I was regreasing a set of tandem wheels These have Phil Woods hubs. The hubs are the first model with bearings that don't come out. I had "rebuilt" these type of hub before by removing the plastic/rubber seals (dust caps) and then picking out old grease with a dental pick, followed with new grease.
No issues with the front hub. Seals out, clean, re-greased and seals back in.

The rear hub seems to have two different sizes of seals.

The freewheel side seal popped out and that side was cleaned and the seal reinstalled.

I use a dental pick to pop out the seals. For the drum brake side the seal seemed very stiff and when I started to lift it, it immediately contorted.

I had a problem. I could have stopped but the hub needed grease. If I continued I might wreck the seal. I continued hoping I could both remove the seal and reuse it.
Unfortunately it continued to twist.

Here's Here's what the seal looks like now.



This is what an undamaged seal should look like.



The drum brake side seems to have a slightly larger size seal. I dry tested it with the freewheel side seal and it seems the axle on that side is too big for the seal to fit over.

I emailed Phil Wood and it seems they no longer carry parts for the first generation hubs. They are asking their supplier if the supplier can help but it doesn't seem likely.

So, I'm looking for a solution.

Surely someone else has had this issue. I can't simply use another seal or dust cap as Phil Woods hubs have very wide axles, wider than any other hub axle I've seen.

The alternative is to either mail the complete wheel to Phil Woods to have them replace the entire axle or strip off the hub, send just the hub to have the axle replaced and then rebuild it when the hub returns. Either way a big job and probably a big expense.