It's kind of sad, really. Person Of The Year should not necessarily be a positive thing - just the most important person of the year. But we're long since past that now.
Well, the phrasing "X of the year" is almost always taken to mean "best X of the year". Consider "movie of the year," "book of the year," and so on. Probably they should have called it "Most Influential person of the year" to avoid the default fallback of "Best person of the year".
Decades ago, Time had enough credibility that their awarding "Man of the Year" was seen as an influential act. I don't know if it was Khomeni, economics, or what, but Time has driven their brand into the ground far enough that they are now awarding it to "gosh I hope so" recipients like the pope, similar to Obama's Nobel Peace Prize.
