So this Naomi has been controlling you...
...since she got you out of purgatory? - Yes.
Wanna guide me out of purgatory out of the goodness of your undead heart.
- More or less. What's in it for you?
I'm hopping a ride. What?
It's a human portal, jackass.
Only humans can pass through.
- He's a vampire. - The reason I'm topside.
You had to do what you had to do. But you're out.
And Benny's still breathing. Why?
Listen, Benny, everything you done for me, I will never forget.
- End of the line? - End of the line.
God built a series of tests. When you've done all three, you can slam the gates.
- I didn't pass the test. - But I did. I'm doing the rest of them.
- Slow down. - No. You said, nuking hell.
That's how I get out, how I go home. I need this to be over.
Kevin?
I know what you're up to.
Working with them, those Winchesters?
Dead end, Kevin.
Not here.
Not here either.
Give up.
I'm in your head.
As well as everywhere else.
Last time you irked me, you lost a finger.
Imagine what will happen this time.
Kevin, open up.
Kevin?
Whoa, whoa. Jeez, what's going on? What's with the SOS?
It's him.
- It's who? - Crowley.
What about him?
He's in my head.
He's in your head.
- Do you know what that means? - It means we need to up your anxiety meds.
Kevin, you're dreaming.
If Crowley knew where you were, he'd do more than mess with your head.
Hey, where's Garth?
On a case. Or the dentist. I don't know. I haven't heard from him.
What couldn't you say on the phone?
Would you put the frying pan down, please?
I translated the second trial from the tablet.
You crazy prophet, you. Nice work.
And if Crowley's in my head, he knows.
- He's not in your head. It's okay. - He's definitely not in your head, Kevin.
You're stressed. Just stay with us, all right?
What's the second trial?
An innocent soul has to be rescued from hell and delivered unto heaven.
- What? Unto.
That's how God talks.
Rescue a soul from hell? Like, actually go to hell.
How do you get a soul unto heaven? How do you even get a soul out of hell?
We're gonna need an expert.
Winchesters.
- What happened to the hot chicks? - I'm out of here.
Maybe not.
I ain't got nothing.
Bite me.
Well, then how about another owie?
You know, wouldn't it be a lot easierjust to tell us how to enter hell, uh, uninvited?
It's secret.
We promise we won't tell anyone.
No. Wait. I can't.
It's forbidden, man. They gonna kill me.
Please.
All right, look...
...for a price, y'all can be smuggled across hell's border.
- By who? - Rogue reapers.
They got secret ways in and out.
And not just hell.
The veil, heaven.
Rogue reapers smuggling people?
People, souls.
So, what, they're like hell coyotes?
Now kill me. Come on, man.
Better death than Crowley.
Mm-hm. Good point.
But first, you're gonna tell us everything.
Ajay?
Need to talk to you for a sec.
- You know my name? - And what you do.
- We wanna do business. - But you are mortal. Flesh and blood.
But if we wanted across the border, into hell...
Visitor's pass.
No one wants to get into hell.
But could a coyote like you do it?
It's possible. But I have special skills.
I have overhead. It would be pricey.
How pricey?
You two are resourceful. One day you will owe me a favor.
- You say that like you know us. - Of course. You're the Winchesters.
Sorry. Have we met?
I am the reaper who took Bobby Singer to hell.
Bobby in hell?
We burned his bones. Once we did that, it was over, end of story.
- Hmm, not necessarily. No, no, no.
Bobby was on the good side of things, and good guys go to the penthouse.
Usually. Mostly.
Depends on who you know, what palms get greased.
If you're on the king of hell's no-fly list, no way you cruise the friendly skies.
Crowley.
Okay. Let's do this. How much for two tickets down and three back?
- Dean. - What?
Come here.
What the hell are you thinking?
You heard the guy. Bobby's in hell. We're gonna spring him.
We've gone over this. I have to do the trials.
This is Bobby we're talking about, Sam.
Let's face it, you have not exactly been up to full speed lately.
We got one shot at this. We can't miss.
I'm not gonna miss.
I'll bring him back.
I'm in. Just me.
- Follow me. - Wait, wait, wait. How does this work?
Not to fret.
He'll be back in exactly 24 hours' time.
Return for him then.
Take my hand.
And it gets creepier.
- So this is hell? - Not at all.
This is purgatory.
What do you mean purgatory? This isn't what I paid for.
- I booked the hell tour. - Whoa, whoa. Winchester. Detach.
This is hell-adjacent.
Been down this highway many times before.
Follow the stream to where three trees meet as one.
