So, I've kind of wasted a day trying to crush the break cylinder back into the caliper. Been working at it for 5 hours trying every idea I come up with, is there a preferred method of doing this? Is the ABS effecting it? Kind of at a loss to describe it, it's a fairly new caliper.

 

If it's disc brakes you need a specific tool to wind them back into the caliper. Some folks use a needle nose plies or a screw driver to wind them back

 

So I went and grabbed a tool for it. When I was reassembling the wheel the rear passenger was pretty tough where as the drivers side slid right on. I think I may have bent something in all the commotion but thank you for the advice