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I believe that in a cover 1 defense, one of the safeties will be assigned to cover Winslow - in which case I'm sure it will be Taylor, who apparently can cover like a cornerback.
If we go to a cover 2, Winslow will probably be running routes in the flat - where he'll be in the cornerback's zone, or in the middle of the field - where he'll be in the strongside linebacker's zone. In this case, the goal would probably be to keep him in front of the defense, and then hit the crap out of him when he catches the ball.
Greg Williams is an aggressive coordinator though. I'm sure they'll find a way to blitz on the strongside to the point that the Browns will start thinking about keeping him in a bit more than usual.
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