Jim O'Donnell: Next owner of the Bears -- Pat Ryan, Jeff Bezos or Neil Bluhm?
THE QUESTIONER WAS SHARP and creative.
"Which do you think will happen first?" he asked. "The Bears will be sold or the main grandstand building at Arlington Park will be imploded?"
The insouciant looked both ways before answering:
"Even money at this point in time, so put both on the board to open at 4-to-5. This one could truly go either way."
The exchange prompted later back-channel inquiries.
The most striking reply came from an individual with exceptional knowledge of the working dynamic within the McCaskey family.
That person said: "There is some internal strife going on among family members to sell ... now."
The strife makes perfect sense. Even if it is opposite to prevailing thought that the franchise will never be sold as long as Mrs. Virginia McCaskey -- age 98 -- has an earthly say.
THE HALAS/MCCASKEY CLAN IS now touching a fifth generation.
That's an expanding list of heirs waiting to hold negotiables rather than simply boast of a T-formation pedigree.
It's also outkicking the expectation. Dick Duchossois has long said: "Less than 4% of large-sized family companies make it to the fourth generation."
The entire Bears-to-Arlington Park scenario is predicated upon a nimble, resourced ownership.
Past performances suggest that isn't the McCaskeys.
They are CD sellers in a Spotified world.
Still, no one can fairly say that George McCaskey hasn't tried to carry on a noble pursuit of keeping the team in the family as a loving, dutiful son.
But is he tasked with the impossible?
IF THE SALE OF THE BEARS is announced in the weeks ahead, there are three suitors who loom larger than all others -- Pat Ryan, Jeff Bezos and Neil Bluhm.
Ryan, 83, is the favorite. The billionaire businessman -- in partnership with 91-year-old Andy McKenna -- owns 19.7% of the Bears. He also holds the right-of-first-refusal as "primary investor" if any of the McCaskey stock comes up for sale.
Sons Pat Ryan Jr. and Rob Ryan are energized entrepreneurs who have diversified interests while attempting to maintain the vigor of their father.
If Ryan were to purchase controlling interest in the Bears, one of his sons would likely emerge as an adjunct executive force to the future.
Ironically, it was Bluhm -- the billionaire who partners with Churchill Downs Inc. (CDI) in ownership of the Des Plaines/Rivers casino -- who laid the path to the Ryan-McKenna stake in the Bears.
In the winter of 1987-88, Bluhm and longtime real estate mate Judd Malkin had an agreement in place to purchase that 19.7% share from the heirs and estate of the late George "Mugs" Halas Jr., the son of "The Papa Bear."
Cash-strapped, the McCaskeys executed an eleventh-hour right-of-first-refusal to block the sale to Bluhm and Malkin for reasons of "family control."
The family turned to McKenna -- one of the consummate gentlemen in Chicago business and deal making -- to quickly plug their financial gap.
Enter Ryan with much of the $17.5 million necessary to stall the heirs of Halas Jr. They later sued, claiming the team's valuation of roughly $88 million was low. Their lawsuit failed.
(The Bears are now worth an estimated $3.5 billion.)
NO MAN IS AS WELL POSITIONED to bring the Bears to Arlington Park as Bluhm, 82.
He is the individual most responsible for steamrolling CDI on to the Illinois casino scape via its purchase of 61% of Rivers in the fall of 2018. Churchill Downs chairman Bill Carstanjen owes him.
Son Andy Bluhm, 50, has made his own mark through Delaware Street Capital. He would presumptively have a significant role in a Bears organization controlled by his father.
The inclusion of Bezos -- Amazon's $200 billion man -- is automatic on any list of NFL teams rumored to be circling the sales ring.
But it seems that the NFL wants the 57-year-old futurist more than Bezos wants the NFL.
In 2018, Dallas owner Jerry Jones chirped: "I'd carry him piggyback to get him into the NFL."
Since then, floating rumors have had assessments of four teams brought to Bezos -- the Chargers, the Seahawks, the Lions and nettlesome Washington.
Nothing has happened. So why not add the Bears?
It is all two parts information and two parts plausible dream scheming.
But the clairvoyant within can't drift into the arms of Morpheus without thinking:
There is something in the air at Halas Hall.
And it isn't all about imploding race tracks.
• Jim O'Donnell's Sports & Media column appears Thursday and Sunday. Reach him at firstname.lastname@example.org.