Strange breaker tripping issue with A.O. Smith 1hp

It might be an issue with the main panel breakers. Sometimes breakers will go bad and trip too easily. Plus if the pump or timer was drawing too much current the sub panel should trip first since it has lower current breakers.
 
If you post the model # of your Intermatic Timer someone can tell you if it is a 120V or a 240V setup.... or you can just do a search on the Internet to find out. Failures of the 240V units are rare. I have a 35 year old timer that I had to replace the clock mechanism in a couple of times, but the contactor (switch) still works fine.
 
I have an Intermatic T20004R control panel.

I most definitely have 240v between the white and black.

I pulled the timer off and the setup is very very simple. I can see why they have such a low failure rate. What I did notice is that the copper contacts on both sides were very close in the off position. I took a flat head and made the gap a little bit wider and I'm going to see how it works now. I also found out that the lazy pool installers chose to use the light breaker itself for an on off switch rather than the $2 light switch that should have been installed. I'll make sure that gets installed before this is all back together as well.
 
Are you talking about the pool light using the breaker as the switch? Is it a GFCI breaker?

I found my pool light was not GFCI protected and I added a GFCI outlet at the pad and ran the power to the pool light off the Load side of the outlet.
 
It is not a GFCI breaker, but the load and neutral are both ran through a GFCI outlet before continuing out to the light pretty much like yours are. The wiring diagram calls for a switch to switch lights on and off but for some reason it was not installed and the breaker is labeled "lights"
 
Well, looks like my problem is fixed. The pump has been running for about 24hrs now with the timer hooked up without issue. It used to run for about 2-3 before tripping at the most. Just picked up a single pole lighted light switch to install as well.
 
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