DL 5614 then DL 5665 at Boston
Milwaukee → Boston → Richmond
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
15:20DL 5665 to Richmond leaves the gate
21 h 27 apart on the timetable, overnight
DL 5665 leaves 21 h 27 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.