Somehow this bothered me ever since season 3 when Jack reads the obit about someone dying in NY.

Who would have transported him to LA?

I think the obit just said the person was from NY. I don't think it said he died in NY. I could be wrong though... :)

Still, wasn't the passport Widmore gave him from Canada? Was he supposedly a Canadian living in New York City?

The article is about a man from New York who was found dead in Los Angeles.

http://lostpedia.wikia.com/wiki/Newspaper_clipping

i was gonna say. he visited kate and jack last and they're both in LA.