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 7.96, section 1, under “money,” where you’ll find the example “sixty-four-million-dollar question.”