From the photos, it appears this is the baby daddy, but it's unclear how the sherriff fits into the narrative. She's later in a wheelchair. If she's the mother, she was working very late into her pregnancy!
There's a baby, but neither Sam nor Dean looks very pleased at its appearance. Word is Darkness will take on the form of a specific entity, and a she to boot. Could it start out as a baby, and this one in particular? That wouldn't be a reason to smile.
It's Sam! How we've missed you, Sam. The brothers will be up against the Darkness, a pre-biblical foe who was defeated by God years ago. Sam is shown reaching out to God in the trailer. Can he be of help again? You'd think he might be angry the Winchesters released Darkness after it's already been banished.
Crowley likes to talk to young men in pairs, apparently. When the Winchester brothers aren't around, he'll find another pair of young men to take their place! What do you think he knows about the Darkness? Was she ever mentioned in his social circles?
Castiel seems to be pondering something. Is it a deal with Crowley? Or is he wondering where Sam and Dean are? We're guessing that he didn't imagine Crowley being so drastic with his mutha. Like, "Huh, I sure didn't see that one coming."
The King of Hell is back to his old evil self. But what's his plan with Rowena and Castiel? He's looking rather chipper. Whatever his plan is, it must be making him feel confident. Long live the King of Hell!