Here is a direct answer:

I don't know what Pope Francis is or is not concerned about.

What I do know is this: Archbishop Chaput knows that the winds in the Church are now blowing towards the radical left.  Is Archbishop Chaput following the crowd?  No.  I am also sure that he knows following the crowd would certainly be more conducive to him getting a red hat--yet he does not follow the crowd.  He seems to be his own person.  The evidence suggests that he cares more about what he thinks is right than crowd pleasing and red hats. 

Cardinal Cupich on the other hand has made an about face in tone from his predecessor.  Cupich is known for being a "Pope Francis" bishop, and is a cheerleader for Pope Francis.  Cupich is radically liberal. For this he is being rewarded not only by Pope Francis but by the secular leadership in this country.  He is popular with all the liberal elites.  He has power and prestige. Appearances suggest a crowd pleaser.  

Draw your own conclusions.