Apostrophes and quotation marks

OK, here's my sentence.

“Everything all right with the old boy?” he asked.
“Yes, DCI Searle is well,” she said, reminding him of “the old boy”’s rank.

My problem is that apostrophe next to the quotation marks. It's definitely necessary - the "old boy" possesses the rank - but so are the quotation marks, as we're reporting back the first speaker's phrase.

I tried

"the old boy's" rank

but this also looked wrong. Any thoughts?

When in doubt shuffle your sentence around. :)
I would avoid the whole apostrophe s affair, and use something like:

“Yes, DCI Searle is well,” she said, reminding him what rank “the old boy" held.

I don't think that you would put part of the phrase in quotations. I would think it would be all or nothing... either "The old man's" rank, or no quotes at all.