There’s an element of chance whenever you set the starting lineup in basketball. How will so-and-so play with such-and-such? How will such-and-such matchup with this-and-that? Obviously coaches work with their players and have an intimate knowledge of their team, but that risk is there regardless; that’s why the games are played. And the margin of error gets wider the better the team.
Scott Skiles isn’t a gambler, necessarily, but he’s playing the odds and trying to put together a winning hand. Emphasis on winning (via the Orlando Sentinal):
"I’m not trying, really, to send messages," Skiles said afterward.