The Jewish Lives biographies published in an ongoing series by Yale University Press have typically functioned as succinct celebrations of Jewish achievement, covering a broad range of figures including Franz Kafka, Albert Einstein, Barbra Streisand, Steven Spielberg and Theodor Herzl.

But the latest book, released this week, grapples with a much knottier subject: Judah Benjamin, the eminent Southern lawyer and Louisiana senator who, during the Civil War, went on to serve as attorney general, secretary of war and, ultimately, secretary of state of the Confederacy.

“Judah Benjamin was the most politically powerful, and arguably the most important, American Jew of the nineteenth century,” James Traub, the author and journalist, writes in Judah Benjamin: Counselor to the Confederacy. “He was also the most widely hated one, not only in the North but in portions of the South. Benjamin does not deserve our admiration; but like some other figures who have yoked their lives to deplorable causes, he nevertheless deserves our attention.”

Traub, a senior fellow at New York University’s Center on International Cooperation whose previous books include a biography of John Quincy Adams, knew little of Benjamin when he first began the book — and found that was likely his subject’s preference. Benjamin left behind scant documentation of his controversial life, forgoing a diary and discarding written correspondence, perhaps aware that future historians would view him unfavorably.

Still, Traub had enough material to work with. Born in the West Indies, Benjamin grew up in Charleston and later moved to New Orleans, establishing himself as “the most prominent Jewish member of the bar,” Traub writes, and “by far the largest slave-owning Jew in America” thanks to his sugar plantation, Belle Chasse, where he owned 140 slaves.

Rather than embracing his Judaism, however, Benjamin largely eschewed his faith, despite never converting to Christianity. He married a Catholic woman, ate pork and did not observe the Sabbath.

“I think that Judah Benjamin wanted to efface his Jewishness as much as he could,” Traub said in a recent interview with Jewish Insider. “He wanted to be as not Jewish as he could. He wanted to succeed as much as he could, not among Jews but among Americans, among the people of New Orleans, among the people of the South. He did not want to be judged by Jewish standards. He didn’t want to seek solace in the Jewish world.”

“For him,” Traub added, “success meant success in a slave culture.”

Benjamin, a staunch defender of slavery, took that proposition to its extreme when the South seceded, going on to become an “indispensable counselor,” as Traub puts it, to Jefferson Davis, the president of the Confederacy.

After the war, Benjamin escaped to England, enduring a shipwreck on the way, and built a new life as a successful British barrister. “In a universe ordered by our moral imagination, Judah Benjamin’s life would have ended with a terrible reckoning,” Traub writes. “But the universe is not a movie. Benjamin died in 1884 wreathed with honors and probably quite content with the path he had hewn through life.”

In his new book, Traub, who is now at work on a biography of Hubert Humphrey, puts forth a proper reckoning, in spite of Benjamin’s best efforts to avoid close scrutiny. “Ambition makes men do terrible things, and he was an ambitious man,” Traub said. “He had to come to terms with slavery in order to achieve what he wanted to achieve.”

The interview is edited and condensed for clarity.

Jewish Insider: How would you describe your knowledge of Benjamin before you began writing this biography?

James Traub: Here’s what’s happened. Ileene Smith, who is the general editor of the Yale Jewish Lives series, as well as being a very celebrated editor at Farrar, Strauss, approached me about doing this, I think, because I’d written this biography of John Quincy Adams. If you had asked me then, I would have said, “Oh, Judah, Benjamin, he was that guy in the Confederacy.” That’s probably the sum total of what I knew. So I read the very good biography by Eli Evans written in the ’90s, and I thought there were so many things that were interesting. You know, the drama of assimilation for this poor kid from the South who made it to the highest echelons of American life, and then this moral drama of a person who, in effect, assimilated to the wrong side. For him, success meant success in a slave culture. I would say those two questions — one cultural and psychological and the other moral — made me think this is a guy worth writing a book about.

JI: He left behind very little documentary evidence of his life. He didn’t keep a diary and didn’t hold onto his letters. How did you make sense of this seemingly opaque man?

