The 2011-2013 V6 Grand Cherokees have a Mercedes transmission that is tried and true. The 2014 models have a ZF transmission, who is generally well regarded for making some of the best transmissions in the world (with a few exceptions). The Cherokee (not GC) has a 9-speed ZF shared with other new Fiat vehicles, is one of those exceptions.
The Wranglers are also using that Mercedes transmission! I was pleased when I was shopping for my 2015 and realized that. Our 300 has the ZF 8 speed, which has been great too. In some ways, I think the 5 speed is easier to coax into the gear you want though. I'm surprised how few people consider a 300/charger when they want a large, inexpensive RWD car. They're terrific.