The Long Journey Home
Nathan Osborn reflects on 44 years inside the walls
Meet Nathan Hunter Osborn, the longest-incarcerated person in Central California Women’s Facility (CCWF). Osborn is 65-years-old and a well-built transgender man with a neatly trimmed goatee. He exudes a quiet confidence as he takes a seat for our interview in 512’s dayroom. His muscular frame disguises the fact that Osborn has been incarcerated for the last 44 years. He is close to tripling his 15 to life sentence.
Osborn was arrested in 1981, the year I was born, the year CD players were first introduced to the world and the year MTV revolutionized music and pop culture. He was sentenced to 15 to life, has been to board 11 times, and flipped the tables on the board commissioners once. Yes, he literally turned the tables over in the Board of Parole Hearings room.
He took a circuitous route up and down all the level IV women’s prisons in California. He began his time in the California Institute for Women (CCWF was not built then) and spent 14 years in Southern California. In 1995, he made his way to CCWF, then went across the street to Valley State Prison for Women (VSPW) for a Segregated Housing Unit term. Finally, in 2012, when VSPW became a men’s prison, Osborn returned to CCWF. His journey across California prisons was fraught with 98 disciplinary write ups, fights and trouble.
“In the beginning of my time, it was a struggle. In the 1980s, we were told we were never going home and that killed all of my hopes and dreams,” said Osborn. His goals in prison became being a thug and using all criminal thinking one can muster up. He filled his days embracing the stereotypical convict lifestyle and wreaking havoc.
This all changed in 2017. “A woman changed my life,” Osborn beamed as he described his turning point. Osborn met a girl, fell in love, and began to love himself. They were two broken people when they began their time, but wanted better for one another. They remain together and are still very much in love.
Osborn freed himself, but that was just a start. Years of bad behavior cannot be rectified in mere months. He began attaching himself to positive people, set small goals for himself, enrolled in the Medically Assisted Therapy program and started his healing process.
Kaylee Weisenberg, an incarcerated individual and a friend and mentor to Osborn said, “There are very few people I have met and wanted to see go home more than I want for myself. Osborn has been in prison longer than I have been alive. I have known him for many years and have watched him transform into an amazing man. I will never forget his raw emotions as we had our first conversation about healing, life and freedom. I can’t wait to see what he will do with his opportunity. He is an inspiration to so many.”
Yes, he backslid, he fell down, but he also got up, dusted off his knees, and started again. “I had to surrender,” said Osborn.
Today, Osborn resides in 512, is an integral part of the Insight Garden and is getting ready for the world beyond these gates. You can find him gardening and beautifying the yard for all of C yard to enjoy. He ties gardening, falling in love, and earning his freedom together.
“Everything worthwhile in life needs work. Gardening, a healthy relationship, and earning my freedom all need watering, care and attention,” said Osborn. Whether it is 60º or 100ºF, Osborn is unfailingly digging and planting in his white tank and blue jeans.
Osborn plans on attending a truck driver program to expand his job opportunities. He wants to be a truck driver, where solitude and hard work are essential. “Like gardening, this will give me the opportunity to reflect on where I was, where I am now, and where I want to go,” said Osborn with a huge grin on his face.
When asked for advice to young lifers, Osborn replied ruefully, “Your greatest failure is the beginning of something amazing. Never give up on your hopes and dreams.” He lives by this motto and hopes to encourage those deemed as failures. With his story of inspiration and hard work, anything is possible.
He was at rock bottom, but he used each stone that was blocking his path as a stepping stone to success. At the end of the pile, he found he was the biggest boulder of all, and when he got out of his own way, the sky was the limit for Osborn.
Osborn went to board on April 4, 2025 and was found suitable for parole. The longest prison sentence served at CCWF is coming to an end.
Osborn is both nervous and excited to leave prison after 44 years. Technology is a hurdle he is anxious to tackle. Pagers were in when Osborn was out. Driverless cars and facial recognition were seen on “The Jetsons,” not on the streets of San Francisco. These are new and fascinating technology Osborn will see for the first time, and for the first time, our longest incarcerated resident at CCWF will see the outside world.
