Headlines and Titles of Works

Q. In the headline “Rack ’em Up and Play,” would Chicago support ’em or ’Em? (It’s for an article about a billiards-themed mobile game. We follow Chicago, so our headlines are always in title case. And we have a casual style, hence the contraction.) I’m consumed by indecision. On the one hand, ’Em is technically a pronoun, standing in for Them, and pronouns regardless of length are capitalized in headlines. On the other, I get stuck on the fact that the initial letter of the full word is what would be capitalized, and that initial letter is removed by the contraction. No initial letter, no capital? Aesthetically the lowercase option looks better to me, but other colleagues have said lowercase looks like a mistake to them. Help!

A. Our vote would be to apply an initial capital: Rack ’Em Up and Play. The similar contraction ’twas is usually written ’Twas at the beginning of a sentence (as in the opening line of that famous nineteenth-century American poem: ’Twas the night before Christmas . . .), even though the T in ’Twas would be lowercase if the contraction were to be spelled out (It was . . .). In other words, there’s at least one well-known precedent for ignoring an initial apostrophe for the purposes of capitalization.

[This answer relies on the 18th edition of CMOS (2024) unless otherwise noted.]