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Justin Upton TBOH Staff Pick: New York Yankees

Any contender would be happy to add the 28-year old power-hitting outfielder who will play most of the 2016 season at that age. But there are two major obstacles. First, he will be one of the most expensive free agents in baseball history, dollars-wise. Second, the cost to add him will include surrendering your top 2016 MLB Amateur Draft pick.

Another potential obstacle to his signing with some of the major contenders is his status as a corner outfielder, where a number of teams appear set. Of course one of the incumbents for such a team could possibly move in to first base, or if an AL club, the DH position could be split.