Jamie Vaughn McCaffrey-Boss

James “Jamie” Vaughn McCaffrey-Boss, born January 25, 2000 in Chicago, and then a resident of Oak Park, IL, Highland Park, IL, and the Dunewood Community in Bridgman, Michigan, passed away on December 9, 2023 in Chicago.

Jamie (he/she/they) was a 2018 graduate of Highland Park High School. As an artist, Jamie had a beautiful singing voice, an amazing talent for art and fashion, was a middle school trackstar, and a lifelong dancer. Jamie was in several performances of the Nutcracker with the NorthShore School of Dance; many friends remember times together that included dancing and singing. Jamie had a light and a determination that touched all those who knew her.

Jamie is survived by her devoted parents, Roger V. and Christopher A. McCaffrey-Boss; her adoring and devoted brother, Robert McCaffrey-Boss; grandmother Inge (Scheffler) Boss. Aunts and Uncles and Cousins include Alexa Boss Martin, Randy Martin, Erich and Ryan Martin; Aldrich L. Boss; Sandi Weber, Kay Weber, and Kim Weber; Owen McCaffrey, John and Michele Moore; many more cousins, friends, and honorary aunts and uncles.

Jamie was preceded in death by grandparents William A. Boss, Lois (Weber) Wiley, and Roger Longfellow McCaffrey.

In lieu of flowers, donations in Jamie’s memory may be made to Covenant House or Lambda Legal.

Friends and family with gather for a visitation on Sunday, December 17, from 4-8 PM at Drake and Son Funeral Home, 5303 N. Western Ave, Chicago, IL, 60625. A funeral service will then take place at Drake and Son on Monday, December 18, at 10 am with burial to follow immediately after at Rosehill Cemetery, 5800 Ravenswood Ave, Chicago, IL, 60660.