2014 Cherokee Grey Wolf 29BD and Toy Tundra V8 5.7L

If you already owned the Toyoda I would agree with the posters that say it can be done which it could with careful weight management. But since you are getting a new truck to tow with go get something that will easily do the job and make your towing experience pleasurable. For that trailer get a 3/4 ton, your choice of brand and engine. It's a little (and I mean a little) overkill but will get the job done with no problems.