No Power at Irrigation Pump

My irrigation pump was running fine until it tripped my breaker twice over the course of a few days.

Now it won't turn on at all.

The power is on a dedicated circuit, dual pole 20amp. It comes out of the box to a switch and then in the ground and to the pump.

I used a meter to test the voltage at the pump and it is zero. At the switch, it is a constant 240.

Is it possible to have power at the switch, but no power at the pump and have a happy breaker?

If their is a short in the ground, wouldn't the breaker stay popped?

Thanks in advance.