|Family|| Evelyn Leonard (wife) †|
David Leonard (son)
Daniel Leonard (son)
|Portrayed by:||Dean Cain|
- "Greg wasn't anything powerful or extraordinary. Not a Hunter, Prophet, Witch, Man of Letters or whatever else there is. Just a regular guy that helped people and loved his family. Maybe that's why God chose his boys to be powerful and extraordinary. They came from something that was good and simple."
- ―Craig Rolden
Greg was very good friends with Craig Rolden ever since the two were in high school together. They entered the Police Academy roughly one year apart from each other and eventually became partners. Greg fell in love and married Evelyn who became a schoolteacher and they ended up having two sons, David and seven years later Daniel. His friend became a big part of their family and ended up serving as a surrogate uncle for his sons. Greg made sure to teach his boys the value of being good and respecting authority. He shared with them his love of being able to protect and how important his duty was for the people in their town. His older son David admired his father and surrogate uncle and wanted to grow up to do police work just like them. He instilled into his younger son Daniel of how guns weren't toys by pulling him aside and giving him a lecture which his son kept close to him into the present day.
For years they lived a typical surburban family life up until his wife died of pneumonia. Greg was devastated but remained strong to raise his two boys without her. He rose to become an esteemed and popular member of his community. People wondered when it would be that he would become sheriff. His son David tried to become a police officer but wasn't able to pass in the Academy like he did. The best that he could do was become a security guard. Greg saw that his son felt he was a failure and tried to tell him that it wasn't the end. That he could still rise to be something great and that he still had time. As for Daniel, he was proving to be quite the smart and accomplished student and thought he could actually end up in federal law enforcement.
However he never got to see either of their futures as he and Craig responded to a call of a robbery. A man was robbing a jewelry store but they intercepted him before he could make a clean getaway. He pulled his gun out and shot wildly at him and managed to fatally hit Greg. This left his son David, then 22, to have custody of his 14 year old brother. His partner Craig became driven to find the robber and bring him in, which he eventually did. Craig and his sons received a semblance of closure when the man was given a life sentence.
His sons went on with their lives until the events of the Apocalypse unfolded. Their lives changed forever when the angel Joseph of The Powers descended upon his son Daniel. Now his son David serves as that angel's vessel and Daniel is the current Heavenly Saint.
Both his sons keep what he had taught them close and have even shared some of his sayings and teachings with those around them.
Facts and Trivia
Gregory seems to share many similarities to John Winchester on how they both lost their wives when their sons were young and have taken to teach them about their respective lines of work.
The name Gregory is derived from the latin word Gregorius which means watchful or alert. Ironic as Gregory Leonard was a dedicated police officer.