Brady laughed with the kind of spontaneous, delighted glee he had imitated so often during his years at Stanford, pretending to be Sam Winchester’s recovering friend, but so rarely felt. When you were the puppet master there weren’t many surprises, moments of startling amusement. Hearing Ruby reciting an exorcism, though? He could honestly say that was something he had never expected to hear. I knew it was worth being the one to do this. His laughter trailed off and he contorted his face into an exaggerated grimace, a mockery of the sympathetic face Sam had made so many times as Brady had explained his latest “relapse.” A mockery of the face Ruby had taught him during their lessons on gaining trust and then manipulating it. He shook his head slowly and pulled up the sleeve of his suit jacket to show her the binding mark on his arm. He let the sight sink in for a moment, then raised his hand and made a gesture that lifted her off of her feet and flung her back into the shadows of the alley. He followed at a slower pace, kept her pinned down with an absurdly minute degree of effort compared to what it once would have taken, and reached into her pocket, pulling out the phone, dropping it onto the ground, and then crushing it under his heel.
“You always did stress the importance of private lessons. The protégé-mentor bond. We wouldn’t want any interruptions now would we? Not during your final lesson.” He kicked the pieces of the phone to the side of the alley and took the gun out of his pocket. He leveled it at her and cocked his head slightly to one side, relaxed and amused in a way more appropriate to a meeting or an idle conversation than to the prelude to a murder. “I thought of taking you back to the horsemen, or to Lucifer you know,” he told her as he moved the gun between aiming for her head and her heart, seemingly trying to decide where he should shoot her. “I thought they might like the chance to torture the traitor for information.” He smiled, moved the gun to her head, and switched his expression into a parody of comforting reassurance. “But I’m a generous guy when things are going my way, and what they want, what they all really want, isn’t you. It’s Sam. And once you’re dead, once I find his mommy and burn her again, once I put his brother down like a dog, he won’t resist. He’ll walk to Lucifer with open arms. And,” he moved the gun to point at her heart again, “it will all start with you.”
His finger tightened on the trigger. “Goodbye Ruby. Thanks for that last laugh with the exorcism.”