Traub: He kept a war journal, and when I discovered that, I thought, “Oh, this is going to be great!” But it was completely work-related. It had almost nothing human in it at all.

JI: What other sources did you consult?

Traub: Fortunately, there are certain parts of his life of which there were records, despite his own efforts. For example, his correspondence during the Civil War is completely available. Then there was business correspondence, of which there wasn’t a whole lot. Some of his correspondence with his sisters was available. What you wind up doing is just desperately gleaning everything that you can find. Then, part of the way I write biographies is I choose people who, I feel, stand for or embody things that I think are important and interesting. I’m somebody who probably stands at a greater distance from his subject than some other biographers do. I’m in the middle of writing a biography about Hubert Humphrey, and that is very much true. In the case of Benjamin, I already knew a fair amount about the slavery debates of the 1850s. When you think about him as a slave-holder, I wanted to learn everything I could learn about what it meant to own a sugar plantation. When you read about that, it really makes you sick.

JI: Did you speak with Benjamin’s living descendants for the book, if there are any?

Traub: He doesn’t have any. He only had one child. I don’t think the daughter had any children. There was never a grandchild that he dangled on his lap.

JI: Benjamin, by your account, was extremely reluctant to embrace his faith. He wasn’t religious. He ate pork. He married a Catholic woman. What accounts for that? Was it a form of self-preservation, or do you think he was simply uninterested in Judaism?

Traub: He lived in a world of very assimilated Jews. His mother kept the shop open on the Sabbath. His father, I think, probably was much more immersed in religious texts than Judah ever was. He was part of this very early Reform movement in Charleston in the 1820s. But when Benjamin moved to New Orleans, most of the Jews had married Christians. But it’s important to note that these were not Russian or Polish Jews who had come from a very pious background. They weren’t. Many of them were English. They’d come through the Caribbean. So the level of religiosity was lower than we imagine. 

But second, yes, I think that Judah Benjamin wanted to efface his Jewishness as much as he could. He wanted to be as not Jewish as he could. He wanted to succeed as much as he could, not among Jews but among Americans, among the people of New Orleans, among the people of the South. He did not want to be judged by Jewish standards. He didn’t want to seek solace in the Jewish world. Perhaps it was a repudiation of his parents. He wanted to go far. He didn’t want to be stuck in what he saw as that little world that he’d grown up in. So I think there’s also active repudiation.

JI: And yet he never converted to Christianity. Karl Marx, Benjamin Disraeli and Heinrich Heine were baptized. Heine described baptism as “the admission ticket to European civilization.” Why don’t you think Benjamin ever went that far despite all but disavowing his faith?

Traub: Like everything about the guy, it’s a mystery. Possibly he thought, “It’s pointless. My name is Judah Benjamin, I have thick, curly, black hair and black eyes and what people always describe as an olive or swarthy complexion.” The guy just looked completely Jewish. He may have thought, “I’m never gonna get away with it, anyway.” But it’s intriguing to speculate that there was some compunction in him. That while he would not honor his faith, neither would he explicitly repudiate it. But we don’t know. We just don’t know. 

JI: You present him as a true believer, but he did write a rather elegant repudiation of slavery during his time as a lawyer. Even if he was not speaking from the heart, his brief, as you write, “became a new cause célèbre for abolitionists.” How do you think he squared that, given that he owned slaves?

Traub: I try to tease this out. So, as you mention, in that case, he delivered this passionate address, which I think clearly draws on The Merchant of Venice, though he doesn’t say so. It’s hard to imagine that a person who would go to such lengths, even though we understand that he was an advocate, held the exact opposite belief — that in fact he viewed slaves as other Southerners did: sub-human. I tend to think that he was too intellectually sophisticated a person, especially having spent his life in New Orleans — where people of color did every single thing that white people did and there was this infinite gradation of people from 100% white to 100% Black, each with their own specified name —  that such a person could have held the simplified Southern view of Blacks as occupying the position, virtually, of livestock. I doubt that. 

