One of the underrated benefits of the Holliday deal is the flexibility the A's now have. As I see it, there are four distinct options the A's now have. From worst case to best case scenario, they are:
1) The A's don't compete for a playoff spot, don't trade Holliday at the deadline, and don't resign him. This is by far the worst case scenario, but the A's will still definitely get two compensatory draft picks for Holliday, though it's unlikely the players they ultimately draft will be as valuable as the package they gave up to get him.
2) The A's aren't in contention in July and trade Holliday in a deadline deal. It's too far out to guess what kind of return can be had for Holliday eight months from now, but I'd say the Sabathia trade (one top A- prospect (LaPorta)) and the Harden trade (several young players with varying levels of upside (Gallagher, Patterson, Murton, Donaldson)) can be used as benchmarks. So if the A's aren't in contention and are able to deal Holliday in July, the trade still may be a net positive if they can flip him for more than the Street, Gonzalez, Smith package.
