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#2 Loser - Dan Gilbert
Dan Gilbert, the owner of the Cleveland Cavaliers has always had a tumultuous relationship with LeBron while he was in Cleveland. Gilbert wanted things to be done one way and James had wanted it another.
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There is a ton of speculation that they never saw eye to eye on most issues. Speculation aside, Gilbert has lost the best player in the NBA twice. They are about to drift into the lower-middle tier of the NBA and go from the national spotlight to a curiosity for Collin Sexton fans.
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