"You're right, nothing is fair, the fact that youre gonna be walking out of California isn't fair. Suck it up.". He grabbed Lindsey's bag and put it on the curb. He could do this, they were gonna hurt Sam. He started lifting Lindsey's guitar our if the trunk, trying to keep his anger up. He knew Lindsey was a corporate guy, he's not the one that made decisions about crap that would have involved Sam...but he could have told dean before now. Or been more cooperative about getting Sam away from that place...or something...
Depends on how pissed off/panicked Lindsey is