Where they meet there are rocks, between the rocks is the portal.
- The portal? - A back door to hell.
Trust me, it'll work.
- So you're not coming with me? - Heh, don't be ridiculous.
Smuggling a mortal across the border is risky enough.
But gate-crashing a Winchester into hell? Seriously blows.
No.
I'll be back in 24 hours, precisely.
Be here.
It's a good thing you brought that.
It is not an easy place.
Yo, Kev, it's me.
Kevin.
I believed the closet would be safest.
- Safe from what? - Crowley.
He's in my head, Dean. And if he's in my head, he knows where I am.
You know, we should move out, you know, find another place.
Jeez, Kev, would you chill out, huh?
Have a burger.
Come on. Don't lose it on me now, dude.
There you go. That's it.
Just tell me when this all ends.
Because that's the only thing I wanna hear.
No, like I told you before, this isn't going to end.
Look, man, other guys, they got it easy, you know?
It's all backyard barbecues and bowling teams.
But you and me, we gotta carry a little extra weight.
I can't take it.
Yes, you can.
Hey, look at me.
This whole thing sucks. I know.
But you suck it up.
And you push through because that's what we do.
And when you get onboard with that, the ride is a lot smoother.
French fry?
I'm gonna be in my room.
Let me know when there's a good day.
That's my pie.
Hello, Ajay.
It's been a while since we chatted. Too long.
Pizza? Extra anchovies.
Anything you want to get off your chest? An update?
Um, no. No, not really.
As you may recall, patience isn't one of my virtues.
Well, I don't have any virtues.
But if I did, I'm certain that patience wouldn't be one.
So sure there's nothing weighing on you?
Nothing, say, about making a deal with the Winchesters?
Sir, I know better than to attempt that.
My operative saw you leaving with Sam Winchester.
Oh. Oh, Sam Winchester.
Oh, yes. That's a possibility.
You're trying my non-patience.
Sir, I was just doing what I do.
As you are more than aware, I do occasionally moonlight as a freelancer.
You do not freelance with them.
What did Sam want?
Well, uh, actually, it's, uh, starting to come back.
- He may have wanted to get into hell. - My hell? Why would he wanna do that?
I don't know. I swear. My job, I don't ask questions.
And what time is Mr. Winchester due back from hell?
Uh, I'm picking him up in...
Well, now 17 hours.
I see. Anything else?
No.
I swear.
Hmm.
That's one fare you won't be collecting.
It's a rabbit hole.
This is nuts.
I'm innocent.
Help me.
Eddie? Eddie? Eddie.
Eddie.
You came. I knew you would.
I've been praying for forever.
I'm not him. I'm sorry.
You came. I knew you would.
I've been praying for forever.
You came. I knew you would.
I've been praying for forever.
Bobby?
Get the hell out of here, you black-eyed son of a bitch.
- What? Bobby, it's Sam. - Yeah, and I'm Elvis.
- Move your ass. - Bobby.
- Get! - It's me.
Okay, damn it.
If it's not Sam, then how do I know about you and Tori Spelling?
- What? You're a fan.
Yeah. Or, uh...
Okay, what about your free pedicure at the Mall of America?
You made Dean swear to never tell another living soul how it changed your life.
Sam?
I'm sorry, Sam, but you're the 200th Sam I've seen today.
That's how they screw with me.
Just endless Sams and Deans, all wearing the same black eyes.
Wait a minute. What the hell are you doing here?
Please don't tell me it's what I think it is.
No, no. No, Bobby, I'm good. L...
I'm here to get you.
You don't belong here, Bobby.
And we're getting you out.
Am I the only one who sees the urgency of this?
- Sir. - Something is going on.
My hellhound has been killed.
Winchester, jumbo size, is trying to break into the mother ship...
...and that prophet of theirs is madly translating away.
- Add it up. - I will, sir.
Where did we get you?
A temp agency?
I need Kevin Tran and I need his half of the tablet.
Apparently, his half has the good stuff...
...where mine has the acknowledgments and "about the author."
- It will be done. - It had better be.
Find that kid.
Hey, Kevin. Come in here and grab some of these eggs.
Kev, come on, man, you can't hide in there forever.
Where the hell have you been? What happened to being scared?
I am scared. So I made a preemptive move.
You made a what now?
I can't sit here with the tablet like a sitting duck...
...and Crowley breathing down my ass.
Getting rid of the tablet just takes off some of the pressure.
- Wait. Getting rid of it? - Temporarily. I hid it.
What? Where?
If I tell you where, it's not hidden, is it?
