Raymond was born in Pittsburgh, Pennsylvania on February 3rd, 1944, to Alverna Yvonne Avery and John Henry Caldwell. He had 9 siblings: John Caldwell, Jimmy Caldwell, Joyce Quinerly, Joe Woodson, Melvin Woodson, Alvin Caldwell, Warren Caldwell, Lenard Woodson, and Rebecca Woodson.

Ray attended and graduated from Glad Stone High School.

Ray was a soft spoken, wise, understanding, kind- and open-hearted man. He would take the shirt off his back if you didn't have one, that was for everyone. He enjoyed singing, baking, grilling, dancing, and cleaning. He was very mechanical and always was prepared to help.

He was a giving person, always helping who he can at any given moment. Especially if he knew you. He was an amazing painter, he painted various places as he grew up, such as Harvard University and a few housing developments and apartments.

As he got older, in 2002, he started his daycare services. From that point he helped raise generations of children. "Don't make me get that soon" as "hard head makes a soft behind" were his sayings, that's how you knew you went to far.

He leaves behind his children: Mary Williams, Raezena Caldwell, Darnella Caldwell, Chante Hall, Ebony Clark, Nicole Hall, Raymond Caldwell Jr., and Nathalie Caldwell (daughter-in-law_ who will miss his dearly. He also leaves a host of grandchildren and great grandchildren who he loved dearly.

The family would like to extend a special thanks to Susie, Ronnie, and Mya for the compassion love and care they showed during his final days.