DL 5619 then DL 2586 at Boston
Milwaukee → Boston → Nashville
Timetable, Boston time
22:02DL 5619 from Milwaukee at the gate
20:15DL 2586 to Nashville leaves the gate
22 h 13 apart on the timetable, overnight
DL 2586 leaves 22 h 13 after DL 5619 arrives on the timetable: more than half a day, so not a connection we count.