Q. I’m a book editor. The designer I work with and I seem to have been trained in different decades. We differ on whether a page number in a TOC that has chapter titles that run to multiple lines should align with the top line, or (as I think) should align on the last line of the heading. I can’t find an answer in Chicago. What say you, CMOS?
A. By default, both Microsoft Word and Adobe InDesign align page numbers on the last line of an entry that runs to more than one line in their automated tables of contents. And if your TOC includes leader dots (a row of dots that connects the last word of a chapter title or other TOC entry to the corresponding page number to its right), you shouldn’t try to alter this behavior. Ditto if the page numbers simply follow the last word in each entry (after a space) instead of being placed flush right.
But even if your TOC is formatted as a conventional table and doesn’t feature leader dots, aligning the number with the last line of a chapter title that runs to more than one line syncs with our advice for aligning rows in tables where only the first column runs to more than one line (CMOS 3.71 and fig. 3.14).
So we’d tend to side with you in this case. For a real-life example that illustrates this principle of book design, follow the Google Preview link at the University of Chicago Press’s page for Tocqueville’s Democracy in America (ed. and trans. Harvey C. Mansfield and Delba Winthrop, 2000) and scroll through that book’s lengthy table of contents.