Several years ago when I worked for the National Register of Historic Places, I had the occasion to look at the National Register nominations for Graceland (Elvis Presley's home) and the Jack Daniels Distillery. Listing on the National Register is a public process, so when a property is proposed for listing, there is a public comment period. Both Graceland and the Jack Daniels Distillery attracted numerous comments, most protesting National Register status for the buildings. Why? Well, Elvis used drugs and the distillery sold drugs (or at least alcohol) and both were undeserving for those reasons. The request for landmark status for Boston City Hall made me think of these letters, because the outright hostility to City Hall seems to stem from a fundamental misunderstanding of why landmark status is granted.
In general, landmark status is granted for historical significance, which might mean it is the birthplace of a historically important individual, the site of a significant historic event, or representative of a broader trend in history. Landmark status can also be granted for architectural significance. Architectural significance has little to do with the aesthetics of a building--architectural tastes change--but more to do with a building's importance as a representative or icon of a particular style. I would argue that Boston's City Hall has both historic and architectural significance.
My review of Thomas O' Connor's Building a New Boston gives an overview of the context in which City Hall was built and I think City Hall's importance as a representative of the "New Boston" cannot be overstated. One wonders if the Quincy Market renovation would have taken place had the Government Center renovation not preceded it. And although they came at a tremendous cost to those living in the West End and the Scollay Square areas, the new City Hall and Government Center mark the dividing line between an older, moribund, shrinking Boston and the city we know today.