Largest American City Named (Directly or Indirectly) After a Roman Political Leader

Many American cities are named after American political figures (e.g., Washington, Lincoln, and Houston) after Christian religious figures (e.g., San Jose, San Diego, and San Antonio), English political figures (e.g., Baltimore and Raleigh), and other people (e.g., Columbus). But what is the largest American city named, directly or indirectly, after an ancient Roman political leader?

I also suspect that this city’s namesake is also the earliest-living person after whom a large (top 100) American city was named.

UPDATE: My suspicion in the last paragraph was mistaken, because it turns out the answer to my question is different from (and more interesting than) I first thought. Check out the comment thread for the initial answer from many people — the one I had thought of — and then what now strikes me as the correct answer from a few others. And if that is indeed the correct answer, then congratulations to Abe Delnore for being the first to spot this.