The way this has been playing out to me is that Weiner took a picture like that at some point in his life, maybe to send to a girlfriend or something else illicit, and that picture ended up in the hands of the Loesch/Breitbart crew who crafted a narrative around it and made it happen. It definitely seems that Weiner has at least taken a picture like that before, at least from his non-denials.
I was thinking something along the same lines.
I must warn my readers that the following post is going to be highly speculative, and, for the most part, should not be taken too seriously.
For both Weiner and Wolfe, we can conceive of what I will call "innocent explanations." If it was the case that either individual was just caught up in some misunderstanding or coincidence or framing, we can imagine what they might say to explain the situation they're in:
Weiner said:
That is not me in the photo. I did not take the picture. I don't know who the individual in the photograph is, nor do I know who took the picture.
Wolfe said:
Well Andy, I was just staying up checking my twitter feed late at night, and I see Weiner has tweeted a picture to somebody. I check it out, and, as we now realize, it was a lewd picture sent to a much younger woman. I figure he must have intended to send it in private, but just got something mixed up (you know how dumb those liberals are, right Andy?) So I quickly took screenshots before he had a chance to delete it. There's really not much more to say.
(not actual quotes)
But neither of these men are saying this. In fact, they appear to be extremely reluctant to go into detail on anything. There's also that curiously specific prediction on Wolfe's part.
So I'm trying to imagine an explanation that reconciles the strange behavior of both parties. Here's what I've come up with.
Some time back (maybe months, maybe years), Weiner takes a picture of himself.
A little over two weeks ago, Wolfe acquires the photo, most likely through nefarious means.
Wolfe contacts conservative activists (possibly Breitbart) to pin it on Weiner.
The activist points out that there's nothing to go on with just the photo. It can't be tied to the congressman directly. That could be a picture of anyone.
A plan is hatched to use a yFrog exploit to make it appear as though Weiner sent the photo.
In excitement, Wolfe tips his hand about the future scandal, and posts about it on Twitter.
Two weeks later, the plan is executed.
Like I said, it's extremely speculative. I don't actually believe that the above scenario is true, because I don't have any good evidence to back it up. However, this is the only way I can really tie it all together.