Which is funny, cuz so do I.

In Exodus 13x22, Dean IS indeed shouting to his "generals"

DEAN: Lucifer! Let's go! Cas, Ketch... show 'em how it's done.

(Side note// Lucifer looks completely bowled over by that, actually.)

Dean ushers Ketch and Cas to go. But one of these things is not like the others. In Dean's mind, perhaps Ketch (maybe Lucifer?) have EARNED their way back, but...

Cas is rift trauma.

Strategically, it makes more sense for Cas to stay with them and fight: with Sam, Dean, Gabe, Lucifer. Just like strategically, it made sense for Cas to be Lucifer's overseer at the camp and on the bus. Cas was, after all, temporarily stronger than Gabe. (Aside// For that matter, it makes sense for Jack to stay, too.)

BUT ANYWAY. My point is! Up till now, Cas was the literal bodyguard/bouncer of the group.

SEE:

But here, Dean can't handle that.

Not this time.

It's why, in the script, it's a more obvious beat with Dean and Cas. Cas gives Dean a fond look because Cas realizes that it's not a strategically sound move.

Cas realizes this, but he's relenting.

(Speculation// I think this implies that, on some level, just like how in the Tombstone script Cas ask, "Are you okay?" to Dean, Cas is on some level aware that his previous death... hurt Dean terribly.)

ANYWAY. Sweet detail here: Despite relenting on being willing to go through, Cas hangs back a bit, arm outstretched, making sure Jack, Mary, Bobby, and Charlie go before him:

Jack. Mary. Bobby. Charlie.

Only then does Cas go through.

(Which sets up a pretty nice contrast against Ketch and Lucifer, who are both, despite "being on the team," chomping at the bit to come through the rift mostly for their own safety.)

When he gets through, Cas immediately goes to check on Rowena, too:

///

ASIDE re Lucifer: I was talking the other day about how ultimately Dean's time as Demon Dean results in increased forgiveness towards those that manipulated/used him (i.e. Cain, Crowley, Amara specifically.) Which is why the Claire-Randy parallel… ...yadda yadda big, understanding hearts.

ANYWAY, I posited that it wouldn't surprise me if Dean is naturally/instinctively the type to forgive even the most horrific figures in life: maybe even figures like Azazel, Lucifer.

I feel like his treatment of Lucifer and Ketch above lends some weight to that idea. Specifically, the script and reaction shots make you wonder if Dean was indeed shaky on the whole "leave Lucifer behind" plan.

Was Dean cutting Lucifer some slack? I don't think it's out of the realm of possibility! He's forgiven others who killed and tortured loved ones, after all.

In the last bit of the script, there's a moment where Dean seems to be struggling with it pretty intensely, even:

Despite everything that happened, Dean wonders if maybe that was the wrong choice.

And Dean's morals... tend to have some unfortunate weight.

///

Other notes:

RE: Getting everyone home. Sam too was busy stressfully doing a head count:

SAM: "Mom, Bobby. Charlie, you're with them."

But when Lucifer gets held up by Sam, we see Dean looking, again, a little unsure about this?

Lucifer looks Dean's way too, like he's APPEALING to him. It's an interesting moment to me, because this episode starts out with Dean being the one screaming for Gabriel to, "Kill (Lucifer) him!"

Lucifer at first steps in front of Gabe to protect him. (The fear and cowardice ofc will win out after he's injured and after Gabe dies.)

After Gabe dies, Dean is horrified, but he's also seeming a bit guilty to leave overall. I do wonder about the complexities of Dean's inner conflict there...

The series plays so often with this seesaw of Dean being totally rigid (for example in this episode: saying KILL Lucifer, and then shown torturing people for information a la Endverse-style with Cas), but he's also... surprisingly bendy with extending mercy after ppl have put in effort to help or better themselves...

even Lucifer?

It's so lovely (and so very human).

EDIT: All that to say that, despite appearing very comfortable levying judgment, and like everyone in the series, despite having overcorrective moments of trauma/fear where he backslides and divvies out judgment according to a FIRM (hunting) code...