Judging by the sympathetic response Show was getting during the promo segment with Stephanie, it looks like it's working just fine to me. Trips, Stephanie & Orton are being such world class dick that it's generating support for any babyface they target. Since returning, Big Show has gotten the biggest babyface reaction he's gotten in a very long time, maybe even ever. Also, as someone pointed out, Big Show's actually a pretty good actor and he's especially good at selling sadness, frustration and grief.
Even though Show got some "you sold out" chants last night, not all the fans joined in because they bought the storyline. Show being broke after having lost his shirt due to bad investments is believable and is something that you've heard a lot about on the news over the past 4 or 5 years. It's a simple explanation as to why he simply hasn't walked away and his "iron clad contract" is only applicable if he "perform his duties" which, in this case, seems to be doing exactly what he's told by his bosses. While there are still some holes in it, as there usually are in wrestling storylines, it still makes him sympathetic.
Like JBL alluded to, you don't always have good choices in life. You have to look at the situation and ultimately do what you think is the lesser of two evils. On one hand, Show had to do the right thing for his family. Is the "right thing" necessarily the same as the moral thing? It all depends on your perspective. Show had to hurt someone he considers a friend, someone that he's been supportive of and that he wants to see succeed. Show also has a wife and three children, who are naturally the most important people in his life. He's damned if he does and damned if he doesn't, in a no win situation where he's forced to choose between his family and personal sense of morality by a group of people who derive pleasure from his aguish. In any film or television show, this would make any character sympathetic so I don't buy into whatever bullshit double standard could be and will be applied to this situation just because it's pro wrestling.