Late in the summer of 1938, as the Nazis escalated their persecution of German Jews, Ilse Hesselberger and her daughter, Trudy, traveled from Munich to Milan to visit relatives.

From there the daughter went on to the United States, and safety. The mother, who was a Protestant by faith but Jewish by ethnicity, made her way back to Germany, where she had been known for years as a socialite who gave lavish parties.

But upon her return, Ms. Hesselberger found little to celebrate in Munich, a city that played a key role in Hitler’s rise to power. Identified as a Jew under the Nazi race laws, she soon was forced to sell her country estate. She also lost an art collection that included a painting, “Portrait of a Young Man with a Quill and Sheet of Paper,” that she had bought in 1927 and is now viewed as a master work.

Nazi officials then pressured her to help pay for construction of a camp that would later be used to send Jews to concentration and death camps.

Historians said that Ms. Hesselberger was assured that she would be spared resettlement if she paid, but that promise was a lie. In November 1941, just weeks after turning over 100,000 reichsmarks to help finance the camp, she was placed on the first train from there, which went to German-occupied Lithuania, where she and many other Jews were murdered by the Nazis five days later.

Now the portrait that Ms. Hesselberger bought in 1927 is to be sold at auction to benefit one charity that aids Holocaust survivors, among others, and a second that helps the visually impaired. After acquiring the painting at some point, the German government returned it earlier this year to Ms. Hesselberger’s estate, which has consigned the work to Sotheby’s.

Experts there have concluded that the painting, which has been attributed over the years to a number of Italian painters, is actually a portrait by Agnolo Bronzino, a leading artist of the Florentine Renaissance who is thought to have created it in roughly 1527.

The work shows a figure holding a quill in one hand and seeming to point with the other to a few lines of words inscribed in Latin on a creased sheet of paper.

Sotheby’s estimates that the work, which will be included in a January sale of old masters in New York, will sell for $3 million to $5 million. Works by Bronzino are not often on the open market, according to Sotheby’s, which said the last offered at auction, a painting called “Portrait of a Young Man with a Book,” sold in 2015 for more than $9 million.

“Discoveries of this caliber come once in a career,” Elisabeth Lobkowicz, a vice president at Sotheby’s and a specialist in old master paintings, said in a statement.

When Ms. Hesselberger bought the work, she was an heiress to a sewing machine fortune and the wife of the owner of a leather factory in Munich, Franz Hesselberger, who died in the mid-1930s. As a Protestant with Jewish roots, she would likely have felt some isolation, said Janne Weinzierl, who researched Ms. Hesselberger’s life and contributed to a collection of writings about the history of German Jews in Munich that was published as a book in 2008.

“As a rule, the Christian communities offered no protection or help to the ‘non-Aryan’ Christians and the Jewish religious community did not feel responsible for them,” she wrote in that volume.

Trudy Hesselberger, it turned out, had escaped just in time. Two months after her departure, German passports held by Jews were invalidated. The Kristallnacht pogroms took place a month after that. Then in December the Nazi authorities forced Jews, who had already been required to register assets worth more than 5,000 reichsmarks, to sell property, businesses and stocks to non-Jews, usually at low prices.

Experts said Ms. Hesselberger is unlikely to have known about plans for the camp in Milbertshofen when she was summoned to a Nazi office in 1941 and asked for money. The request was probably more of a demand, said Dr. Andrea Löw, the deputy head of the Center for Holocaust Studies at the Leibniz Institute for Contemporary History, in Germany.

“She didn’t have a choice, ” Dr. Löw said.

Many Jews were compelled to finance their own demise, she said, and the Nazis often offered false hope to induce cooperation. Indeed, Dr. Löw added, multiple Jews, all of whom were eventually sent to camps, contributed to the Milbertshofen facility’s construction.

Despite the promise that Ms. Hesselberger would be spared, Nazis placed her on what Ms. Weinzierl said was the first train from Milbertshofen to remove Jews from that area. German government records state that she was deported to Kaunas on Nov. 20, 1941. According to Yad Vashem, she was killed there on Nov. 25, 1941.

By then the Bronzino painting had been acquired by the Reich chancellery with help from Gerdy Troost, known as Hitler’s favorite interior designer. It was included in the collection of the Führermuseum, part of an extravagant complex that Hitler had planned for his hometown of Linz, in Austria, but which was never built.

After the war American forces found the painting stored inside an Austrian salt mine and it was later turned over to German officials. For the last several decades, it has been in the possession of the Federal Republic of Germany. It hung for an undetermined time in a federal building in Bonn, but by early 2022 had been moved to a building in Berlin used by the German Parliamentary Society.

Several years ago David J. Rowland, a lawyer from New York who specializes in recovering artworks looted by the Nazis, heard about a painting in Germany that might belong to the heirs of Ilse Hesselberger. He spoke with a lawyer for the estate of Ms. Hesselberger’s daughter and soon his firm, along with lawyers in Germany, began researching the work.

In early 2022 the German government turned the painting over to the estate after concluding that its confiscation as a result of Nazi persecution was very likely. The estate consigned the painting, then attributed to Jacopino del Conte, to Sotheby’s. When it arrived at the auction house in March, it was covered by layers of dirt and thick yellow varnish.

But Ms. Lobkowicz and Chris Apostle, another old master specialist with Sotheby’s, believed there was something exceptional underneath. They sent a photograph to Carlo Falciani, a professor of art history at the Accademia di Belle Arti in Florence and an expert in Florentine portraiture, who concluded the work was by Bronzino.

Among other clues, Mr. Falciani wrote in an email, the hands were drawn the same way that they were in Bronzino’s youthful portraits and that “the clear light and the stereometric form of the figure in space are exactly those of Bronzino.”

Dr. Elizabeth Pilliod, the head of the art history program at Rutgers University-Camden, who has written about Bronzino, said that Sotheby’s asked her to look at the painting and that she too is of the opinion that it is an early Bronzino.

While researching the painting’s provenance, Sotheby’s said it had traced it back to Sir William Temple, a 17th century figure who had advised King Charles II and been a mentor to Jonathan Swift.

The auction house began looking into Ms. Hesselberger’s history, too. Lucian Simmons, Sotheby’s worldwide head of restitution, said that at first he found very little, adding: “It really seemed that the Nazis succeeded not only in killing her but in killing her memory.”

Eventually, he learned enough for a picture of Ms. Hesselberger to emerge, Mr. Simmons said, but he was not able to gain any insight into what, exactly, had caused her to turn back to Munich in 1938 when her daughter proceeded to America.

Ms. Weinzierl said that while conducting her research, she spoke on the phone with Ms. Hesselberger’s daughter, Trudy, who by that time was in her 90s but had clear memories of her mother.

Ms. Hesselberger had returned to Munich in part because of a romantic relationship she had there, Ms. Weinzierl said Trudy had told her. She also said that in 1941 Trudy and her husband had paid about $200 to obtain a visa to Cuba for Ms. Hesselberger.

“But it was too late,” Ms. Weinzierl said. “Before this could reach her she was deported.”

Colin Moynihan

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