck

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Illustrations by Agnes Lee

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The spring sales of modern and contemporary art often arrive in May with a steady drumroll of paintings whose estimates soar above $50 million — a sign of confidence in the industry’s roster of ultrawealthy collectors who trade them like financial assets.

Now that drumroll sounds like rain’s pitter-patter as the world’s leading auctioneers recalibrate for an art market rocked by economic uncertainty over the last three years and contend with new challenges, like tariffs.

Of the hundreds of artworks for sale this season (including pieces by Picasso, Basquiat, Magritte and Matisse) there are only a couple above the $50 million threshold: a 1955 Giacometti bust estimated in excess of $70 million, and a potentially record-setting work by Mondrian valued at about $50 million.

But without the spectacle of dinosaurs, bananas and cryptocurrencies in their big-name evening sales, the major auction houses are headed back to basics. It is a season of conventional offerings with very few headline-grabbing estates or deals at a time when these companies are suffering from layoffs; seeking outside investments; and weathering a 20 percent decline in sales within the industry’s broader downturn that has seen global sales fall to $57.5 billion.

“The upper reaches of the market over $5 million are very quiet right now,” said Jacob King, an art adviser in New York. “Material you would have seen in the day sale is now in the evening sale.”

Despite those challenges, the auction houses are still betting on themselves to raise mountains of money within a single week at Christie’s, Sotheby’s and Phillips in New York. Their combined estimate is $1.2 billion to $1.6 billion.

“Last season was a tough one because we had to put together the sales brick by brick,” Lisa Dennison, a top executive at Sotheby’s, said of the November auctions. “Going into the May sales, we did feel the pipeline flowing a bit more.”

Drew Watson, head of art services at Bank of America Private Bank, pointed out that some of the largest consignments of the season were announced in April, after President Trump’s tariffs went into effect — giving some reason for optimism. “You would expect that if people were really bearish about the art market right now that a lot of those high-end lots would not be coming to the market,” he said.

But the market remains soft, and new ultrawealthy collectors scarce, increasing the pressure on auction houses to perform. Here are six bellwether artworks in the evening sales that may indicate the health of the art market.

Alberto Giacometti

“Grande tête mince (Grande tête de Diego)” (1955), in excess of $70 million, Sotheby’s Modern Evening Auction, Tuesday

Giacometti was toward the end of his career when he created this bronze bust of his brother Diego, the artist’s studio assistant and muse. The sculpture has the highest estimate in New York’s spring sales and comes without a minimum financial guarantee from either Sotheby’s or a third party to ensure the artwork sells, as is typical with expensive lots. The seller, the Soloviev Foundation, a nonprofit founded by the real estate tycoon Sheldon Solow, stands to receive a bigger payout if the work sells for its estimate.

Solow, who died in 2020, acquired the work in 1980 from the Maeght family, which established the first private art foundation in France, the Fondation Maeght. The foundation is offloading the bust to support its philanthropies, which include the Metropolitan Museum of Art and Henry Street Settlement, according to its website.

“This one has always been the mother lode,” Simon Shaw, a Sotheby’s executive who helped arrange the sale, said of the Giacometti, which was cast during the artist’s lifetime. He described it as a “great sculpture in the season where it would be the most exciting thing available by some significant margin.”

Another cast of the artwork sold at Christie’s in 2010 for $53.3 million; adjusted for inflation, the price today would be $78.1 million, suggesting the artwork has appreciated very little in the last 15 years. Experts said the one being offered at Sotheby’s could sell for more because it is the only painted cast in the series.

Piet Mondrian

“Composition With Large Red Plane, Bluish Gray, Yellow, Black and Blue” (1922), about $50 million, Christie’s, Leonard & Louise Riggio: Collected Works, Monday

When the Barnes & Noble founder Leonard Riggio died last year, he and his widow, Louise, had acquired an immense art collection, championing blue-chip minimalist art and donating to nonprofits like the Dia Foundation, as well as modern paintings by masters like Pablo Picasso, Rene Magritte and Fernand Léger that hung in their Park Avenue apartment.

Louise decided to sell the apartment and consign nearly 40 artworks to Christie’s, including a Mondrian painting that will be the auction house’s most expensive artwork this season, with an estimate around $50 million.

Mondrian is considered a pioneer of European abstraction, thanks to his early experiments in color and geometry in the 1920s. These days, the financial value of his paintings is tied to the proportion of red covering the canvas, making the Riggio example a potential record-breaker. (A previous benchmark was set in 2022 at Sotheby’s, when a similar artwork sold to an anonymous buyer for $51 million.)

But that Mondrian was sold during the market’s height, leading industry analysts to debate whether the prestige of the Riggio name can overcome the economic uncertainty at play today. The auction house has also taken a large risk in providing a guarantee for all artworks, meaning that Christie’s will need to buy in whatever fails to sell.

“They did a big house guarantee and are having trouble selling it off,” said King, the art adviser. “It’s good material, but these are big estimates and there is a lot of stuff to sell.”

