The Jargon File (version 4.4.7, 29 Dec 2003):

deserves to lose
 adj.

    [common] Said of someone who willfully does the Wrong Thing; humorously,
    if one uses a feature known to be marginal. What is meant is that one
    deserves the consequences of one's losing actions. ?Boy, anyone who tries
    to use mess-dos deserves to lose!? (ITS fans used to say the same
    thing of Unix; many still do.) See also screw, chomp, bagbiter.