I think I goofed. Belt pulley problem...

On my '44 H, the belt pulley was very slightly leaking from the base where the screws hold it in. So, I went to pull it apart to see what kind of gasket it needed replaced. I popped it open, caught the oil that drained out, and it stopped right where you see it. It won't pull out, and now (Here is the "opps") it won't push back in!

Questions:

1) How is this supposed to seal? The parts book only lists the 3 shims (shown) but no gasket. This is where there was oil seaping from the bottom.

2) How do I get this back together? It won't move either way.

My 2 sons & I just re-did 2 gearcases for their belt pulleys on their "H"s". M’s are similar.
Remove the capscrews under the pulley mounting flange and the shaft, spacers, & bevel gear will all slide out with a bit of assistance.
Remove the cap screw on the end of the shaft and all the parts can be pulled off.
I was able to obtain replacement bearings at no cost by going to an electric motor rebuilding shop. If my memory is correct you need a 6210 & 6208 bearing for the drive shaft. Remove any shields so the bearing will now lube itself from the transmission oil. Thoroughly clean all old grease residue before installing the used bearing. Factory bearings run $50 or so for the big one so it can be an expensive affair to replace them. NAPA wanted $45 for the 6210 size.
I have a Case/IH dealer in town (Fergus Falls, MN) so obtained the new seal, felt dust washer, and mounting gasket from them at a very reasonable cost.
Carefully clean the metal spacers and put a VERY light coating of silicone on them just before assembly. Don"t mix up the cap screws from the drive gear cover with the shaft cover; they are longer (don"t ask how I found out) and will not compress the spacers under the pulley flange.
On the drive gear shaft, just remove the 3 cap screws and pull the unit out. Remove 2 fine threaded cap screws & take the bevel gear & bearing off. It is a 6206 size. Watch out for the shift lever plunger & spring as they will jump out if the lever is moved too far. And this will happen as you clean the gear-case. If you need to replace the steel plug in the back of the gear-case, IH doesn"t have it any more. Go to an automotive parts rebuilder and get a 1 3/16" soft plug; it can be deeper (longer) than original. Put the spring & plunger back in place, set the large drive gear on the shift lever. Clean & lightly silicone the spacers and reassemble.
The 2 long bolts had copper washers but a dab of silicone will work. Be sure to put them in place in the gearcase BEFORE you slip it into place on the tractor. They won"t go in later unless you remove the gas tank or pull the gear-case back out. (I know, experience is a great teacher)
It goes without saying to carefully scrape all old gasket residue off before reassembly. Careful use of a 10" or 12" mill file will do wonders. Use it as a draw file ( sideways motion, not forward & back) to locate any high spots on the metal casting also.
I now have 2 belt pulley gear-cases that work just like new at a very minimal cost.
Sorry for the long post, I was a Vocational Engines instructor in my past life and just can"t quit teaching!!
Good luck.

Wayne, that was very thorough, but way too deep for what I want to do. What I took from that is pull the shaft out, remove the shields and clean up the bearings, put it back together and put some silicon on each of the shims at re-assembly. The silicon will keep it from seaping oil?

You got it.
Good luck.

Probably enough wear on the gears that you can delete one shim. Look closely at the contact points on the driver and driven gears for wear when you get them clean and shiny.Gordo

Wayne, I have a a leak at the pulley flange but the oil is coming out past the oil seal. I put a new seal in when I went through it but didn't take my usual cut off of the shaft to clean it up. So, all I want to do is pull the driven shaft out without disturbing the drive shaft. By your post and the parts book this seems to be possible. Correct??