I doubt TR approval came with the thoughts of resigning him long term, it came because Tucker was a stud player with an affordable price tag for the upcoming season.
I dont feel like TR gets involved with the transactional part of the game as far as who Hoyer signs or trades he makes, I feel like he just sets the budget for the year and Hoyer does what he can to stay under it. Now at the deadline, IF Hoyer wants to add a player (s) that his remaining cost will put them over that budget, he'll need to seek approval to do so.
So, I think maybe it not TR but maybe Hoyer who may not of made that trade without feeling like he could convince Tucker to stay and TR to approve the cost to keep him.
We'll see, like you said they do have a decent shot as long as they keep winning and he enjoys being in Chicago and his teammates, anything can happen.
Question will be, will it be Hoyer or someone else making that offer for the Cubs