Upright the Five of Swords is read as conflict ending in a hollow victory, defeat, or a betrayal that leaves everyone diminished; reversed, as reconciliation, letting go of a grievance, or walking away from a fight not worth finishing.
Pre-1910 cartomancy read a bare five of swords, like the suit's other fives, as a disruption of the harmony the four had settled into, discord in general rather than any specific verdict on who had won; Smith's picture is what supplies the now-standard reading that this particular conflict has a winner whose victory nonetheless costs him something, since neither the older number-based tradition nor the matching Defeat title from either the Golden Dawn or Crowley requires a winner shown smirking.
Waite's own printed meaning, degradation, destruction, revocation, and a battle that ought not to have been fought, leans harder into the ethical weight of the win than the more neutral competitive language many contemporary readers now use; the reading of this card as a caution against winning ugly, rather than simply as loss, follows Waite's text more closely than it follows the picture alone.
The two departing figures, distinct from the single winner, are frequently used by readers to represent a cost distributed across more than one party, which some practitioners take as the reason this card resists being read as purely good or purely bad news for anyone involved.