The lowest altitude for a shuttle orbit has been 155 miles up, at a speed of 17,500 mph give or take. Even with the chuck glider thrown straight down at 100 mph, the combined speed would not bring the glider low enough to engage any meaningful atmosphere. All it would do in put the glider model into a slight different orbit that would be elliptical if launched from a circular orbit. So, from that point forward the glider would spend part of it's orbit higher than the launch platform, while other time would be lower. Both the shuttle and the glider would continue to orbit in the same plane until the shuttle deorbits.

Plenty of books on Astrodynamics, all reasonably complex.