Well no thanks to all you people, I had to actually get off my couch, leave the comfort of my home and conduct my own testing.

The Droid Razr Maxx with high gloss silicone cover does NOT fit in into the Maxx Navigation Dock that they sell in Verizon. But I bought the Navigation Vehicle Dock from Best Buy for the regular Droid Razr (red and white box 89525N) and the Razr Maxx with silicone cover will fit in that after removing the insert. You just have to push in the USB side of the phone and insert the usb plug first before pushing in the other side. And this dock is a much better deal since for the same $40 they also throw in the rapid vehicle charger and the combo audio/USB cable.