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When Leopold walked out of Stateville Penitentiary he was 54 years old and had spent nearly two thirds of his life behind bars. Now he just wanted to live out his life quietly. That wouldn’t be possible in the center ring of a media circus, so he decided to abandon the USA and move to Puerto Rico. Once there he studied for a sociology degree at the University of Puerto Rico. He worked at various jobs, and also had royalty income; in 1958 he’d published his story, Life Plus Ninety-Nine Years.
Leopold also returned to his old passion, ornithology. Puerto Rico has a rich collection of bird life, with a total of 349 species found there, and he wrote a paper on them. A couple of years after his release Leopold met Trudi Garcia de Quevedo, the widow of a doctor from Baltimore. They married in 1961.
Leopold frequently returned to Chicago to see old friends. When there he would wander the neighborhoods near the university and visit the graves of his parents and two brothers. Most of those connected with the crime had died or left the city, but its notoriety lived on in books and cinema. Perhaps he dreamed of settling back in the old neighborhood, but some wounds healed only slowly. Every visit ended with his return to Puerto Rico.
He never forgot Loeb. In an interview in 1960, a year before his marriage, he told a journalist that he was still deeply in love with him. Several visitors to his home in Puerto Rico commented on the photographs prominently on display. One was Clarence Darrow - “The man who saved my life.” The other was Richard Loeb.
On August 20, 1971 Nathan Leopold was hospitalized due to diabetes. Ten days later he died of a heart attack with his wife at his side. After his death his corneas were removed and transplanted into two recipients.[38]