The episode “Somepony To Watch Over Me” is loved, hated, or in between when it comes to the fandom. Some fans hate the episode for Applejack’s supposedly out-of-character actions, others think she was perfectly in character when episodes like “Bridle Gossip” are taken into account, and some of them don’t care either way and just like or dislike it. But whether or not Applejack was out of character, it’s possible that episode told us more about the death of AJ’s parents than any other episode has.
The premise of the episode is that Applejack becomes overprotective of Applebloom after leaving her alone at the farmhouse. However, at the beginning of the episode, Applejack is already worrying about leaving her sister alone to the point of unjustified paranoia. Although this scene is played for laughs, it takes on a darker meaning when it is connected with the deaths of Applejack’s parents. Is there another, more serious, reason she’s worried about leaving her sister alone? Perhaps Applejack’s parents died in a farming accident. Since they work on a farm, that seems to be the most logical explanation for their demise. Building on that, maybe it happened in such a way that Applejack felt she could have saved them. In that case, her worries about leaving her little sister alone wasn’t just paranoia. She was being tormented by memories of her parents’ death and didn’t want the same thing to happen to her sister. Big Mainctosh doesn’t seem nearly as concerned as AJ, but he also doesn’t stop her from returning to the farm. This implies that he knows that neither of them could have done anything about the deaths of their parents and it’s useless to dwell on it. But he knows that Applejack won’t listen to him if he says this. He also knows that seeing that Applebloom is totally fine will snap his sister out of her overbearing state. The fact that there actually was an accident, although it wasn’t fatal and it was Applejack’s fault, was an unlucky occurrence he hadn’t considered. As the episode goes on, Applejack becomes increasingly obsessed with her little sister’s safety. Among other things, she forces her to wear a helmet and puts nets underneath the apple trees. These similar forms of protection might be hinting that Applejack’s parents died as a result of an apple-bucking accident or some other mishap that involved something falling. Perhaps the barn, which is notorious for being destroyed, collapsed on top of them and they ended up trapped or fatally injured. Applejack, being young, might have run to get help when she saw her parents were in trouble, but was deterred for some reason. She might have been told later that she couldn’t have saved them anyway, but she didn’t necessarily believe this.
On to another theory: Did Applejack’s parents die while making a delivery? If the fire swamp is anything to go by, the Apples sometimes have to go through pretty dangerous places just to deliver pies. If the delivery system is recent, it’s unlikely, but let’s say it isn’t recent. Perhaps Applejack’s parents went to make a delivery to a distant town and had to go through a dangerous area. While there, they were set upon and killed by a creature, possibly a chimera. If that was the case, it makes sense that Applejack knows how to handle these creatures. After finding out that her parents were killed by one, she would have felt the need to train herself. Naturally, Applejack feels guilty because she’s under the impression that she could have saved them if she had convinced them to stay home instead of risking their lives. Why did she tell Applebloom she trusted her to stay home alone at the end of the episode? Because even though she doesn’t want history to repeat itself, Applejack has accepted that she really had no control over what took her parents’ lives. Protecting Applebloom to an ridiculous point won’t heavily impact the future, just like trying to talk her parents out of making the delivery didn’t prevent them from dying.
Next: Fluttershy’s Parents: The Evidence of “Dragonshy” and “Putting Your Hoof Down”.