How do I apply a drop cap when the sentence starts in quotes?

You mean something like this

Ingenious, indeed.

The GREP style is applied automatically; only thing is you have to remember to manually set the number of characters for the Drop Cap to 2. Perhaps it's safest to create a separate paragraph style for this.

Oh yes I forgot to include the other dialog screenshots – I hoped it was obvious. But wanted to clarify the end result before elaborating :)

you also need to have a baseline shift and other things too. Be cool to see how others would tackle this too :)

Eugene, I think you're focusing on the formatting of the quote, rather than the original question, which is simpler: How to make both the quote mark and the first letter drop.

@pik80: Fortunately, you can set the number of characters to drop to 2. You'd probably want to do this in the Drop Caps & Nested Styles pane of the paragraph styles dialog box, but you could also do it manually in the Control panel.

In fact, if you subscribe to InDesign Magazine, you'll find an article about drop caps by the wonderful Nigel French in the issue coming out next week! He describes this very situation.

David, to me it seems like they only want the first letter of the quote to be a drop cap, and not the actual quotation mark… perhaps I have read it wrongly?

'Tis a bit ambiguous, Eugene. Meself, I'd be using a 2-character drop cap setting and turning on “Optical Margins” with a 'normous point size setting. After a few pints you'd never know the difference… :-)

According to the Chicago Manual of Style, the open quote is often dropped when the design calls for a drop cap, and I think that this is by far the most attractive solution. CMS goes on to say that if the open quote is retained, it should appear at the same size and vertical alignment as the normal text, not be part of the larger drop cap style.

I currently use paragraph styles to add drop caps and nested styles, and while nested styles allows you to apply it through 1 letter, drop caps only allows you to apply it through characters or lines. When we have an initial quote, I want (usually) to hide the initial quote from the print version in InDesign and make the first letter a drop cap. I have figured out how to do this for stick-up caps with nested styles, but cannot find the appropriate workaround for using a drop cap, nor can I find a way of styling the drop cap without using that feature in the paragraph style. Below is the instructions I have thus far: do you know of a way to get drop caps through 1 letter instead of through 1 or 2 characters?
1) In all paragraph styles you want to have no initial quote, go to the GREP Styles. In the To Text field, type ^” (which says find quote mark at beginning of paragraph).
2) Make Apply Style hidden_character (or something to that effect), and style that Character Style as 0.1 pt (in Basic Character Formats), Horizontal Scale 10% (in Advanced Character Formats), Color: [None] (in Character Color).
3) Apply any character style you want to “through 1 Letters” in Nested Styles. The Drop Cap option in Paragraph Styles will NOT work, as Drop Caps allow you to apply to Lines and Characters, but not Through 1 Letter. (If you do Characters in Drop Caps, you would need 1 for most paragraphs, and 2 for any paragraphs with the initial quote.)

I like the grep styles trick.
But if you want to make the quote disappear in the print version, but not in other versions, then I would suggest applying Conditional Text to it instead, and then turning that condition on/off, depending on output.

Thank you! I had not worked with Conditional Text, so that worked, except for the fact that I forgot to mention that my content is Locked: it comes in in InCopy and I don’t want to Check it Out if I don’t have to. I may be able to get this coded in to the InCopy file, but is there a way to label that Conditional Text as a subset of a Paragraph Style? Otherwise I will have to Check it Out and find each instance myself.

So I looked into this some more: Conditional Text cannot be worked with in InCopy, and I can’t find a way to get Character Styles to link to Conditional Text. In order to not check out the files, I thought I could just make a character style conditional text, and embed the character style nested in a paragraph style, but apparently those two don’t link. Am I missing something, or is there really no way to call a Character Style to use the Conditional Text feature?