Also, some players want to be located in a big market. Chicago is the largest NFL market with a single team and is a world class city with a highly engaged fan base. There are so many teams that have bandwagon fans like Jacksonville, Atlanta, Arizona, and the LA Chargers. Chicago is a hardcore football town.
I have read this statement many times over the last 25 years.
Bulls never landed anyone significant.
Bears best signing was Julius Peppers out of how many countless failures
In the year the Sox won a title, their big FA signing was Jermaine Dye. Outside of that, the Sox have not signed a player of significance that played well.
The Cubs acquired Jon Lester which help propel them to a title. At the time, it was a significant signing. I am unsure if the above statement would apply to Lester or if he was seen in the same vein for which the statement was created. Outside of Lester, all Cub FA acquisitions have been rather underwhelming.
Most high end Free Agents bypass Chicago in all sports. The reason any Chicago franchise is successful is due to talent drafted or a trade that led to the acquisition of a impactful player.
Conclusion: Chicago will NEVER be a destination for a high end free agent and history proves that to be the case over the last quarter century.