This could definitely work! Imagine if every team that was sold to this conglomerate had an option to buy shares in this mega company equal to the amount that they sold their assets for? For example, on an arbitrary $5 billion deal, let's say that the value that they placed on Toronto was $500 million as opposed to $50 million for Anaheim. Maple Leaf Sports and Entertainment would buy $500 million worth of shares in this NewCo (giving them approx. 10% ownership of the league as a whole). Samueli would invest $50 million (giving him approx. 1% ownership). Profits from this NewCo would be paid out in dividends to the owners based on their percentage ownership. Thus, every team would have a financial interest in seeing their overall profitability increase.
Think about it, if Wirtz is not making smart business decisions "for the good of the league", the rest of the shareholders would be on him like crazy for his sagging division. Heck, the NewCo could even outsource to regional management firms (like Orca Bay Sports & Entertainment) and pay out corporate bonuses for financial success.
And before people start saying that this would lead to an imbalance of power where today's wealthy teams would hold the majority of shares: I have two things to add. First, right now Nashville, Carolina, et al are driving the ship (and that is not working out that great). Secondly, it would be relatively easy to have different share structures (Class A vs. Class B) with different voting rights that could easily readjust the power level to equal footing if that is what is desired.
Think about it.