On Friday, the Cubs' new owner will be confronted by more microphones, cameras, and sweaty members of the press than I imagine he has ever been confronted by before. I predict he will say something to the effect of, "I can't give you a definite answer at this point, but that is absolutely something we are going to be looking at," more times than we'll be easily able to count. Nevertheless, after the ridiculously protracted sale process and with so many critical issues facing the team—from the immediate future of the leadership team to the long-term viability of Wrigley Field—I will join many of you in hanging on every word Ricketts has to say. (I've also never heard his voice, so I'm curious.)
Apart from all of the obvious questions Ricketts will face, probably multiple times, here are some questions I would ask if I had press credentials or the ingenuity to sneak in.
– In your wildest dreams, did you ever imagine when you began this process that it would take this long to resolve?
– How hard was it to persuade your family to pursue this purchase?
– Did you always consider yourselves favorites to win the team?
– On a scale of 1 to 10, with 1 being virtually no involvement with day-to-day decisions and 10 being complete immersion in every detail of the team's operation, how would you characterize your ideal level of involvement with the club?
– During the long period when you were clearly the eventual owner but not yet officially so, did you have any contact or decision-making authority with regard to the operation of the team? If not, were Crane Kenney or Jim Hendry at least able to "keep you in the loop"?
– Though the Ricketts family is prominent in Omaha, by the end of this press conference and the subsequent replays of it, you will not be able to go many places in Chicago without being identified. Did you or your family consider that level of visibility when deciding whether to pursue the team? How do you feel about the possibility of hostile encounters with fans if the team is not doing well?
– How often in recent years have you seen the Cubs play at Wrigley? Where did you sit?
– Dating back to when you first became a Cubs fan, who was/is your favorite player?
That's my list. What would you ask a 44-year-old billionaire-turned-baseball team-owner?
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