This is similar to the scene where Jessie finds out she once had an owner, as Leonard Weems is still sad over his son Randall's death.
Leonard Weems: Fluttershy106, why are you at my house?! I thought you got fired as substitute principal!
Me: To tell you the truth, it was my job. Also, why are you upset?
Leonard Weems: Because my son Randall was the same, he was my whole world.
(When he Loved me started playing, and a flashback shows the times Young Randall had with his dad)
Me: What's wrong Mr. Weems? Why are you crying?
Leonard Weems: My son died. All because he was murdered by Gelman.
Me: Mr. Weems, I didn't know.
Leonard Weems (in Jessie's sound clip): Just go!