'the day I con you, Bloom, is the day I die.'
I think this line infers that Stephen did try to con Bloom, but everything went wrong when he was accidently shot by the Russian who was defending himself.
shareI think he wanted to die, guns blazing like Bloom mentioned to Penelope earlier in the film, completing the 'perfect' con where everyone gets what they wants. Bloom stays with Penelope, who is turned off being a con-artist, Diamond Dog gets his revenge, and Stephen dies. I just remembered there was a line of Stephens: 'You may not have realised it, but these cons were always about you', referring to Bloom... Thoughts?
shareYeah, I answered this somewhere else: he didn't want to be double-crossed and murdered.
He's set up the con to allow his brother to fall in love and have a "real" or "unwritten" life.
Early in the picture, though, he says, "The day I con you is the day I die."
Bloom also tells Penelope (and us) that Stephen wants to die on the con, and this con is the only one worth dying on.
Stephen doesn't want to die, but he's going to, because the con man writing the story has determined it must happen. "Everybody gets what he wants."
Although it begs the question, would Stephen want to go on conning w/o Bloom? "You are the only audience I ever needed." He finally pulls off the big card trick with, oho, the Queen of Hearts.
If Bloom finally is leaving for real, it makes sense (dramatically, within the "rules" of the story) Stephen would want to go out this way at this time.
I think Stephen wrote the entire con. He knew he was going to die. Like he said "the day I con you is the day I die." He hired DD for the con because he knew he would betray them. I think Stephen did want to die, because he didn't want to con without Bloom, and he wanted Bloom to be happy, and he knew Bloom wouldn't be happy if he was still in the picture conning and all. ie."Everybody gets what he wants." Well if Stephen wrote it, then he would die (like he wanted) Bloom and Penelope would have each other with a con free life, and DD would get the money and run. Stephen was the only one in on the con.
shareI feel like I should warn about spoilers, but I don't think that matters at this point.
However, if you saw the original ending(the last couple deleted scenes in the DVD) you'd know that originally Diamond Dog was supposed to be killed by real Russians who unwittingly bought the book from Penelope(and then later came after the brothers). Although as far as I can tell not at all mentioned, even in these deleted scenes, I think Stephen may have told the Russians about DD to cause all this, perhaps later symbolized by the card up his sleeve when he dies.
However, this is pure speculation, and furthermore isn't even technically based on the movie, as the ending was cut.