Kevin, tell me where the damn tablet is or I swear to you...
You'll what, Dean?
Kevin!
Kids. So cute when they're little...
...then they turn into teenagers and the party's over.
We haven't been formally introduced, Dean.
My name is Naomi.
Oh, I know who you are.
And I know what you did to Cass after he got out of purgatory.
After I rescued him from purgatory, you mean?
At the cost of many angels' lives.
You screwed with his head and had him spy on us.
Well, it is true that I have spoken with Castiel many times.
Trying to reach out to him, trying to help him.
Dean, you must have noticed how purgatory changed him.
I mean, he's been unstable in the past...
...but I was shocked at how damaged he is now.
Stop, okay? Don't try to spin this.
You think I don't know that you told him to try and kill me?
Yeah, I suppose that is how he would hear it.
When I learned of the angel tablet, I did tell Castiel to get it at any cost.
That's my job...
...to protect heaven.
I'm a warriorjust as you are. What would you expect?
And now Castiel is in the wind with a hydrogen bomb in his pocket and I...
I'm scared for all of us.
Save it.
See, I don't trust angels, which means I don't trust you.
And yet you haven't warded this place against us.
I know.
You're hoping Castiel will return to you.
I admire your loyalty. I only wish he felt the same way.
I know you don't wanna believe it, Dean, but we're on the same side.
Shutting the gates of hell, bringing Castiel in from the cold.
Take a moment. Think about what I've said.
Oh, I know you've been doing business with Ajay.
He did mention, didn't he...
...that his way into hell is through purgatory?
I knew you'd wanna know.
You see, we can be of help to each other.
- You know where the hell you're going? - Yeah, we're almost there.
Get back. Get back, get back.
We gotta get out of here.
- They're messing with you. - Don't listen to him. He's not real.
- Bobby, get away from him. - We gotta go now.
You knew somehow, right?
I took a chance.
Fifty-fifty.
What do we do now?
Ajay? Hey.
What the hell is this?
All right, well, don't get all pissed off.
Purgatory.
Balls.
Let's go.
Yeah. Yeah, it's me.
Know. I know, man. It's been a long time.
I mean, I wanted to call, I did. I just, uh...
I thought it might be better if I didn't.
So good to hear your voice, Dean.
I mean that.
- How you been? Well, you know...
...I get by.
I guess I let you down, huh?
I'm just happy as hell to hear from you.
You might change your mind about that.
Why? What you mean?
Benny, I gotta ask you a favor.
It's a big one.
So how many more of these trials after this?
Just one. I don't know what it is, though. Not yet. Kevirs still translating.
Well, you saw back there in hell, I ain't got a lot of rust.
Just feels so good to be back in action again.
Might be handy you having me around to help.
Bobby, I'd love that. Believe me.
The thing is, for this trial to be completed, your soul has to enter heaven.
And besides, if that werert the case, we burned your bones, Bobby.
There's nothing to tie your spirit to Earth.
Yeah. Yeah, well...
You know, I always figured that'd be the end of it.
You know, just a hunter's funeral. Then, zip, nothing.
And I was okay with that.
Imagine my surprise.
I guess if there has to be an eternity, I'd pick heaven over hell.
Yeah, because there's nothing screwy going on up there.
I wish I made the rules.
I'II, uh, do my part, get to the end of this, but I ain't exactly the retiring type...
...so if you idjits figure out a way to spring me...
Yeah. No, of course. That's, uh... Yeah.
Well, then let's get topside.
What's going on, Sam?
This is it. This is the place. I'm sure of it.
- Where your cabbie's supposed to meet you? - Yeah. At exactly now.
So he's running a little late.
See, that's the thing. He was very specific, Bobby. To the minute.
And if he doesn't show?
We got no way out.
If you want nothing to do with this, I completely understand.
Wow, when Dean Winchester asks for a favor, he's not screwing around, heh.
Sending you back is the last thing I ever wanted to do.
- I know, I know. - But my little brother is stuck down there.
This would be the brother who wants to kill me?
You got access to the place.
By "access" you mean getting beheaded?
Yeah, you're right. It's too much.
It's not like I've exactly been there for you lately.
What?
Oh, come on, Dean.
You know I love a challenge, heh.
You're serious?
Hey, he's your brother.
I say let's do this.
I owe you.
You don't owe me nothing.
Truth is, uh, I could use a break from all this.
Has it really been that tough?
I'm not a good fit, Dean.
Not with the vampires, and for sure, not with the humans.
I don't belong.
And after a while...
...that starts to wear on you.
Right. Heh.
