Some people will tell you to always crack the card out and don't just try to cross over.
I've had great personal experience crossing cards from their SGC holders, even if they are low PSA pops, if the cards look strong and worthy enough. Case in point - last month I had two 1951 Parkhurst hockey cards in SGC 96 and they both looked like solid 9's, so I crossed them while still in their SGC cases, and they both came back and crossed to PSA 9.
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