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As for Commissioners doing really well...
They tend to know every player in the league through editing rookies or processing moves. It's a level of detail that can make a difference between getting the right backup shortstop or being left totally dry when your starter goes down for six weeks.
On last advantage they have is they never miss an export, draft, trade, free agent, etc deadline. So, there's none of those, "Crap, I forgot to send in the roster move to bring my 5 star pitcher off the DL just before the three agem series with my rival" moments.
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