play both sides against the middle To manipulate two opposing sides of an argument, conflict, competition, etc., against one another for one's own benefit or advantage.Similarly one may ask, what does playing both sides of the fence mean?
In a contest/argument/etc. a person is usually on one side or the other --- a member of one team or the other. But some people contrive to be members of both teams at the same time (figuratively speaking), so that whatever the outcome they will stand to gain, or benefit from the rewards.
Likewise, what does it mean to play the fence? on the fence. If you're on the fence, you can't decide something. You're torn between two options. Being on the fence means you really just can't decide. It's as if you're sitting on the fence because you can't decide which yard to play in.
Likewise, what does it mean to play both sides against the middle?
play both sides against the middle. (idiomatic) To manipulate opponents or competitors in a manner which benefits the manipulator.
What does it mean to be on both sides?
Definition of on both sides. —used to refer to the people who support a position together with the people who support the opposing positionPeople on both sides of the dispute agree that changes are necessary.
What does riding the fence mean?
From Wikipedia, the free encyclopedia. "Sitting on the fence" is a common idiom used in English to describe a person's lack of decisiveness, neutrality or hesitance to choose between two sides in an argument or a competition, or inability to decide due to lack of courage.Where does the phrase on the fence come from?
Metaphorically, sitting on the fence is straddling the position between two ideas without committing to either of them. The origin of the idiom 'on the fence' has its roots in Middle English, when the word 'fens', short for 'defens' was originated.What does off the fence mean?
This is an offshoot of the phrase “to sit on the fence”, meaning not to take any sides in a discussion or debate. “To get off the fence” therefore means to stop sitting on the fence and select a side in an argument. Let's say you and two other friends are talking about fashion. A says fashion sense is important. 
