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This off season is going to be quite the ride. It's all going to come down to how accurate a read Jack has on the market, especially in relation to the other GMs. Last year, the market looked to be normal early on (recall the Ibanez contract) but pretty much collapsed late. No need to fire your bullets early if you think the targets are going to be easier to hit later.
I wouldn't write Jackson off just yet - Jack might be betting that the market is going to do nothing but get softer for him. Maybe he can get Jackson for RRS + Kelley or maybe he can get Jackson + something shiny for Morrow and Kelley. He's clearly attracted to Jackson but didn't think the early cost was worth it.
Regardless, you just can't ignore the macro market dynamics at play in trade ideas like this. There are a lot of veterans on the FA market, some teams looking to shed payroll and the pool of MLB $$ available to take on contracts is relatively shallow. Further, Detroit is in a bind and has to shed payroll. With their local market, they have no choice. Seattle is one of relatively few clubs that can easily add a $10m #2/3 starter. No need to take the first shot that presents itself.
I wonder what Detroit's internal 2010 and 2011 attendance projections look like? Pretty ugly, I'll bet. I wonder when their FSN deal is up for renegotiation...