More than results this year, conditioning is what we should be worried about. We need to get him to sustain for 100 pitches this year, both focus and stuff.
Sure, but outside of sports how many industries exist where you lose money annually, but also keep appreciating every single year? You might be able to front run losses for a while, but eventually you'd go under.
If he has an agreement to sell, the control question is already answered. I think most people are using "sell" as a shorthand for "when Jerry no longer is the White Sox decision maker" and not drawing a deep distinction between the physical sale date of his shares vs the actual deeding of control to another person or entity.