Hyphens, En Dashes, Em Dashes

Q. Please, please help. How does one hyphenate this phrase: “twenty-five-thousand-dollar fine” or “twenty-five thousand-dollar fine”? I am not able to find an example in all of CMOS.

A. Your first version is correct. The second comes a little too close to suggesting twenty-five fines of a thousand dollars each. Please see CMOS 7.85, section 1, under “number, ordinal, + noun,” where you’ll find the examples “fifth-place contestant” and “ twenty-first-row seats.”