On March 13th, 1958, more than thirty-three years after he entered prison, Nathan Leopold was released on parole. He stepped out of Stateville penitentiary that Thursday morning into a crowd of reporters and television crews who swarmed him as he gave a short prepared speech, asking everyone to leave him alone.

“I appeal as solemnly as I know how, to you and to your editors and to your publishers and to society at large to agree that the only piece of news about me is that I have ceased to be news. I beg, I beseech you to grant me a gift almost as precious as freedom itself, a gift without which freedom ceases to have much value, the gift of privacy. Give me a chance, a fair chance, to start life anew.”

Despite his plea, this was not the last time his name would be in the headlines, and Leopold would have to spend the rest of his life trying to avoid publicity that continually reminded the world of his past crimes.

Nathan Leopold Speaking to Newsmen

Nathan outside Stateville reading a prepared statement to the press on March 13th, 1958

After a quick and queasy car ride, he made it to the home his old friend Abel Brown with a small army of newspaper reporters on his tail. He spent the night with the Browns, then without time enough away from reporters to even see the graves of his family members who had died while he was in prison, Leopold boarded a plane late on March 14th and left the city, for what many people assumed was the last time.

After a long flight and a car ride, Leopold arrived in Castañer, Puerto Rico. He had a job and housing lined up there with the Church of the Brethren, a Christian missionary service organization. Despite the conflict of religion, he became very attached, and would work on and off for this organization for the remainder of his life. In the early months of his release he worked with the doctors and nurses in a small hospital observing and assisting with surgeries, testing patients for parasites and taking x-rays.

In many frantic letters to friends and family he worried about his perceived inability and was nervous that the slightest problem would turn public opinion against him, sending him back to the penitentiary. He brooded often over the possibility of making a mistake and hurting someone, and what that would mean for his future. He also struggled with language, as the Spanish he had learned in textbooks was not what he found people using in everyday conversation in this, a small and often illiterate mountain community. This worry slowly eased as he caught onto the language and became more familiar with his surroundings and his life as a free man.

As he started to feel more comfortable with his place among the Puerto Rican people, Leopold began branching out beyond the small town of Castañer and in 1959 he moved to the city of San Juan, two hours away, and enrolled in the school of social work at the University of Puerto Rico. Despite the distance, he continued to be involved with Brethren activities when he could. He was very involved in fund-raising for a modern hospital and took special joy in dressing up as one of the Kings for Three Kings Day and handing out gifts to children. He also took up birding again as soon as he arrived on the island, attending the annual bird census yearly and starting to build up another ornithological collection in his home. In 1963 he published A Checklist of Birds of Puerto Rico and the Virgin Islands; an ornithological species guide for the islands.

To Leopold “life has always appeared as a perpetual battle against boredom.” He fought boredom, in his typical way, with both leisure and exhaustive work. For pleasure he went birding, deep-sea fishing and to movies with his new friends and coworkers. He jumped from job to job, getting intensely interested in a project for a while before dropping it for another, more attractive opportunity. He despised being in the same place for too long if he felt there was something more interesting to do elsewhere.

As someone who was given a life sentence, Leopold was obligated to remain on parole and under the supervision of a parole officer for five years. He was not allowed to leave the county, get married, talk to reporters, buy a car, move apartments, or make any big decisions without getting permission from his parole officer as well as the Illinois parole board. He quickly grew tired with this extension of the prison life he had thought was far behind him.

He longed to explore the world, to visit the graves of his family members and, essentially, to make up for lost time. Elmer Gertz observed that “he seemed to have an almost feverish desire to taste everything in life, whether good or bad; excess seemed to be his norm at times.” His prodigious mental activity and yearning to try new things were now in full force as he stood on the edge of freedom after so long in captivity. Though he made repeated attempts to secure an early release from parole, he wasn’t successful and had to wait his full five years for true freedom.

Soon after Leopold became comfortable on the island he began testing his limits, breaking the parole limitations he found so constricting. He drank, drove cars without a license, traveled where he pleased, visited brothels and used guns for hunting. Making sure to carefully conceal all forays from the rules and hoping to build up the best reputation possible, he was always very aware of the publicity he faced. In the beginning of his release he hid from reporters and avoided any event where people might snap a photo. When asked by a previous acquaintance if she could write a fictional account of his story, he wrote back declining permission, saying: “publicity in any form is very distasteful to me. It hurts me; it hurts the surviving members of my family; it makes it harder to find my place in normal living.”

In time he slowly began to move past this, and tried to establish a new identity for himself, that of a scholar with something important to contribute to the world. He carefully hid parts of his life from the public in order to maintain this altered image of himself. Though he repeatedly stated that he was religious, he remained an atheist all his life and though he did sometimes attended services for several religions, but he was more interested in the doctrine and ceremony than in any sort of belief. Another secret he continued to suppress was the ever-present specter his sexuality.

IMG_7169 (2)

Trudi (holding Sue Dogg) and Nathan in 1961

In Puerto Rico Leopold dated and entertained women and forcefully denied any connection to homosexuality. Only a few months after he came to Puerto Rico, Leopold met Trudi Feldman, an American widow and florist who lived on the island. They first got in contact at a Jewish seder and started pairing up on fundraising projects Leopold was involved in, Trudi lending her time and influence to help raise money for his various causes. And though he was hesitant at first, he soon came to enjoy her help and company. At the same time, he was hosting many women who had sent letters offering their hands in marriage now that he was paroled from prison. These women, more than half a dozen whom Leopold collectively called his “Fan Club”, came to Puerto Rico to spend time with the 53-year-old bachelor. He wrote to his friends of the amusement he got from these visits, and most of these suitors eventually stopped contacting him as he continued to turn down their proposals.

