To sign, trade or let him walk: the five complicated options the Athletics have for No. 5.

Now that this appears final, what does the future hold for Matt Holliday? Better yet, where does his future lay beyond 2009?

I'm of the school of thought, with time in mind and having given up our finest positional prospect and sold low on Street, that for us to get our maximum value, we need to extend Holliday well into our Fremont years. Even with salary flexibility, that won't be easy.

First off, I'm reluctant to believe Boras will accept a pre-FA extension. For Holliday to get his max return, I think Boras will demand that he tests the market, even if we offered 6/125 tomorrow.

While I enjoy hearing that foremost on Holliday's demands is playing for a perennial contender, which I think we'll be by 2010. However, that doesn't mean Boras will allow his client to settle for a dollar short of his maximum on his biggest pay day, or that Holliday will allow that, for that matter.

Ignoring the idea that we could have kept Carlos and ponied up for Holliday a year from now, which I don't think is necessarily true, that leaves us with five options:
1) Extend Holliday before 2009, which may already be in the works.
2) Sign Furcal and/or Blake short term, show No. 5 we want to contend starting now, and perhaps sign him long term.
3) Trade him before 2009, which, if we know Billy Beane, may soon be in the works.
4) Trade him before the July deadline, which may sadly be the most likely.
5) Keep him through 2009, try to contend and let him walk, probably netting two first round picks.

I'm obviously in favor of option one, even if it requires us throw him 20 mil a year. If we expect to contend for a World Series, we haven't the offensive firepower to do so without breaking the bank for a Grade A bat. Without that bat on the way, the unfortunate reality is that the only way we can even sign a star is to trade for him first, let him be happy in the Bay Area knowing we'll be an annual contender and make him want to spend the prime of his career here. In the best case scenario, this is what happens.

Option two is really rolling the dice, both in the short and long term. Yes, A's fans might wish we would binge on more FA's and contend in 2009, but, for one, there's no saying it would work. Two, there's no saying this would keep Holliday in town beyond this year. Sure, while we could do this and also get draft picks at year's end, Holliday should be our top priority, not Rafael Furcal, Casey Blake, Giambi, Dunn or anyone else.

I look at options three and four as running in place and possibly improving to an extent. Sure, we could theoretically net a better return on Holliday than Carlos, Street & Smith. The odds of doing so, in my opinion, are better the sooner we flip Holliday to a team looking to contend that has ML-ready prospects to offer, as they'll get more bang for their buck the longer they have him. Still, save an Escobar-Kelly Johnson-type package, we're taking a similar gamble on whoever we get in return as we would have been taking on Carlos and Smith in the first place. From Beane's perspective, he'd obviously feel better with his new prospects, as he's apparently down on Carlos and the odds he reaches his ceiling.

Option five, taking draft picks, is even more of a gamble and would set our contention back even farther than if we kept Carlos and Smith. While they might not be the next Beltran and Glavine, they'd likely both have roles on the 2010-12 A's. With draft picks, we might be doing this all over again with Carlos & Smith v.2.0 3-5 years from now, if we're lucky. In other words, there's no saying with any confidence at all that the picks would turn out as well as Carlos and Smith have. If they did, it probably wouldn't be until at least 2012. That's too late.

Unless there's an angle I'm missing, I think option one - locking up Holliday ASAP - is our best option. If we're looking to contend 2010-12, it might be our only option.