Play both sides refers to taking a position in a conflict or debate that benefits you while appearing to favor one side or the other. It’s a way of manipulating a situation to your advantage. 

For example:

He was playing both sides, trying to get a better deal from either company.

The politician was accused of playing both sides of the issue, promising different things to different groups.

The company was playing both sides, offering different terms to different investors.

He had seen the coming crash, and, as any master salesman would, found a way to play both sides.

You need to play both sides: make it commercial, make it enjoyable.

Tradução: jogar dos dois lados, fazer jogo duplo.