DL 5499 then WN 1582 at Detroit
Richmond → Detroit → St Louis
Timetable, Detroit time
15:05DL 5499 from Richmond at the gate
14:55WN 1582 to St Louis leaves the gate
23 h 50 apart on the timetable, overnight
WN 1582 leaves 23 h 50 after DL 5499 arrives on the timetable: more than half a day, so not a connection we count.