Anybody ever had THIS brain fart?

So, 2-3 weeks ago, I fired Wilford the D2 up for the first time since last fall, had to run the pony for quite a while of course, but everything seemed good. Rolled him around & got the tracks mostly freed up other than one hump that really doesn't straighten out too good yet. Now, the other day I fired the pony again, & immediately got a SQUEEEEL that would send chills down your spine...I mean like a virgin sow, if you know what I mean!...:tape2:
Shut it down, checked the oil in the pony, which I already knew was OK. Fired it again, same noise...my first thought was the governor, which I know I made sure had oil before I installed the pony. Took the belt off & gov. spins nicely. Pony motor rolls over nice, not tight at all. So at that point I walked away in disgust...came back this morning after 3 days of 4-wheeler therapy, rode about 75 miles on the San Rafael Swell in Utah. But I digress...I had decided to look at the mag next, maybe a dry bushing, but the thought came to me to check the pony clutch compartment oil...dry as a Mormon wedding reception!!!
I swear I flushed it & put oil in when I got the pony back on after the rebuild but maybe not? Or else it just leaked out...Now thinking maybe the squeal is the idler gear, which is kind of high & dry? I am right in thinking it oils from the pony clutch? I don't see any other way it could get oil...
So has anybody else ever heard this noise w/a dry pony clutch, & come out smelling like a rose? (Not had to pull the pony off again?) I'm thinking maybe overfill it & roll it over to get oil way up in the gears?

I have read that it gets it's oil from the pony clutch--not much but enough to get flung around and lubricate that top gear

The gear and shaft is kind of high. The shaft has a hole to get drip oil from the gear turning. Fill it with auto transmission fluid. (flows easier). spin it over to get oil up on the gear. Stop and let it soak in between the bushing and shaft. Don't start it. Do this several times over a few days and then start it. This is what I would do. Everything may work out. Good luck.

Oil climbs all the way to crankshaft. There is a seal between crankshaft gear and front main bearing if I remember correctly, so no oil should get on the gears from the pony crankcase.

I would fill with oil and crank it over with no gas.

D2-5J's, D6-9U's, D318 and D333 power units, 12E-99E grader, 922B & 944A wheel loaders, D330C generator set, DW20 water tanker and a bunch of Jersey cows to take care of in my spare time😄

Yes, pony crankcase and pinion lube is separate (although if the crank seal gives out, then all the crank lube ends up in the pinion chamber). Level for pinion is on the front cover of the assembly.

Learned the hard way about the pony rear seal. When the pinion is leaking and has to much oil it is coming out of the pony crankcase. I check the pony oil level EVERY TIME before I start it now.

That was pretty much what I had in mind, sounds like the best plan. I did flush some diesel through this afternoon, & it came out clean, which I took as a good sign...no sparklies...maybe get time tomorrow to spin it over.