I can't get the clutch brake to stop the transmission from spinning when I apply the clutch brake. The trans oil seal was torn when I took it apart the first time, so there was some gear oil in the clutch compartment but not bad. Can the clutch brake be so oil soaked that it won't apply or is the clutch not releasing. The pilot roller brg. is good. The three small springs that help release the clutch disc are good. I can see the clutch brake come in contact with the friction material too. The friction material is about 3/16 to 1/4 inch thick.
I can change gears if I'm quick shifting! This is the second time I've had the engine off to repair this problem, I thought I had it repaired the first time...

I had one D2 that the previous owner had over greased the pilot bearing and the grease was holding the clutch disc to the flywheel. When good and warm all was well but cold, the clutch brake was useless. Engaging and disengaging the clutch was problematic, specially in tight quarters. Kick the clutch out and stand on the brakes was the order of the day until everything warmed up.

I put a couple gallons of diesel in the clutch housing and proceeded to work the clutch lever, turn engine about a third of a turn, more working the clutch lever, another 1/3 turn and more on the clutch lever. After about an hour, I could hear the clutch disc finally get loose. Drained the diesel and that, as they say was that.

Thank you, yes, the pilot bearing will be changed out, even though it looks good. Cat has them$

Okay, I figured it out! I did purchase clutch brakes from Florin Tractor. They have been very helpful. But I realized that the fiber disc in the clutch was 3/4” thick, my 5J uses a 1/2” thick disc. Which are very hard to find. So I chucked my disc in my lathe and turned it down to 1/2”. Works great! The old clutch brake was oil soaked, I heated it on my shop stove, lots of nasty gear oil bubbled out, then soaked in gasoline to finish the process. So now I have a spare clutch brake set.