swing for the fence (plural swing for the fences)
1. (baseball, softball) To hit the ball as hard as possible, with the aim of getting a home run.
Don't swing for the fence unless it's an easy ball, be content with running part way.
2. (by extension) To act in a way that might generate a very good result, but which also has a large chance of failing.
I'm not going to swing for the fence tomorrow, but I'm hoping my speech will be warmly received.
Usage notes: This is not normally used in a positive sense, mainly to caution against being overly rash.
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