Since the question seems to be getting ignored, I will post this again, this time with numbers to make the example of new shares being issued.
If the White Sox are a 2 billion dollar operation today, that means Jerry owning 20% makes his share of the Sox worth $400 million. Obviously you can adjust that figure to whatever he actually owns today, but I am going to use the historic 20% figure to put numbers so all of this.
So a 20% share = $400 million in value
30% = $600 million
40% = $800 million and so on.
Call each "share" 1% of the team for simplicity's sake. Jerry currently owns 20 shares out of 100. The other 80 are out there somewhere in the ether
If you issue more shares, the valuation of the company does not change. It is still the same company, with the same value and revenue, but now someone else owns a new piece, but everyone else's share gets deluded by a respective amount.
So for example, say the Sox want to raise $500 million, or approximately the worth of 25% of the team towards a stadium. There are now 125 shares, but Jerry still owns 20 shares. Those 20 shares are now only 16% of the company, instead of his former 20%. The team still is worth $2 billion, so now Jerry's shares which were worth $400 million, are now worth $320 million. The question becomes, is building a stadium going to generate enough new revenue and value that his shares go up in value more than the $80 million in equity he just gave away to get the stadium built? Say the stadium adds $500 million in valuation to the franchise, to make it worth $2.5 billion, Jerry's 16% deluded holdings are again worth $400 million. So for this to be profitable, the Sox have to add 25% in their valuation on their final selling price before Jerry dies. Again adjust the numbers to your liking, but I don't see this making a lot of sense for a guy who is 88 years old and planning his estate. Maybe if he had a decade plus to see a stadium get funded, built, and the crowds start to create revenue, but right now, that is probably a 5 year plan just getting the stadium funded and built, even if you put it on the timetable of when the lease expires in 2029.