2009...Meh...
This team is heading nowhere quick. The Jays need to rebuild.
I'd trade Halladay and Wells and Ryan. Restock. Start again. They don't have the money to just add parts and compete with the Sox and the Yankees in 2009. The Yanks will add CC, Burnett, maybe Tex. We can't even afford one of those guys, and adding another questionable arm won't put us over the top. Next year will be a down year as we wait for Marcum and McGowan to come back. You are not going to win anything with Litsch as your #2 starter.
Halladay is great, I know, but his value will never be higher (and he can't propel us into the playoffs on his own). McGowan may be ready by May 1st, but who knows, and Litsch may improve, but he should never be more than a #4 starter.
I'd keep the young guys in the OF and flip the vets. Maybe start another 5 year plan. Adding Ecksteins and Menches and Wilkersons just won't cut it when Boston is adding Lowes and NY is adding Burnetts and Sabathias. We need to go uber-young, like Tampa. The Wells/Halladay window may be closed I fear.