To he laid by the heels; to be confined, or put in prison. Out at heels; worn, or diminished: his estate or affairs are out at heels. To turn up his heels; to turn up the knave of trumps at the game of all-fours.
♦ Having the heels of a ship; sailing faster. ...
The Sailor's Word-Book
In declining circumstances. ...
Dictionary of The Vulgar Tongue by Francis Grose