Matt Holliday, acquired by the A's prior to the 2009 season, signified an egregious miscalculation by the A's brass, which was that the A's were ready to contend. Not only did the A's finish last in the ALWest that year, but they also gave up Carlos Gonzalez to get Holliday, representing a deviation from their priorities that is still aversely affecting the team today.
The 2011 Oakland A's current predicament—having a superb, young starting rotation and a marginal lineup—is, at bottom, the result from two recent erroneous team evaluations by Billy Beane and the front office.
The first occurred in 2009 when Beane, evidenced by trading for All-Star veteran and free-agent-to-be Matt Holliday, felt his team was in position to compete for the postseason. The second occurred the following year in 2010 when Beane was unable to recognize that his pitching staff was primed for success—the best in the American League (3.56 ERA), in fact—and chose not to improve a lineup littered with marginal hitters and journeymen.
An important aspect of tearing teams down and rebuilding them again is to have the foresight to gauge what stage of the rebuilding (or dismantling) process the team is at. It is not simply a matter of evaluating players and orchestrating trades. It is also about when and how it is done, and having an acute sense for when your team is over the hill and when your team is ready for contention—something Beane has a mixed track record of.
For example, Beane made an unpopular but productive trade in 2007, sending away Dan Haren for a slew of prospects that have set the A's up for what they hope will be another four- to five-year run at the postseason.
He recognized the perils of standing in no man's land—the A's finished 76-86 and 18 games out of first in 2007 with a team that wasn't going to get better—something many GMs shy away from admitting.
"We don't want to sit in the middle, going in neither direction," Beane told Susan Slusser of the San Francisco Chronicle after the Haren deal. "You have a chance to do something special or you have a chance to create something special, but to be in between is not a place we wanted to be."
In a counter example, in 2008, while just six games back of the AL West leading Angels and three-and-a-half games back of the Wild Card leading Red Sox, the A's traded their ace, Rich Harden, to the Cubs for a bunch of rejects and Josh Donaldson.
Beane cited a host of injuries to key players as reason for selling and not buying. But selling a dominant ace for peanuts while just three games back of a postseason birth with over two months in the regular season—under any circumstances—borders on sabotage.
More so than the Harden scenario, Beane's inability to recognize that the 2009 A's were at least one year away from contending has hurt the current A's team because it resulted in, as Bleacher Report's Brandon McClintock has pointed out, one of the worst trades in recent memory.
Beane undoubtedly believed that adding Matt Holliday would give them the middle-of-the-lineup guy needed to have them contend despite having a starting rotation on opening day that had a combined 63 career starts. (He also knew, however, that if they didn't, he could flip Holliday for more prospects mid-season.) This rotation featured Dallas Braden, Dana Eveland, Josh Outman and rookies Brett Anderson and Trevor Cahill, and ended the season ranked 28th in MLB in quality starts (QS).
Aside from not recognizing that neither the rotation or lineup was playoff-caliber, Beane's trade for Holliday included Huston Street and Carlos Gonzalez, who was the center piece of the Haren deal. Gonzalez is precisely the type of player the A's look to acquire—and keep—in order to build around. But Beane saw Gonzalez's inability to make consistent contact in limited playing time as a reason to jump ship on him.
This is not a hindsight analysis—it was objectively untimely, wrongfully evaluated and risky at the time. If the A's make a deal for a Holliday-type-player tomorrow, it would make much more sense because they are actually contending this year. (They finished last in the AL West in 2009.) And none of the A's prospects right now are that special or can't-miss like Gonzalez was.
Just about everyone in baseball recognized both Anderson and Gonzalez as future stars, and they were right. Beane knew Gonzalez was good, but his erroneous evaluation of the team was the premise that led to the trade.
And even though Holliday was flipped for Brett Wallace (who is already a better hitter than Daric Barton), then flipped for Michael Taylor, who has yet to do anything, the Gonzalez deal will—and should—haunt Beane for the rest of his career.
Furthermore, in 2010, with a year of experience gained by Anderson, Cahill, and Gio Gonzalez, Beane failed to recognize that addressing their impotent lineup would put them in a position to contend despite the debacle in 2009. But Beane assuredly went into the season knowing full well that he was going to let the lineup be and accept mediocrity, save money and work towards a 2011 run.
This is what makes the acquisitions of Willingham, Matsui, and Dejesus this year bittersweet: they were a year late and a buck short. The A's finished 81-81 in 2010—just nine games behind eventual AL Champion Rangers (90-72)—and addressing the lineup at that time would have put them in the same position as they are currently in this year. In short, they wasted a year of possible playoff contention.
Beane jumped the gun in 2009, hastily trading away a can't miss prospect who the A's would desperately need, and then failed to bulk up the team in 2010 when they had the best pitching staff in the AL and were ready to contend.
The A's cannot afford these kind of mistakes, yet nobody is talking about how the A's brass and its mistakes have cost them dearly. Their impotent lineup has become the over-arching narrative of the team since last year, and it is a justified reality not so much related to the A's status as a small-market team, but rather because of some poor evaluations by the A's front office that have set the team back a few years.