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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