The last step George McCaskey should take is a page out of the Blackhawks current team president search–go outside your sport.
It is not like he needs to go far. White Sox and Bulls owner Jerry Reinsdorf, Blackhawks owner Rocky Wirtz, and Cubs owner Tom Ricketts all have championship rings this century. They may not be the most beloved by the Chicago fan base right now, and sometimes they are controversial. You cannot deny all three have more experience winning than McCaskey.
It cannot hurt to check in with those three for more than just getting sports books legalized in Illinois stadiums. Maybe he is already doing it but I doubt it.
Bulls team president Michael Reinsdorf would be a great sounding board on what steps to take to turn around a middling franchise after being a part of running it into the ground in the first place.
Also, talking with Cubs team president Jed Hoyer, White Sox team president Kenny Williams, White Sox general manager Rick Hahn, and Bulls executive vice president Artūras Karnišovas about building successful front offices and general philosophies of finding talent can go a long way. Hahn and Hoyer can even help in advising using analytics.
The key is George McCaskey needs to stop listening to Pace, Philips, and four competing owners. He needs to expand his counsel base to run a successful football organization. What he is currently doing has been complete failure.