Re: PIRATES ALWAYS GONNA BE A LOSER!
That's the guy's business personality. He can either make a small amount of money safely, or he can take a risk and either win big (make the playoffs) or lose big (no guarantee that a big payroll will perform).
I'd love to crunch the economics of it and see where the break-even point would be; what kind of team would we need to have to have a chance at playing in the World Series, how much would it realistically cost, and what would the return be, again realistically? I'm sure he did it and made his decision.