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I had an O'Day with a swing keel, and if they are configured the same then here is what I would suggest. Two things. First, it's a swing keel. Depending on your trailer configuration, the centerboard should swing up out of the way as you bring the boat forward onto the trailer. Having said that, if the configuration of your trailer is such that the centerboard would be damaged by this method and you can not place towels/padding over whatever the centerboard would drag over, there is method number two. Take a length of line and form a large loop. Bring the boat forward through the loop and catch your centerboard with the line. Tighten your loop and the centerboard will rise with the tightening loop. Tie it off and complete loading the boat onto the trailer. Sounds harder than it really is. Good luck. Someone once said words to the effect, "once you understand sailboats are to be worked on and not sailed upon, you will enjoy your boat more." Wise man. Enjoy, and take this opportunity to check your entire keel system for wear and tear.