I think that's the same with pretty much any writing/storytelling contest. I've won many contests (not here on medium), and lost many more and every single time I've won, I've been surprised by what the judges picked. One piece was one I almost deleted because I was embarrassed by how bad I thought it was. Things I've whipped up in 10 minutes have won substantial cash prizes while other pieces that I've worked my ass off on, spending countless hours on every detail, have been passed over without a second thought.