Olga de Amaral

“Imagen perdida 27 (Lost Image 27)” (1996), $300,000 to $500,000, Phillips Modern and Contemporary Art evening auction, Tuesday

A tapestry by the 93-year-old Colombian artist Olga de Amaral marks her first appearance in a major New York evening auction — the latest symbol that yet another under-known female artist has moved from the fringes of the marketplace to its upper echelon.

“She’s really a rediscovery, and finally coming out of the pigeonhole,” said Jean-Paul Engelen, a Phillips executive. “She’s no longer a craft artist or a Latin artist. She’s just an artist.”

Many of the other female artists featured this season are either bona fide auction stars whose work reliably sells for millions of dollars (like Agnes Martin, Georgia O’Keeffe and Cecily Brown), or rising talents with low estimates of $100,000 or less (like Danielle Mckinney, Emma McIntyre and Ilana Savdie). De Amaral stands somewhere between them, as an established artist whose value is still climbing after the opening of her first major European museum survey at the Fondation Cartier in Paris last October.

The seller of the tapestry bought the artwork directly from de Amaral in 1996. The artist has woven grids of linen covered in gold leaf to create shimmering abstractions. Three more of her artworks are in New York’s crowded day sales, including the 2006 tapestry “Imagen Paisaje I (Landscape Image I),” which has a high estimate of $1.5 million at Sotheby’s.

That Phillips has chosen a lower-priced work for its evening sales is a sign that the auction house struggled this season to pull significant consignments from sellers, according to experts. The company’s total estimate for the evening sales is far below its competitors and its top lot — a 1984 Basquiat painting with a high estimate of $6.5 million — is almost 90 percent less than the top lot offered in last year’s equivalent sale.

“In this market, what we have, we feel we can sell well,” Engelen said.

Jean-Michel Basquiat

“Baby Boom” (1982), $20 to $30 million, Christie’s 21st Century evening auction, Wednesday

Andy Warhol

“Big Electric Chair” (1967-68), about $30 million, Christie’s 20th Century evening auction, Monday

In 1985, posters promoting a show of collaborative paintings by Andy Warhol and Jean-Michel Basquiat featured the artists posing in boxing gear, as if squaring off instead of teaming up. Four decades later, Basquiat has knocked out all competitors — including the former champion Warhol — to become a bellwether in the art market, according to Christie’s global president Alex Rotter.

“If you asked me to name one artist, it’s Basquiat,” Rotter said. “Over the past five years, he has the broadest attraction to people at different price levels.”

After a prolonged buying frenzy for Warhol paintings, most prime examples now reside in museums and private collections that are reluctant to sell. His absence in the market allowed Basquiat to become a standard-bearer because his paintings and drawings still frequently circulate.

The appearance of Warhol’s “Big Electric Chair” will test if the ultrawealthy’s appetite for the artist has shifted. It is the lone Warhol piece estimated to sell for more than $10 million this season and shows Warhol’s fascination with America’s dark underbelly. “Big Electric Chair” was featured in the artist’s first European and U.S. museum surveys. In 2019, a multicolored version of the piece sold at a Christie’s auction just above its low estimate at $19 million.

The screen print is also competing in the same price range as Basquiat’s “Baby Boom” painting — one of the artist’s most accessible works from 1982, widely considered the best year of his career. The painting is an art historical sendup of religious iconography, reinterpreting the holy family of Jesus, Mary and Joseph as the artist and his parents.

Rotter said the Basquiat painting showed the evolution of the artist’s style. “It’s ’81 where the radical Basquiat comes out. It’s ’82 where he has confidence with the radicality.”

Carroll Dunham

“Bathers Seventeen (Black Hole)” (2011-12), $250,000 to $350,000, Collection of Barbara Gladstone, Sotheby’s, Thursday

Sotheby’s is holding dedicated auctions of artwork owned by two respected gallerists on the same night, a collection from the London gallerist Daniella Luxembourg with a high estimate of $41.1 million and a more modest group once held by Barbara Gladstone, with a high estimate of $17.2 million.

Gladstone, who died last year at 89, was a generational force in the art world responsible for boosting artists like Robert Rauschenberg, Keith Haring and Elizabeth Murray into the limelight. Her namesake gallery has continued after her death, with four remaining partners running six locations around the world.

There are only two artists in the dozen lots offered at Sotheby’s that are still represented by the gallery: Alighiero Boetti and Richard Prince.

Another artist, Carroll Dunham, disappeared from the gallery’s website only a few weeks ago. Gladstone had held more than a dozen exhibitions of Dunham’s artwork since 2004. (A spokesperson for Gladstone Gallery did not reply to requests for comment.)

That subtle change has brought some intrigue to the sale of his painting “Bathers Seventeen (Black Hole).” Although the work is estimated below his auction record of $591,000 in 2017 for “Integrated Painting Seven,” Gladstone’s personal ownership of “Bathers” could provide a boost.

“Works from her collection coming up for sale are iconic examples of each artist’s work, and each is a vital piece of contemporary art history,” said Molly Epstein, a senior partner at the advisory firm Goodman Taft. Gladstone choosing to live with these works “gives them even greater meaning,” Epstein added.