This story is based on an idea that popped into my head after watching 'Time After Time'. This is not even remotely canon, just a wild idea.
Disclaimer: I don't own Supernatural or the Winchesters. I'm just having some fun with them.
After burning Cronus's body, Dean, Sam and Jody sat in the abandoned house talking. Dean was regaling them with his adventure in 1944 with Eliot Ness and how different he was from Kevin Costner's portrayal of him in 'The Untouchables'. Then he got on the topic of Ezra Moore.
"Man, you talk about a cougar! That woman laid one on me and told me being stuck in 1944 wouldn't be all that bad!" He was about to go on until he saw the look on Sam's face. "What?"
Sam bit his lip for a long moment before speaking, "Did you say Ness's contact was named Ezra Moore?"
Dean nodded, "Yeah. Dumpy, middle-aged. Think Bobby without a beard and in a skirt and heels. Why?"
Sam sighed, "It's just...Jess's great-grandmother on her dad's side was named Ezra and she lived in Canton, Ohio in 1944. What did she do for a living again?"
Dean shrugged, "She ran a men's clothing store. It's where I got that stuff," he pointed to the pile of clothing neatly laid out on the table."
Sam's face got even paler, "I remember Jess telling me that her great-grandmother used to run the family clothing store after her great-grandfather died in an accident."
Dean looked at him for a long moment, "Wait, you think Jess came from a family of hunters?"
Sam shrugged, "I don't know. I never noticed anything out of the ordinary whenever I went to her parents' house. But then, her dad had moved to the West Coast to attend college."
Dean was quiet. "Moore's a pretty common last name, I didn't think it meant anything."
Sam sat for a long moment, looking like he was gonna cry or be sick. Finally he stood up, "Excuse me."
Dean and Jody listened to his retreating footsteps before she turned to him, "Who's Jess?"
After Dean explained Jess to Jody, they talked for a while longer before Jody faked a big yawn and said she was ready to turn in. Dean took the hint (not that he needed one) and headed into Sam's room.
Sam was curled up on the blanket on the floor, Dean knew that his brother wasn't sleeping, his body was too rigid. He stood in the doorway a second, this was going to lead a chick-flick moment but if Ezra Moore was who Sam thought she was, a bunch of wounds had just been reopened and a lot of questions were being asked. Questions Dean wasn't sure either of them wanted the answers to.
He went to his brother and laid down next to him, hoping his presence would be enough to quiet the questions and fears that were coursing through Sam's mind.
Sam never said anything, but Dean didn't leave. He couldn't leave his brother hurting like this. He knew that even the thought that Jess might have been a hunter made Sam feel like he'd lost her all over again.
They lay there together all night, finding comfort in each other. In the morning, if Sam's eyes were red-rimmed and slightly swollen, no one said anything.
As they left Canton, Dean watched Sam in the passenger seat and prayed to a God who wasn't there that somehow it was all a coincidence and Ezra wasn't related to Jessica or that Jessica hadn't been a hunter, because if she had, he wasn't sure Sam would be able to take it.
It had always been his job to take care of Sam, and sometimes that meant shielding him from the things that could hurt him, and that included protecting him from the possibility that his beloved Jessica had possibly been a hunter and from all the what-ifs that he knew would haunt his brother forever if he let it, and Dean wasn't going to let it, not this time.