Dewalt 995 the motor spins when pressure put on chuck

SOURCE: Dewalt Drill DC728. Chuck came out of drill body

If you find that the end of the screw inside the chuck is actually broke then you have a gear problem inside your drill. This is actually a very common problem. Sometimes people push too hard on their drills and the gears inside wear out and break. This prevent the motor from wearing out, but, the gears have to be replaced.
If it is the gears and not the chuck. you broke the minimium of the front gear or gears inside your drill. YOU CANNNOT repair gears. they need to be replaced. you may be able to find some off brand gears to work but, you run the risk that they are not as strong as your original ones, or may not be exactly grooved correctly.
so, if replacing your chuck does not work. find replacement gears. IF you cannot find the gears from the manufacturer see about replacing your drill.
If the chuck is still good, keep it. If you buy the same model, keep your old drill for replacement parts, ie, switch, armature, cord, etc.
hope this helps somewhat.

SOURCE: got a broken drill chuck i cant get off (Dewalt)

first remove the chuck retaining screw LH thread, next shift the tool to the drill only position and the low side. Find a bent handle allen wrench and insert the short piece into the chuck and clamp down, place the chuck with the long portion at about a 30 degree so you can strike it counter clockwise, usually a block of wood or work bench will do and then get a hammer and safety glasses and hit it, it might take a couple times but it will come off

SOURCE: how do you remove a key chuck from a dewalt drill

first shift the drill to the drill only position and the gear selector to the low position, remove the chuck retaining screw LH thread, find a bent handle allen wrench about the chuck capacity and lock in the jaws of the chuck, put the chuck on a block of wood at about a 30 degree angle to hit the long portion counter clockwise and strike it with a hammer, it might take a couple hits but it will come off. I misread the header last time.

SOURCE: removing the dewalt DC925 'rohm' chuck

I simply placed the chuck into a large vise and turned the drill counter clockwise and the chuck spun right off no problem without damaging anything!! It does have some thread lock on the chuck but just use your man strength and its as simple as turning the lid off the pickle jar! Do not waste your time or money with the removal tool...YOU DONT NEED IT!

SOURCE: I have a DCD940KX 18v Dewalt drill driver with the

this is not a common problem with dewalt. I have been using them in my construction business for years and only heard of this once or twice. I would go to their web site and get the number for their customer service. They stand behind their products and im sure they will help in every way they can to repair the drill