skipper
1. noun
1
a police chief, captain or sergeant. Jocular, from the C14 nautical sense US, 1929.
2
a sport's team captain. From the use as 'a ship's captain', originally (in this sense) used of the captain of a curling team UK, 1830.
3
a mid-level boss in an organised crime enterprise US, 2003.
4
a prison warden US, 1950.
5
a railway guard US, 1946.
6
a derelict property used as shelter by the homeless. From the C16 when the original sense was 'a barn' (from Welsh ysgubor or Cornish sciber), hence 'a bed out of doors' and, finally, the current use UK, 1925.
7
in poker, a hand with five cards sequenced by twos US, 1963
2. verb
1
to live rough. From SKIPPER (a place of rest for the homeless) UK, 1845.
2
to move from house to house, staying a few nights at each, with all your worldly possessions in tow US, 1971