[[ This thread was split from the Ontario board at: http://www.chowhound.com/topics/show/... -- The Chowhound Team ]]
DDD, I'm a former Montrealer, too, and I'd like to clarify/update a couple of your points:
Ben's is no longer;
Wilenski's, while a nostalgic and interesting experience, is not a deli - it is a small lunch counter with a soda fountain, made famous in the movie, "The Apprenticeship of Duddy Kravitz", and best known for its "Wilensky's Specials", a grilled cold cut sandwich, and for its old-fashioned soda fountain drinks;
You can't talk about Montreal Jewish delis without mentioning Snowdon Deli (parent of Centre St. in Thornhill); I think it's the only one of the delis you mentioned that has chicken soup with matzo balls on the menu.
Moishe's could be considered a Jewish steak house - they have choppped liver on the menu and serve pickles and cole slaw, along with rye and pumpernickel bread.
Gibby's is not, and never was, considered a Jewish steak house, although the owner is Jewish.
For great Israeli food, there is a new place at Dufferin and Rutherford called Sofra Grill. Their falafel is amazing - crispy, light, and wonderfully seasoned, and their Israeli dips and chicken shawarma are wonderful.