Talking Smack 415

Family: Jamie the Great’s Nephew Shai Gilmore on Being Raised by the Green–Roseman Crew

Debbie Mink & Jamie Roseman Season 6 Episode 42

In this episode of Talking Smack 415, Jamie the Great and I sit down with someone very special: Jamie’s nephew… but also kind of her son… brother… all rolled into one — Shai Gilmore.

Shai’s story blends resilience, humor, and the fierce love that only family  can provide.

He takes us back to when he was about 4 years old in Florida, where his Pop-Pop stepped in when life got complicated. Shai opens up about:

  •  Growing up with a mother in recovery
  •  Losing his father to a car accident
  •  Realizing, at just 4 years old, that “something wasn’t right”
  •  Becoming everyone’s favorite Green (sorry, Jamie)
  •  Navigating identity with a different last name
  •  High school chaos, college radio, and  pranks
  •   What it felt like when he supported Jamie while she battled cancer 

It’s sweet. It’s funny. It’s a little messy.
 And above all — it’s a reminder that family is family is family.

We’re launching this episode for the holidays because Shai’s name literally means “gift.” So here it is: the gift of Shai — his laughter, love, and light — for your holiday season.

Whether you’re in the Bay Area, Florida, New Jersey, or navigating your own family story, this episode is for you.

Grab your earbuds or hop in the car and press play.  


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