Well you can buy all the washers, which is expensive, and try them. That is what I will do next time. Use screws to bolt up the center piece nice and snug, with everything meticulously clean. Then I would just put in thicker washers until I could not spin the washer, or felt that "hint or trace of binding" Harley loves to talk about, and go back down one size.
The other possibility is to put the thinnest washer in, and try to get a feeler gauge in there to see how much thicker you can go. Or like I said, put Plastigage on thinnest washer before you bolt it up. Then you take it apart and the width of the smashed plastigage tells you how much clearance you need to take up.
Either method means when you think you have it right, do two or three rivets and make sure the washer still spins. The factory only calls for a 1 to 4 mil clearance. I will go look right now in the oldest service manual I have.
Meanwhile, if your basket has a hole drilled where the backing washer goes, then you need the pin. I assume they did not use it until later.
Against my better judgement, here is the part of the 1959-1969 service manual-- you need to find the service manual close to your bike and buy it. I think the first one was 1959 or so. The rider's handbook has some things in it, but not like the full service manual.
http://www.harleykmodel.com/literature/ ... index.html
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I can understand why you're jumping ahead to the "How do I measure it?' phase when you still need to be at the "What parts are grunged and what do I need to buy phase?" Unfortunately, I know of no way of measuring anything without both washers in there to begin with. Old Iron requires fitting, Harleys are not precision machines. Maybe buy the stock one, and the backing washer if it too is missing, and start from there.