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1. In theory it is possible to win with one pick. In practice, it would be extremely unlikely. Given the number of people playing, someone will have a high accuracy with multiple winners and one of those players is likely to have your single homerun stock in the mix and enough other winners to beat a single pick. Keep in mind, the way TMF calculates accuracy puts more weight on a larger number of picks, so someone with 100% but only one pick isn't necessarily going to do well with the accuracy score.

2. This one's a more interesting scenario that can be gamed. Again it's possible, but highly unlikely.
It is conceivable that a late entry could take something like the TARPed Banks contest where all picks are concentrated in one sector. Because of the strong financial performance recently, the leaderboard is largely green thumb picks right now. IF the market were to turn and the financials resume their dive, someone could sneak in with an all red thumb port before the other strong red thumb player scores climb enough to go positive. In that market scenario, a last minute entry timed nearly perfectly could win. The first late starter to make a move would have to hit it perfectly. Go too late and you'll be playing catch up to someone already in the game, go too early and someone will follow you in and cover your picks. Bottom line - you need the market to set up with a well timed reversal in the sector and you need a lot of luck timing your entry.
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