Cry me a river. Like you need to listen to this, heh.
Well, when you get back up here, we're gonna fix all that, okay?
- When I get back? - Yeah. You find the portal...
...and you ride out of purgatory with Sam, just like you did with me, okay?
Soon as I send you back, I'm gonna haul ass to Maine.
I'm gonna be waiting there for you when you get topside.
Yeah, that sounds like a plan, chief.
Let's get on with it.
You sure about this?
Not my first rodeo, man.
Thank you.
Ugh, come on, you wimp.
Dean spent a year in this place?
Running and fighting. All day, every day.
Must have been hell on you, not being able to get him out all that time.
You did try?
Bobby, Dean and I had an agreement, okay?
I know that agreement.
I taught you that agreement.
That's a non-agreement.
I get the feeling a lot must have happened while I was gone.
Sam.
Bobby, no, no! Wait, wait, wait!
Why are you here?
Dean sent me.
Dean? Not my Dean.
He's a buddy of Dears, Bobby.
- A buddy? - A good buddy.
A frigging vampire?
Well, you two really went off the rails while I was gone, didn't you?
You saved my brother's ass a few times down here and I respect that.
And now I'm trying to save yours, heh.
You know, I'm a disgrace to my own people.
Yeah, this is the spot.
- The seam that gets us back up top? Mm-hm.
Is that it?
Yeah, that's it.
You boys remember what I told you?
Yeah. All right, Bobby, here it goes.
We get to Earth, I release you, it's an express straight to heaven.
No time for goodbyes.
I already said goodbye to you once, Sam. Didrt seem to take.
No reason to think I won't see you again, somewhere down the road.
Yeah.
But if they give me a rocking chair up there, I'm raising hell.
All right. Come on, Benny, it's your turn.
- Hurry up. Benny.
And still working with the Winchesters.
- Hurry. - Time for you to go, Sam.
Benny?
Go on. It's me they want.
Go on. And just make sure you tell Dean I said goodbye.
I was never any good up there, anyway.
Benny, wait.
Benny?
Purgatory, right? A real garden spot, ain't it?
Yeah, heh.
Did you get them out?
- Only Bobby. - What?
I mean, that's fantastic about Bobby.
Dean, look, Benny, uh...
...he got us out.
A bunch of vamps showed and he used himself as bait.
I get the feeling that even if that didn't happen, he didn't wanna come back.
I'm sorry.
You're probably right.
So, uh, Bobby, how'd he hold up down there?
He's good, all things considered.
- And ornery as hell, of course. - As he should be.
Let's put that old man where he belongs.
Yeah.
- The hell? Hello, boys.
Bobby Singer. I'd know you anywhere.
Let him go, Crowley. He doesn't belong in hell.
He does if I say he does.
He's inflicted untold damage on my kind.
From where I sit, actually, hell's too good for him.
Really?
What?
Oh, come on.
Let me see if I've interpreted the situation correctly.
The Winchesters have freed an innocent from hell...
...to which you are wrongfully trying to return it.
Siding with them, Naomi? You don't know those two.
Before they're done, we'll both be locked away.
I'm just hoping they lock you away, dear. The rest, I'll figure out.
Bureaucrat.
You're fighting outside your weight class.
Don't call me a bureaucrat.
I told you you could trust me.
- What the hell was that about? - I'll tell you later.
Let's get this trial done.
Sam?
What? What?
- Talk to me. What? - It's okay. It's okay.
It's okay, I'm fine.
It's done.
So tired of this, aren't you, Kevin?
The fear, the hiding.
I know I am.
It's a dream.
It's just a dream.
Kevin Tran.
It's been a while.
Thought you could elude me forever?
There's always a way.
If you can't find one Tran, find another.
Your mom, she didn't wanna give you up.
Quite a pain threshold, that one.
But even she could only take so much.
She never would have told you.
Moms are like that, aren't they?
So we killed her and got your address off her smartphone.
No!
What you people never seem to understand is that you are nothing.
Fleeting blips of light.
I am forever.
You okay?
Yeah, I'll live.
I buried Benny.
But I didn't burn his bones.
After he said he'd try to get you out of there, it just didn't seem right.
- I know you got no use for him, but... - No, no, no, you know what? I get it.
I do. He's, uh...
He's a little different from what I thought.
So go ahead and leave the door open, if you want.
Let's go check in with prophet boy and see where he stashed that tablet.
Kevin? It's us.
Kevin.
Kevin?
He's gone.
He took all his stuff. His notes.
I saw this coming.
Finally freaked.
The little geek made a run for it.
Yeah, but where?