The Stoop · Hana Baba and Leila Day

This Christmas Will Be

December 19, 2024·23 min·2 clips

Greg Eskridge shares why he can't say 'I love you' back to his mother, despite her recent attempts.

The Stoop hosts Leela and Hannah present a holiday special focused on Greg Eskridge, a journalist they first met when he was incarcerated at San Quentin State Prison. Leela had been part of a team training incarcerated men to produce audio stories for KALW, a San Francisco radio station, and she interviewed Greg about Black men's relationships with saying "I love you." Greg grew up in Los Angeles with a mother who was dismissive and cold toward him. He ran away from home at age 10 to escape abuse from his sister's father and spent the next decade homeless or cycling through foster homes and boys' homes. At age 20, he was sentenced to 58 years plus two life sentences for second-degree murder, attempted murder, and assault with a deadly weapon. In prison, Greg found the holidays particularly brutal. Staff wore Christmas sweaters and discussed family plans, while inside there were no trees, lights, or candy canes. The few childhood Christmases Greg had on the outside became his most vivid memories, especially the taste of his Aunt Bee's sweet potato pie and visits to Uncle Rod's home, where he experienced unconditional love for the first time. Greg began participating in San Quentin's programs, including restorative justice, yoga, transformative meditation, and radio journalism. He produced stories about prison life and used recording as a vehicle to help other men process their feelings. In one piece for KALW's Uncuffed podcast, he explored the holiday blues that haunted him and other incarcerated men. Fellow inmates shared stories of cooking holiday meals for each other and apologized to their children for missing so many years. Donny Hathaway's "This Christmas" became Greg's emotional anchor, a song he played on repeat that transported him back to childhood memories of caroling and family gatherings. After 30 years, Greg's transformation was recognized by the parole board, and he was released from San Quentin in July. He recently visited his childhood home in Long Beach, driving past the site of his crime, which triggered intense anxiety that he managed through breathing exercises and positive self-talk. His mother seemed softer than he remembered, and for the first time, he felt genuinely at home. Now preparing for his first Christmas as a free man, Greg plans to buy a large tree, lights, bulbs, and tinsel. When asked what he wants for Christmas, he says being free is the ultimate gift. The episode closes with Donny Hathaway's "This Christmas" as Greg's soundtrack to his first holiday season outside.

As heard by us

A holiday story about freedom, memory, and what prison takes away.

The Stoop folds a holiday conversation into a quiet look at what Christmas can mean after freedom has been withheld. Hannah and Leela center Greg Eskridge's first Christmas as a free man after more than 30 Christmases inside prison, and the episode keeps circling the small…

Read the full review in PlayNext →

Why you'd press play

For when you want a Christmas story that reaches past the season.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from The Stoop