Here in the US, it's very difficult to prevail on a claim of either slander or libel (vis-a-vis many European countries), thanks to the First Amendment. While NYT Co may (may) be in the right regarding their first C&D, I would be shocked if they were to prevail on the second.
Very true. For libel or slander to make it to court, the plaintiff needs to show that the defendant knew his/her statement to be false. I got a hard lesson in this back in the 90s when I got sued for $2.5m.
In-house counsel is such a pain is butt. I'm dealing with John Deere's law-talkers right now and I feel for you... I'm willing to bet anyone associated with creative at the Times could give a rat's ass about your site... but the lawyers... they have to justify their existence.
It's harder in the US than many European companies, because it's not slander/libel if the information is true. However, if the information is false, than the Times could have a case.