In your picture you have the 1/4-20 x 3/4 screws in the wrong holes. They need to be in the threaded holes of the taper bushing. If grade 5 you can only torque to 80 in/lbs.
The threaded holes in the taper bushing is for pressing out the bushing. And really you don't even have the keyway line up in your picture which should a hint that things are not assembled correctly.
Also please post the seven digit model number as the ones coming up doesn't have this setup which is very similar to ones that Scag uses on the STT mowers.
Also if Grade 8 screws. This is per JD 652R service manual.
View attachment 68655