I think that your sheave is sized for the wire only and wont pass the 5/16" rope line. If that is the case you will need to replace the sheave. I have a phenolic one that I took off of my 1986 Catalina 27 tall rig when I replaced it with a ball bearing sheave from Catalina Direct. If you want my old one (which is not broken, split, or badly worn, I could send it to you for the price of USPS small flat rate box which is about $5.00. Andy Dalzell Catalina 27 # 6298. Sandusky Bay
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