In theory, you want the windlass breaker to trip before the main accessory breaker. That generally means that the main breaker would be rated higher than the windlass breaker. If you have a 40a main and a 40A windlass breaker, it's anybody's guess on which one will trip first.
But back to the issue.
Assuming things worked OK in the past and taking into consideration that now you noticed that the windlass seems sluggish, you have one of two possible problems.
The windlass motor is bad or there is now excessive voltage drop in the circuit feeding the windlass. Than also includes the negative cable wiring.
When the voltage is lower than spec'd, a motor under load will draw more current, sometimes a lot more. That can trip breakers as it should. How do we find out what is going on?
Look at connections for obvious corrosion issues.
Do a voltage test as close to the windlass as practical. We need to do three measurements. Using a known good ground as a reference( like a direct connection to the battery), measure the voltage at to the windlass. The output of the windlass breaker is a decent spot to measure the voltagefor now.
The first measurement is the standing battery voltage. Measure and make a note. (By the way, there is no way that your battery resting voltage is 14.2 volts! If you have a charger shut it off or get a new voltmeter) A decently charged lead acid battery will read maybe 12.6 volts.
OK now remove the anchor load from the windlass. That may require dropping the anchor or disconnecting it. Activate the windlass motor and measure the voltage again. It will be less than the resting voltage. Note that number.
Now put a load on the windlass. Activate it and measure the voltage while under load(hauling but not stalled). That voltage should by code be no more than 10% lower. If it is a lot lower but the small load second voltage wasn't, you have a wiring issue. If the voltage at the windlass is too low both under load and not, the windlass motor may be bad. I say 'maybe' because you can have a bad negative wiring issue and you will have the same problems.
To check the negative, first find the negative wire from the windlass where it connects at the helm probably on a buss bar and see if it is corroded.
Testing the negative circuit is different than the +12 volts. If you want to check, connect a voltmeter to the negative terminal on the battery that feeds the accessories and the other end of the voltmeter on the helm negative/ground buss bar.
Run the windlass under reasonable load and measure that voltage. It should be pretty low, and probably no more than about a half a volt. If higher, you have a problem in the negative wiring.
My tests may sound complicated but really aren't once you understand the logic.