DL 5597 then DL 5665 at Boston
Jacksonville → Boston → Richmond
Timetable, Boston time
15:37DL 5597 from Jacksonville at the gate
15:20DL 5665 to Richmond leaves the gate
23 h 43 apart on the timetable, overnight
DL 5665 leaves 23 h 43 after DL 5597 arrives on the timetable: more than half a day, so not a connection we count.