This may seem like a good analogy, but it's not. NYTimes owns their data; that's their intellectual property and no one would contest that. The posts on Craigslist are, if anything (see last paragraph), the property of the individual posters, not Craigslist. In fact, Craigslist makes this clear in their Terms of Use and does so largely for legal reasons: they don't want to be liable for potentially illegal posts.

Now, it's definitely a gray area to repost the individuals' content on another site, but what Eric is doing is clearly in line with the intent of the original poster: distribute a listing to get eyeballs. I'm making an assumption here, but I'm pretty sure that he would pull the post if the individual requested as much.

And finally, although I think this is a bad place to stake your claim, the posts themselves are arguably purely public data the second they hit Craigslist. The data conveyed is factual, there is no IP, and it's being disseminated publicly. It's similar to (and yes, there are a lot of ways to poke holes in this analogy, but for the sake of argument...) a town crier shouting an advertisement out in a crowded square and one of the listeners taking that information, traveling to another public square, and repeating it.