At least he hasn't gone political yet. He's got 3 superbowl wins, and a stadium that everyone calls "Jerry's World" that charges people to take a tour. It's too bad he doesn't want to build a roller coaster park, probably because there's Six Flags Over Texas right next to the stadium, and he probably thinks that is good enough.
But the thing now would be leaving behind a memory, because once he's gone, the memory of Jerry's World will fade away. In 20 years, no one will give a crap that the Cowboys won 3 Superbowls, and there's a huge stadium there, because it will be named something else, or torn down by that time. So building a huge amusement park like Dollywood would be the answer, but he doesn't care about this.