Oh, I think you'll find a lot of people who think the winner didn't deserve it, Russ. Actually, nobody "deserves" to win. You can't measure that. I've avoided talking much about the quality of the writing because you can't really measure that either. I do think that you're right that being "good" at Medium seems to have been a disadvantage.

The gold standard for an essay about death for me is David Sedaris' "The Spirit World." I had just heard him read it on MasterClass a day before I read the winning essay. There were some similar elements in the two stories: a family suicide following a mother's death and how the family processed these events. What makes Sedaris' essay superior (by about mile) is that it was sad, but funny, and devastatingly brave it its self-analysis. At the end, you go, "OMG. That was intense!" You also say to yourself, "What an interesting family!" We've all got families but few of them are worth writing about.

The MWC winner didn't work for me because the writer never tells you much about her grandmother except that she was "difficult" and mentally ill. There was nothing there that made me care about the people in the story. To be honest, I got bored and skimmed toward the end. At a certain point, it's a matter of taste and whether or not you've read anything better. You also have to factor in the reader's life experience. If you've led a quiet life, you're not easily impressed by the opening about the suicide as someone who's been around the block a few times.