DL 5404 then DL 5595 at JFK
Milwaukee → New York → Washington
Timetable, New York time
11:28DL 5404 from Milwaukee at the gate
10:25DL 5595 to Washington leaves the gate
22 h 57 apart on the timetable, overnight
DL 5595 leaves 22 h 57 after DL 5404 arrives on the timetable: more than half a day, so not a connection we count.