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‘Divide and conquer’ is one of the oldest strategies in the book. And it’s simple, really – while one of them might not see through an enemy’s plot, they were usually quite attuned to when the others were going off the rails. Castiel knew that the times he’d walked away from Dean Winchester were the times he’d walked into Crowley and Metatron. He…should have known better, but more importantly, these foes would not have approached if the Winchesters were standing right there to warn him of what a bad idea it was. At first, he thinks it’s just him – his own weaknesses making him a vulnerable target, an easy dupe for a schemer who is steps ahead of him.
But that is not the case. Because he’s seen how Sam and Dean keep each other from going off the deep end, and what happens when you leave them alone. The strongest he’s ever felt, the most right, was, strangely enough, during the Apocalypse when he was weakening. Because, yes, people were counting on him, but they were counting on each other. Team Free Will. He bet everything on that, and Sam and Dean did, too, and…it paid off. Beyond any reasonable hope, their trust in each other was not in vain.
But on their own…send Dean to hell, and Sam teams up with a demon who leads him down a merry path to demon blood addiction. Castiel hadn’t understood the compulsion until he met Famine, but when he did, he realized how nearly hopeless it had been to get through to Sam during that. Let Sam be justifiably upset over the perceived betrayal of Gadreel and stopping the Trials, and Dean winds up teaming up with Crowley and getting the Mark of Cain. Even Meg apparently met Sam first, during some adventure when he was not with Dean. Granted, Castiel had liked Meg, but he recognized that demons could be very pragmatic that way. They sensed vulnerability, and went in for the kill. You just…can’t leave the Winchesters to their own devices. They need each other. Castiel has always felt protective of the Winchesters, but it’s this understanding of how they save each other, keep each other human, and save him from his own pride and hubris that leads him to the conclusion that protecting them must be his primary goal.
And then…he slips up. Again. He forgets that ‘keeping them safe’ does not mean ‘shutting them out’ and he goes after the Nephilim (his crime) without them. He should have known better. If he’d just trusted them, worked with them, the situation could have turned out…differently. Not that they abandon him. No, of course not…they just show up on his doorstep in the place he’d run away and supposedly hidden with the best warding he knew – to tell him that Lucifer is on their heels and all is in vain. Not that they put it that way. They’d never give up, not them. But…he can see the accusation there. The ‘Why didn’t you trust us?’ and ‘Why couldn’t we have worked together?’ and the fear of ‘What if it’s too late to save the world this time?’
But now that they're here, maybe they can. Somehow.