Never contend with a man who has nothing to lose.

The maxim advises strategic restraint: conflict is most dangerous when the other party is not deterred by loss. Someone with “nothing to lose” may take extreme risks, ignore norms, or prolong a dispute because ordinary costs—money, status, relationships, even safety—no longer restrain them. Gracián’s point is less about cowardice than about rational choice: if the downside is asymmetric, winning may still be costly, and losing could be catastrophic. The quote also implies an ethical warning—desperation can corrode judgment—so the prudent person avoids contests where escalation is likely and seeks solutions that reduce stakes rather than inflame them.