Charlie Doar's Biggest Nightmare
While it is highly unlikely to happen I couldn't help but imagine this scenario..
John Paxson pulls off a deal for Kobe Bryant (somehow keeping Luol Deng) and the ownerless Cubs break the bank for A-Rod (probably with false promises of Thomas McCall, remodeled Wringley locker rooms, and parades along the Milenium Mile).
Is the city of Chicago big enough to handle both sets of egoes?
Unfortunately, there's a better chance that one of the Cleveland Brown's QBs, and we're not talking Ken Dorsey, ends up in the Windy City before either of these two.
Wait, icing on the cake: Barry Bonds as the White Sox DH.