It'd have to be timed very carefully. Basically, it's too early to dispatch Joe and get Heels-Up installed; her "honeymoon" phase would end long before November.
Keep drugging Joe and try to keep his poll numbers up. Then, when it gets closer to the election, Turniphead has a terrible incident. Kammie becomes the leader, and a huge funeral is arranged for the "fallen savior of democracy".
Yep, the Democrat Dream is another Wellstone funeral.