1. Legality- Even with the 4.30 diff only goes to 16.5K tow rating.(I know it's a real buzz kill, but someone was going to say it.) 14 bales at 1600lbs is over 22,000lbs not including the trailer.
2. If your trailer does not have brakes or the brakes go out, it will take a long time to stop.
3. Pulling that much too often will put undo strain on the engine/drivetrain. Engine life will be shortened.
I had my 6.2 and trailer hauling rock when I added on to house - You weigh in - weigh out every time you leave the quarry. Total truck trailer/load max was 29,500 - The truck pulled it just fine.
I was sweating bullets - worried about trailer tires and axles.... I was on farm to market roads for 30 miles and not worries about police or traffic..
As for the question - it can be done - but if you are doing it on a regular basis you really should get a bigger rig - if you are just hauling them out of the field to headquarters each cutting - no problem -