Can we just talk for a second about how Ruby manipulated Sam? She didn’t go straight at him in the beginning. She took her time and really observed him. Didn’t take her long to figure out the best way to get to Sam was by pretending she could save Dean, but that’s not all she did. She was a tough, beautiful, wise-cracking, junk food-eating badass in season 3. Do you suppose it was just a coincidence that description also fits Dean perfectly? I think she was working Sam from two angles- “I can help save Dean and hey, btw do I remind you of anybody? Maybe someone you love more than anything?”

That becomes even more obvious in season 4 when she was Ruby 2. With Dean gone, she really stepped up her game. In the flashback sequence of “I Know What You Did Last Summer”, she sat back and watched Sam hit rock bottom and then stepped in. Then she openly manipulated him by continuing to act a lot like Dean did, even calling him Sammy. She was TRAINING him ffs. Training him to use his powers, just like Dean would have once trained him to use his weapons. It was masterful how she wormed her way in.

You have to give Ruby credit for being extremely clever. She always knew what button to push and that button was always marked “DEAN”.