The trouble with waiting is that the Cubs are unlikely to be out of it come July. It will be impossible from a PR perspective to deal Z in July if you're within 4 games of 1st. You deal him now, you can weather the storm of criticism if you end up contending. Call Bill Stoneman. Ask for Weaver, Kendrick and Adenhart. Call the Yankees and ask for Hughes, Sanchez + Tabata. Let them know the Angels are considering the other package. I don't think either team would bite, but if I didn't get the packages I'd simply hang on to Z and take my chances. Define "take my chances" 1. Go to arby and let him walk after 2007 or 2. Take my chances that I can get him to sign a long term near Zito deal Let me be more precise... I'd be working two separate paths at the current time. 1a) I would be working aggressively to get him signed to a hometown discount contract in the range of 5 years, $80M 1b) I would be working the phones with the teams that had a set of three premier prospects to get a trade that I was convinced improved the overall talent level of the organization If neither of those paths bore fruit, I would complete the season with Z on the staff. If, in the unlikely event that the Cubs are completely out of it in July, I'd look to trade Z. I don't think that's going to happen, though. So next October I would: 2) work aggressively to get Z signed to a hometown discount deal 3) If that didn't work, I would offer him arbitration and take the draft picks when he signs elsewhere That just about sums it up in a nutshell. that sounds good, i just dont want to end up with option 3