We'll never know about Middleton's finances but I think he's rich enough that it isn't the problem, especially as just half-owner. I don't believe for a second that he and the Bucks are pocketing profits and I'm not sure Giles ever was either (what we do know is that Giles gradually sold his stake to support himself).
If it is a real problem, Middleton would probably do the same - sell some to Comcast or bring in another partner. It better not be a real problem because I think Michael Saunders has a better chance of playing in the All-Star game than that lawsuit does of resolving quickly.
Klentak has done nothing yet. I agree with that. Could he have done more, do we know why he didn't? Yes and not really. I still expect aggression and major housecleaning over the next two years. As for this one, the drop-off from so many players has definitely been a huge bump.
But as far as the major league moves, I don't really believe he thought he was building a .500 team, I think he just wanted a slight upgrade over the likes of Cedric Hunter/David Lough, and was not confident in Altherr's health. In hindsight, he could have obviously gone with Coghlan, Nava and Altherr instead of Kendrick and Saunders. He also could have gone with scrub 6th starter type pitchers instead of Buchholtz (and even Hellickson). But the press and most fans definitely would have ripped 'em. They enjoyed the positive spring training spin and now they are getting the deserved backlash.
Would have been much better off if they'd only won 65 games last year and had set a goal of 71-75 this year. But I still don't think it is linear. The changes to the roster are going to be so drastic that what the team did this year won't have a huge relationship to what it might do next year (plus, it's still June, we should be watching a lot of new people in August too).
End of the day, Klentak is looking to the Cubs and the Astros but he and MacPhail do not bring the history Theo and Luhnow (w/ the Cardinals) did (MacPhail's was too long ago). S we'll see if he can have the same kind of success.