Will a 1996 Dodge Durango 5.9 engine bolt to a 1999 Jeep Cherokee transmission with a 4.7 V8

Will the transmission from Dodge Durango 4×4 die4.7 motor can be replaced on 1996 grand Cherokee 5.2 4×4 ?

You would need to do some motor mount modifications, replace the PCM, replace the transmission and possibly transfer case. Its quite a process. Now if you wanted a 5.9L V8 into a 98 or older Grand Cherokee that would be a bit easier as that was an option in the 98 Grand Cherokee, so it wouldn't be too difficult of a swap into the 1st generation grand cherokee's, but due to different engine and transmission options in the 2nd generation grand cherokees 1999-2004 it would require some mechanical changes to the vehicle's engine bay. Not saying it can't be done but unless you can do the work yourself, it would be very expensive with all the custom mounts and cutting you would have to do in order to fit that engine into the vehicle