In 1961 Leopold married Trudi in a small ceremony away from the public eye and the couple only told their families after the event, for fear the news would leak and the press would again fill the newspapers with the events of 1924. They moved into an apartment in San Juan, where they lived together with the stray dogs they adopted. In May of 1961, Leopold graduated with a Master of Social Work degree at the top of his class and put his schooling to use among the native people of the island. He left his job teaching college algebra and carried out a series of social work jobs: visiting families in their homes, organizing charity benefits and connecting people to government services.

In 1963, after five years, Leopold was released from parole and immediately sought to make the most of it. He and Trudi flew to Europe and began raving to their loved ones about the sights. They followed this trip with one to Chicago to visit friends and family and the places where Leopold had grown up. In the coming years, he and Trudi became very well-traveled, taking at least one long trip to different countries every year. They saw the sights in Australia, Singapore, Fiji, India, Russia, Germany and countless others. Leopold seemed determined to see everything there was to see and try everything at least once, an attitude he’d maintained since his teenage years.

Leopold also took his release from parole as an opportunity to begin speaking his mind on a larger platform; he started giving lectures and publishing articles on the subjects of prison reform and capital punishment. Of the mind that people were rehabilitated in spite of prison, rather than because of it, he made a list of changes he would like to see initiated in American prisons in the hopes of moving towards a more therapeutic, rather than punishment based, approach to penology.

His friends and family were generally very pleased with Leopold’s adaption to life in the world outside the prison walls. To them, he had proven himself to be a kind, often selfless individual who worked tirelessly on many worthy causes and had a wide circle of friends, both in Puerto Rico and elsewhere, who held him in high esteem. It was noted by many that he could be arrogant, seemed attracted to publicity despite his denials, and that he seemed to think himself more important than others. But this vanity, when viewed in the light of his truly extraordinary intelligence and good deeds, was something that most people were able to overlook.

One other sticking point to some friends was a picture Leopold had framed and displayed in his home. Since moving out of the more communal Brethren housing, even after he started living with Trudi, a picture of Richard Loeb as he had been before the Franks murder smiled among the other framed photos of family and friends in his homes and apartments. Some friends, too disturbed, did not broach the topic with him, but to those that did, Leopold was said to merely shrug and remark that “the guy ruined my life. But he was also the greatest friend I ever had.” Trudi in turn simply said that it was not her place to argue; Loeb, as well as an ex-girlfriend from 1924 who was also displayed, were part of Leopold’s past, and he, after all, was a complicated man.


Nathan in 1971, a few months before his death

As the years wore on, Leopold continued living life to the fullest against the advice of his doctors. He smoked, drank, traveled the world, ate rich foods that his diabetes made dangerous and was little concerned about his health, often running on 3-4 hours of sleep a night after hours spent over his typewriter. Though always worried about the health of his friends and family, advising them frequently to rest and take care of themselves, he seemed to pay little attention to his own failing body.

In 1971 he spent almost the entirety of April in the hospital after a series of coronaries. Trudi diligently nursed him through his illnesses, though he was often irritable and demanding. While he was able to mostly mask his cantankerous mood in letters, in person, Elmer noted that “he agitated himself and everyone around him.”

After being released from the hospital with strict orders to rest, in June of 1971 he took a trip to the States, his oxygen tank in tow, for what he planned to be a month-long vacation around the country. Days into his trip he fell ill at the home of Elmer Gertz. In the middle of the night he was taken to the Michael Reese Hospital, where he recovered for 20 days, visited almost daily by Mrs. Gertz and his brother Sam.

Talked out of continuing his vacation or trying to fit in his various other plans, he nevertheless flew first to New York before returning home to Puerto Rico. He insisted on travelling soon after he got back and visited friends in Castañer from August 14th-18th. He was ill on his return and the morning of the 19th Trudi took him to the hospital where he continued to disobey the doctor’s orders. He remained in the hospital for ten days, Trudi and her sister Anita visited him with home cooked meals daily and the many friends he’d made in his thirteen years on the island came to see him as well. Leopold died in his hospital bed on the evening of August 29th at the age of 66, with Trudi at his side. His body he willed to the University of Puerto Rico Medical School and his eyes were donated to an eye bank.

Elmer Gertz, who had been his lawyer and one of his closest friends, remembered receiving calls from media stations all night after Leopold’s death, asking for a statement about his former client. In his autobiography, Elmer remarked rather candidly on Leopold’s desire for positive attention and admiration that, “Nathan would have been pleased that, in his death, he was still news.”

Trudi, in an interview with the press after Leopold’s death, declared that: “His whole life was spent atoning for one mistake and now the Leopold story is finished.” In the years after his death she seemed to go back on this statement and began planning to write a tell-all biography about her deceased husband. She also began fighting other authors who were working on books, threatening to sue Hal Higdon if he published Leopold and Loeb: The Crime of the Century, which explored the events of 1924 in detail. She never completed her book and the Leopold story continued living on in crime books, legal anthologies, fictional accounts and in the memories of those who knew the enigmatic man himself. Despite Leopold’s efforts to rehabilitate his image, today he is still simply known as half of the infamous Leopold-Loeb teenage thrill killer duo.