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Everyone forgets that Nathan Leopold died a free man. The first part of his story is familiar enough: He and Richard Loeb were two intellectually precocious teenagers from Chicago’s wealthy German Jewish elite, and they read too much Nietzsche and started thinking they were supermen. Loeb, the sociopath of the pair, fixed his heart on committing the perfect murder, so together they kidnapped and killed fourteen-year-old Bobby Franks. They were caught, tried, and would have been hanged if their defense attorney had not been the great Clarence Darrow, whose closing statement was such a triumph of courtroom rhetoric that the Cook County judge sentenced them to life in prison instead.

That, for most people, is when the curtain comes down. But the story of Leopold & Loeb didn’t end in a Chicago courtroom in 1924. It didn’t even end at the gates of Stateville Penitentiary in 1958, when Nathan Leopold was released on parole after serving thirty-three years, six months, and two days. (Loeb was slashed to death by a fellow inmate in 1936.) It ends in Puerto Rico in 1971, when Leopold died of a heart attack after thirteen years of freedom, most of which he spent doing hospital work in a little town called Castañer with the Church of the Brethren, a Mennonite-like Protestant sect. He also married a widowed florist named Trudi Feldman, to whom he’d been introduced at a friend’s Passover Seder.

In all its externals, Leopold’s life followed the arc of a basic redemption story. He felt remorse for what he had done, unlike Loeb, who only regretted that he had been caught. He devoted his time in prison to service. He reorganized the prison library, he participated in an experimental test of a new malaria drug as both a lab tech and a lab rat (the latter at some risk to himself), and when a young Italian man arrived at Stateville newly blind after a mishap during his last hold-up, Leopold learned Braille so he could teach the man to read. He expanded the course offerings at the Stateville prison school by writing stacks of new lesson plans and grading the papers himself.

He also began to pray. Leopold was Jewish, but he formed a friendship with the Catholic chaplain, Fr. Eligius Weir, a Franciscan. Weir was humble, personable, and also very brave—-he once marched unarmed into the middle of a prison riot, against the advice of the frantic guards. He and Leopold had many long talks about repentance, and his Christian charity was a nicely symmetrical counterpoint to the other great influence on Leopold’s moral development, Clarence Darrow, a famous agnostic . Leopold credits Weir with teaching him to pray:

I think it might have been easier if I could have got it off my chest, could have shared it with someone, could have told someone how I felt. But there was no one on earth to whom I could tell it; there was only God. Father Weir had persuaded me to pray regularly, and since I started doing so some twenty or twenty-five years ago, the day has not passed that I have not prayed to God for the repose of Bobby Franks’s soul, for the assuaging of the grief of his parents, when they were alive, and for forgiveness for myself.

That quotation comes from Life Plus 99 Years , the prison memoir Leopold published shortly before the parole board approved his release. They had turned him down before, and his memoir was written partly to demonstrate his rehabilitation to the board and to drum up popular support for his cause. That may be one reason the book is not well regarded—-who can trust what a man says when his freedom depends on saying the right things? Leopold intended to write a second, less propagandistic memoir, suggestively titled Reach for a Halo , but it was never completed.

Without Reach for a Halo , all we have to go on in evaluating Leopold’s post-rehabilitation mindset is his book, the testimony of his friends, a few news articles about his Puerto Rico days, and scraps of personal correspondence. They paint a mixed picture. Leopold admitted to friends that his service projects in prison were undertaken largely to stave off boredom. Even people who were fond of Leopold described him in his later years as prickly, arrogant, and irrationally hostile to authority. Visitors to his home were shocked to see that he kept a framed photograph of Richard Loeb in his bedroom. When a reporter asked his wife what she thought of the picture, and the adjacent one of Leopold’s high school girlfriend, she shrugged and said, “Nate wants it. They were part of his life. And let’s face it—Nate after all is complex.”

He never gave up the bad habit of being intellectually provocative for provocation’s sake, or taking unseemly delight in being shocking. That had been his greatest contribution to the folie à deux that got him into trouble in the first place. Leonard Lyons records this anecdote from 1963:

One night we dined with the Leopolds and one of the guests was a San Juan specialist in physical medicine. The doctor inquired about Leopold’s work as an X-ray laboratory technician, and they talked in professional terms. Then somehow the conversation veered to the news story about Sherri Finkbine, the mother who had flown to Scandinavia for an abortion because she feared that the thalidomide she had taken would produce a crippled child.

Leopold said she was absolutely right and argued for the futility of condemning an unborn infant to life as a cripple. The doctor was unconvinced.

“Don’t you believe in euthanasia?” Leopold asked.

“No, I believe in life,” the doctor said.

“But in this age of the bomb?” Leopold asked. “I wouldn’t want to survive.”

The doctor pointed to Leopold’s cigarette: “Then why do you smoke?”

Leopold leaned back in his chair. “Suppose I could live X number of years smoking,” he said, “and exist X number of years plus eight by not smoking. I prefer just X number of years.”

The doctor discussed the rate of increase in life-span. Once, he said, the life-span of man had been 33 years. Leopold’s comment was: “Christ died at thirty-three.”

But none of that proves his gestures of penance were all hollow. He had three job offers lined up when he applied for parole—translating memos for a friend’s import/export business, working as an X-ray technician on the West Coast, and the Puerto Rico job—and he chose the only one that would involve being surrounded by people of faith. Perhaps he had discovered in prison that he enjoyed the company of believers. He wrote to his lawyer of his admiration for the Church of the Brethren:

The pastor who preceded the present incumbent was a Puerto Rican, who spoke no word of English. And yet the young volunteers serving at the Brethren Service project attended every service . . . although they could not understand a word of what was said. Once I asked a young volunteer just why he sat through so many hours of a service he could not understand. Somewhat surprised by my question, the young man replied that he was bearing his witness. A wonderful concept, and one I have meditated upon a great deal in the years that I have passed since I asked the question.

The question of whether Leopold ever achieved redemption is ultimately God’s business and not ours, but if he did find God, then maybe Bobby Franks’s murder really does deserve to be called “the crime of the century.” We know that Leopold was seduced by Nietzsche and then saved from death by Clarence Darrow’s closing statement, and it’s possible that he found faith, in his own way, by the end. Damned by romantic nihilism, rescued by liberal humanitarianism, redeemed by belief—it certainly would have gratified Leopold’s outsize ego to learn that he could plausibly claim to have lived the 20th century in miniature.

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