Yes, the money for Joan came out of the magic bean rainy day fund that John Henry doesn't care about, but other investments are made more rationally.
I mean, that seems like the most straightforward explanation to me.
Whether you consider something an annuity or pay for it once, there is an NPV. John Henry understands this and trusted his baseball folks to make the right decisions. I can't believe how many people (even at the time of signing) don't understand that that 100%(!!!!) penalty actually makes it harder to break even than you would with going over the luxo tax. And that's fine. What do I care, really, other than I can't take reading these same arguments that only certain money counts. It all comes from somewhere, it all fucking counts. The calculations of the true cost and the expected returns and everything else can be subject to different variables, but there is no denying that the money has to come from somewhere, and presumably all money put toward talent acquisition for the Boston Red Sox comes from essentially the same place.
Let me put it this way, say you are in the market for a new car. It costs $50K, but you can finance it for 10% down and 0% interest for 5 years ($750/month). Is the latter deal "worse" because there is ongoing cost? In fact, if you have any way to invest the money, the latter deal is better, all things being equal. Now, you can say "but if I finance I have to insure extra to meet the bank's requirements and that costs me an extra $50/month" or whatever. OK, now you can start doing a calculation of which method pays you back and how much risk you are willing to take on, etc. But at the end of the day, your money is still being spent, either way.