Based on the "Boy Scout" line, I assume Kirk met David a few times. I wonder what Kirk did to make David recall him as a Boy Scout?
I always took the comment as sarcastic criticism of Kirk/Starfleet. The Boy Scout reference plays on the aspect of a uniformed service while simultaneously referring to Starfleet as children pretending to be in a uniformed government agency.
I don't think David ever met Kirk or, if he did, it was briefly. David only had stories or, possibly, recorded documentation about Kirk to form an opinion from.