The cotter pin is really only there to keep the weep hole from getting plugged up with dirt/mud etc. It is meant to rotate when driving through long grass etc. The purpose of the hole is to allow any fluid that does leak a way out so as not to get the clutch (and starter in my case) full of gear oil. If you have a small leak from there I am told this is normal. Anything more than a few drops and I'd say you might want to consider further investigation.
Now, without you saying what model your tractor is, I can't say for sure that the next piece of information will be valid. From what I know of my TO35 it's possible that you may be able to remove the inspection plate and fit a new cotter pin in the weep hole from inside, without having to split.
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Today's Featured Article - Identifying Tractor Noises - by Curtis Von Fange. Listening To Your Tractor : Part 3 - In this series we are continuing to learn the fine art of listening to our tractor in hopes of keeping it running longer. One particularly important facet is to hear and identify the particular noises that our
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