Dean Winchester crossed a line in Supernatural Season 14, Episode 19

Supernatural Season 14, Episode 19 delivered an intense episode, focused on the Winchesters’ next steps to deal with Jack. However, Dean Winchester certainly crossed a line.

I’ll start this by saying that there are spoilers in this post from Supernatural Season 14, Episode 19. If you haven’t watched the episode yet, you’ll want to check it out or read our recap for “Jack in the Box.”

Supernatural Season 14, Episode 19 delivered an episode focused on dealing with Jack. Dean fell into old habits, and at first, I was completely on his side. I got it. He was scared and despite all the character development in the world, that fight-or-flight defense mechanism doesn’t go away and it will never fully change.

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I’ll also admit that Dean is grieving. I’m willing to give any character a little leeway in resorting to old habits during grief. Mourning the loss of someone makes us all do stupid things. And “Jack in the Box” was a stupid thing.

When Dean Winchester crossed the line

Dean didn’t immediately cross the line in Supernatural’s “Jack in the Box.” As I mention, I was on his side at first. There was no way of dealing with this powerful nephilim and it was clear he didn’t know right from wrong. He thought turning people into angels and killing “heretics” was the right thing!

However, Dean crossed the line the minute he made it clear he would lie to Jack. He wanted Jack to agree to going into the box until they’d found a way to restore his soul. Just leaving it there would have been good and I could have been fully behind Dean’s actions. It would have been a temporary solution for a long-term, positive outcome.

And yet, then came the next part. Sam knew that there wasn’t a way to save Jack. Dean admitted that it would be a lie and then pushed his brother into being the one to tell the lie.

It’s no wonder Jack has put it in his mind that he can’t trust the Winchesters. Dean has a habit of doing this — or lying to people — when he can’t figure out the permanent solution.

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Had Dean been willing to actually search for a way to restore Jack’s soul, I’d have been 100% on board with the plan. But lying and just locking up Jack for eternity completely crossed the line.

However, it reminded me of when he held the gun to Kaia’s head to force her to help them. He was acting out of grief, anger, and fear. I think weeks later he would have completely regretted his actions but we’re not at that point of his thought development yet.

What did you think of Dean’s actions in Supernatural Season 14, Episode 19? At what point did Dean cross the line for you? What would you have preferred the Winchesters to do help Jack? Share your thoughts in the comments below.

Supernatural Season 14’s finale airs on Apr. 25 at 8/7c on The CW.