In my systems I have rarely if ever experienced a speaker at 1/3 the cost trumping another. However, in others' systems I have. As others have already mentioned much has to do with room placement, personal preference, room treatment application (or lack thereof) and system synergy. What's also key is the components' quality, or more specifically lack of quality. More expensive speakers in general will be more revealing, fleshing out weaknesses in gear so it may sound more fatiguing, may exhibit loose bass, etc. making the less expensive speaker preferred. Less expensive speakers commonly have "sins of omission", which may be a good thing depending on your system.
