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A Possible "Win-Win" With Holliday?

So much of how you feel about the Matt Holliday trade centers around how long you think one can reasonably hope to have him in Oakland. If you're convinced Holliday will leave as a free agent after 2009 if he's not traded sooner, then Street, Smith, and C. Gonzalez feels like a lot of 2010 strength, and "future talent" in general, to give up for a guy who will only be in Oakland while the young pitchers are emerging - but not truly emerged - onto the scene. On the other hand, if you think Holliday might be on the Opening Day roster in some season that starts with a 201_, then naturally the deal looks a lot more worth making.

Before you explain how the A's can't bid with the likes of the Yankees, how multiple big-spenders like the Yankees, Red Sox, and Angels may all be looking for an OFer next off-season, how someone will offer Holliday 6-7 years and $20-25million/year, how only a brain-dead idiot on a diet of naivete and stupid-juice could see Holliday in LF for Oakland beyond 2009, consider this possible "win-win" situation: The A's sign Holliday to an extension for 2010-11, two years, $50million.

Why it could be good for the A's:

  • The contract keeps Holliday in Oakland for two seasons in which the A's have a chance to be special. Led by more seasoned versions of Gallagher, Eveland, and Gio Gonzalez, don't be surprised if by April 2010, at least two of Cahill, Anderson, and Mazzaro have already gotten their feet wet, navigated a few bumps in the road, and settled into being solid starters who are only getting better. Feeling skeptical? I haven't even mentioned Dallas Braden, Josh Outman, and James Simmons. Add Holliday to Chavez and the current group of cost-controlled hitters (Cust, Suzuki, Sweeney, Buck, Cunningham, Barton et al) and the 2010 team is scary-good and only about to get better in 2011. That's arguably paying for two shots at the World Series.
  • $50million over two years is a heck of a lot for Oakland, but it's doable because it's a short-term commitment at a time when the A's have some payroll flexibility. Without going into the contract by contract details, after not signing Furcal or a veteran starting pitcher the A's can do it, and if you weigh the benefits of putting a highly competitve team on the field in 2010-11, you can even make a financial argument that the A's should do it.

Why it could be good for Holliday:

  • As a coveted free agent in a bad economy, Holliday can probably hope to get something like a 6 year, $140million deal, give or take a year, give or take $10million total. But if Holliday waits until 2011 to become a free agent, the economic climate is likely to be more favorable than it will be in 2009.
  • If Holliday takes his long-term contract after 2009, when he is 29 years old, after that runs out he will be in the position of looking for a shorter deal when he is about 35 years old - similar to the situation Manny Ramirez and Derek Lowe found themselves in this Winter. Will Holliday be offered better than $25million/year at that point? Likely not. So why not take a really good $25million/year deal NOW, and then a long-term deal that can take him all the way to the twilight of his career - when at 37, he can still seek a third short-term deal to end his career?

Now if you think Holliday won't get offered nearly as much when he's 31 as when he's 29, then that's a big consideration. I believe that he'll get paid more because more teams have money to spend than because he's 29 vs. 31 - at either age, for a team that can afford to pay out, Holliday is going to be a very appealing player to have for the next 6 years. I'm guessing the "bad economy" factor and "two years older" factor might roughly offset one another.

So by staying two more years with Oakland, and playing for a winning team with a positive clubhouse environment, the Math, comparatively, could look something like this:

Sign 2-year extension with A's
2010-11 (ages 30-31): $50million
2012-17 (ages 32-37): $140million
2018-19 (ages 38-39): $20million?

Take long-term contract after 2009
2010-15 (ages 30-35): $140million
2016-19 (ages 36-39): $70million?

With those figures (and I'm just guessing as best I can here), the dollar totals would come out the same - except that by staying two years with the A's, Holliday is paid more sooner, which is always good when you want your money to make money. And he gets to play for a really cool team that could be really good. And it would make me really happy. Not seeing the downside here!