After further churning this one around in my head, I think I've come up with Jimbo's possible thinking. The organization is in win-now mode, presumably because the Trib thinks a WS champion Cubs team will sell for substantially more money than the lovable losers. Whoever buys the Cubs next offseason will have to make a decision about the GM. However, if the Cubs aren't sold, the situation isn't much different. Either way, Jim knows that with his record being lackluster since 2003 and the fans starting to really turn against him, another losing season will probably cost him his job. So what does he do? He overpays for FA's to do whatever it takes to win this year. He knows that worst come to worst, Z goes to arbritration and we have him for this year. Hendry knows that if the Cubs don't win and maybe even if they do win, Z will walk, but it won't matter to him because if the Cubs lose he'd be fired regardless and if they win the WS, his job is probably safe no matter what else happens. If they make the playoffs and don't reach the WS, he's betting that the new ownership or the Trib, whichever, will come up with enough cash to satisfy Zambrano long term or that Zambrano will take a big money one year deal, to go for the WS in Chicago one last time (not a bad bet that one of these two would occur). In any case, Hendry has no reason to even care about the Cubs beyond this year. Leaving Hendry in place this offseason was, IMHO, a bad move for reasons like this. He is showing all the classic signs of a desperate GM throwing caution to the wind in a desperate play to save his own butt.