DL 5619 then B6 381 at Boston
Milwaukee → Boston → Richmond
Timetable, Boston time
22:02DL 5619 from Milwaukee at the gate
21:29B6 381 to Richmond leaves the gate
23 h 27 apart on the timetable, overnight
B6 381 leaves 23 h 27 after DL 5619 arrives on the timetable: more than half a day, so not a connection we count.