This site suggests Daley is the number one gun control advocate in the country. Daley is all talk, though. I would put Bloomberg at the top of that list. As someone on the other side of the issue, I consider Bloomberg to be a lot more dangerous to our rights.
Daley is a buffoon for the most part, and has largely staked out an untenable position for much of Chicago’s gun ordinances. Bloomberg is a much stronger strategic thinker, and is better about both offense (MAIG) and defense. New York’s gun laws will be challenged, but Bloomberg will be far better about taking them back to a level where they are more defensible. That’s one reason, strategically, I think it’s wise to take on Chicago first.