Well, you can always find fluff in Oscar stories if you need a quick cure!
But as far as Dean’s concerned, he comes off as a bully a lot, but it has a lot to do with the situation at hand.
Dean is a hunter, and if they find a supernatural creature (like poor Bowman), it’s his job to find out if it’s dangerous, and if it is, it usually falls to him or Sam to put a stop to the monster. He would never cause harm intentionally to an innocent (like all our Oscar stories), but he also can’t just let them go on their way.
In the case of Bothering Bowman, the story took a turn for the harsh because Sam got hurt, and as far as they knew, it was Bowman’s fault. Until Sam woke up, they had no way of knowing Bowman was innocent of any wrongdoing. Dean did the only thing he could, in his mind. Contain the threat, find out more. Once they found out Bowman was an innocent, they released him and brought him back home (with quite a few more shenanigans along the way).
Like Garth says about Dean in the canon TV show–