I've edited Gregory's background, his personality, his boss form, and information on his son and his lifestyle. I'd appreciate it if you left most of my edits alone unless you want to either add, or unless you think I wrote the wrong information. For this whole month I've based my studies on Rule of Rose, so most information I do put up is indeed true, and I'd rather you find a way to inform me first if you want to edit my information so that I see if your own information is true or not.
Gregory is complex, he is the man who pretty much started it all. The fact that his son died of an illness in the first place causes him to bring Jennifer into the picture, and while Jennifer is technically the main focus of the game, Gregory and Joshua's relationship was the main start of the game, and what pretty much causes everything to come forth.
Gregory was a poor man, who pretty much was trying to survive off of the crop of the land as well as what little he was paid for his services with gardening Mr. Hoffman's Orphanage. He was very fond of pea's, and had mostly pea's growing on his land. He made pea soup quite often, especially for Joshua. He sounds dull in the game, and sounds like a man who's life just went on. A type of life where not much happens, and the only differences in his life were the changes in his son, Joshua. In his diary, most of the pages were pretty much the same, that is farm was doing well, that his farm was doing well, and that his farm was doing well. Every now and then he writes a paragraph on Joshua's illness, how Joshua's feeling, how he's feeling about his son, and so on, but once every two pages about his farm doing well.
The fact that Joshua died of a sickness IS known, but no one is sure what the illness is, since it is rumored that Wendy herself had 'whooping cough', which was around in the 1900's, also causes me to believe that perhaps Joshua had something similar; the only difference between his and Wendy's would be that Mr. Hoffman had the money to help Wendy, while Gregory did not have that kind of money to help his own son. And in the end Joshua leaves his father all alone. Gregory is probably very much used to his sons company, and it must get awefully awkward and quiet, the fact that his one and only son dies, and he was unable to help him in any way, causes Gregory to start drinking, stop farming, stop going to the Orphanage, and he's in a state of... well... kind of like nothingness, where you just simply don't give a damn about anything or anyone.
Depressed, lonely, and miserable, he just wishes that he had his son back. It just so happens that while he's wandering outside of where he lived, he finds the wreckage of an airship. Within the many bodies of the dead, as well as possibly died down flames and rubble, he finds a survivor, probably injured. The child just so happened to have short brown hair, like his son's, and so the mind bending begins. Gregory had found Joshua! And they will never be seperated ever again! He takes the girl home, dressing her up in Joshua's old clothes, and keeping her trapped in the basement.
In his mind, that was definitely Joshua, and while he did trap the poor girl in the basement, he did take care of her. He fed her, gave her warm and clean clothes, as well as reading her stories. While he didn't notice this though, his 'son' was plotting 'his' escape.
While Jennifer did find the need to stay, since she knew that Gregory was just lonely and needed someone, she wanted a little more freedom than just the borders of the basement room. She escaped with her new friend, and suddenly the world crumbled around Gregory. His son was once again gone, this time... would it be forever?
No, here comes the blonde girl Wendy, or possibly in Gregory's eyes, another Joshua! Wendy visits Gregory every now and then, whether she tells him that she's Joshua, or whatever communication goes between them, Wendy obviously, according to Martha's letter to Doolittle, uses this time to 'train' and 'chat' with Gregory about something. She might have told him that she knew where Joshua was, and that if he didn't do as she said she'd hurt him in some way, she might have found other ways to persuade him into following her orders, no one could really ever know, but it got his attention, and from then on until the massacre of the Orphanage, Wendy and Gregory met up and discussed things.
After the last few months of Wendy visiting and such, on a dark and stormy night, the front door to Gregory's home is opened, and with the turn of his head, he see's Joshua. He's super happy! He has his son back... again! Gregory has changed though, somehow, he has markings all over his body, possiby from Wendy's abuse while 'training' him. Wendy is at his front door, tears in her eyes and rain on her wig, she's dressed as Joshua, and there's a moment where Gregory is wondering what is wrong with Joshua, and 'Joshua' tells 'his father' that the people of the orphanage threatened 'him' in some way. Gregory is now Stray Dog, and Wendy puts him on a leash and leads him to the orphanage.
Whether every child looks like Joshua or not, the Joshua by his side demands that he kill everyone in sight. And so he does, I mean, it is Joshua telling him this right? After he murders all the children, he ends up spotting Joshua talking to a girl, when Wendy takes off her wig, and Gregory pretty much realizes he's been used, he kills her too, and is in a weird rampage as half of him is trying to kill Jennifer, while the other half is asking 'Joshua' for forgiveness every now and then.
Jennifer has the choice to either kill him herself, or to hand him the gun and have him end his own misery.