You need to look up the story on The Denver fiasco
The McDaniels/Cutler feud was well documented and the team wasn't giving him that loving feeling, but how many times has a QB just outright forced the team to trade him? These type of disagreements happen often, but it's rare for a player to take a hard stance. Now that the Cutler chapter has closed we have 20/20 hindsight and realize he's just a dick. I'm not saying he's a horrible person, but rather Jay is going to be Jay and if asked to change he'd rather move on. Very rare stance for a team's president/CEO/QB (all those roles do combine because the QB defaults to being the face of the franchise).
Look at Aaron Rodgers in GB. He's also a dick and there are rumors that him and McCarthy never got along. How did that play out? They worked together for 11 seasons, won one Superbowl and eventually McCarthy got canned. Did Rodgers, who again, is a dick, ever force his way out? No. There might have been discussions, but it never happened.
Anyway, to my point - It's pretty rare for a player to force their way out. They have to be very calculated in knowing their market value, what teams will be willing to trade and that when forced the current team will be willing to listen. In this situation I'd say Robbie has grossly overestimated his leverage. He should take a lesson from Kirk Cousins and just sign the franchise tag, get paid ~$4.9M (making him the second highest paid kicker in the league) and hit free agency next year.
If his heart is truly in Chicago (or somewhere else) he has to wait a season to let that happen.