Maybe it's a magic trick or you were turning a trick or it's a reference to Halloween or your bag of tricks or Nixon or Trichinophobia or buildign out cars. Maybe I just like to use expressions with trick in them. I guess we'll never know.
"how much tricksy must one have to hold the top spot forever?"
More than none but less than all. BTW -- you should check the Urban dictionary on "tricksy":
http://www.urbandictionary.com/define.php?term=tricksy