Naw but Rowena was just being Rowena. Can't expect better from her. That's Crowley's own fault for being lulled by her. It's a situation of, "Fool me once, shame on you. Fool me twice..." It was the Winchesters who "exploited" Gavin's noble nature and encouraged him to sacrifice his life. They're "the good guys," so Crowley had reason to trust them to try and save his son. (ETA:  this is what I think Crowley's POV is, not my personal POV. Well, kinda sorta my personal POV, too :P). So