But to say that is only to say that he may not have shared in the most viciously dehumanizing view, but it’s not to say that he entertained any active doubts about slavery. Because if he entertained active doubts about slavery, he couldn’t have lived the life he wanted to live. 

I just think ambition makes men do terrible things, and he was an ambitious man. He had to come to terms with slavery in order to achieve what he wanted to achieve. He could not have been a public figure. And so he was not going to let himself believe the thing which would have prevented him from living the life he wanted to live. Whatever complex thoughts he may have had about the nature of Black people did not prevent him from becoming a full-throated advocate for the South and for slavery when he came to the Senate and became a very important figure in those debates in the second half of the 1850s.

JI: Were there any details about Benjamin’s life that surprised you or that you found particularly revealing?

Traub: The previous biographies have been extremely coy about his sexuality, and so I didn’t really have any clue, when I started reading about him, not only that there were rumors but they may have been true. The rumors were spoken of in the biographies as if they were calumnies and nothing more. The fact is, when you think about the guy’s life — I don’t think it’s just our own modern reading, I think it’s the reality — that it’s perfectly possible that he was gay, and therefore, that this rebarbative quality he had of hiding everything was not merely because as a Jew in a Christian world he had to simply live in a self-protective way; he may have had something to protect that he thought was much more dangerous if discovered. 

The more you think about his life — he doesn’t have a child for the first 10 years of marriage. He has a child finally, and his wife deserts him. He continues to support them. He lives in New Orleans, where every man has a mistress, and he, who’s been abandoned by his wife, did not take a mistress ever. He has a very odd relationship to his wife’s much younger brother Jules, whom he utterly doted on, saving bits of food from fine meals to give to him. It doesn’t mean I think that he had a homosexual relationship with Jules, but it certainly does feel like if this guy is trying to either repress or not express his homosexual leanings in a way that would get him in trouble, Jules may have been one of the chief recipients.

JI: You mention in the book that Benjamin was offered a spot on the Supreme Court but turned it down — which brings to mind a counterfactual scenario in which Benjamin is perhaps remembered as the first Jewish Supreme Court justice well before Louis Brandeis was appointed to the court. Do you think there’s any way Benjamin’s life could have gone another way had he become a Supreme Court justice?

Traub: If he had been, he would have been one of the notorious people who decided the Dred Scott case. So we would have known him as a different kind of villain. But I wouldn’t have written the book about him. He wouldn’t have been an interesting figure. He just would have been a kind of successful Southern lawyer who went on to make terrible decisions on the Supreme Court. But it’s not his nature. I happen to have written two biographies of people who were asked to go on the Supreme Court. The other was John Quincy Adams, and Adams recognized that he didn’t have a judicial temperament. He did not want to have to make these fine distinctions and make himself a neutral arbiter. He was a vehement advocate. 

Now, I think, in the case of Benjamin, he was much more of a temperamental, neutral arbiter, but he also was a worldly person. He wanted to make money. He wanted to have a big life, and going on the Supreme Court would have put an end to that. It would have been the most dignified version of the life he ever could have imagined, but I think, to him, it would have felt like a coffin he had entered. 

JI: Did you feel any sympathy for Benjamin while you were writing the book?

Traub: I know people who have written biographies of really just horrible people, and it’s hard to understand how you can do that. I mean, Judah Benjamin stood for a set of principles that are despicable. But that’s not exactly the same thing as saying he individually is despicable. That’s a more complicated thing. There were many aspects of him that I admired and wish I could have known more about, and when I think about his retreat from Richmond [the capital of the Confederacy], and how everybody was flipping out, and this fellow was reciting Tennyson in order to keep his colleagues calm, and he never seemed to lose his cool, and when he had to escape all by himself in a hostile world, he was so resourceful. When he spent days and days on the open sea with the sun burning down on him, he was later able to write to a friend that “I never had a moment of indisposition.” 

There’s something astonishing about that. This is grace under pressure. This is what Hemingway meant by that. This is a resourceful man. That’s why I compare him to Ulysses. That’s why I say he didn’t have Judeo-Christian virtues. But he had classical virtues.