There are at least 3 people who I gather believe in the value of creating a "culture of winning," and they are me, Billy Beane, and Bob Melvin. However, just because these three highly qualified and esteemed baseball people -- ok fine, these two highly qualified and esteemed baseball people and some guy on the internet -- believe in a principle does not make it a principle worth valuing.
There is an oft-argued question of whether a team like the A's would be better off crashing and burning to 95-100 losses in order to grab a truly high draft pick, and perhaps the next Evan Longoria, or whether it's better to remain as competitive as possible during the rebuilding process.
One thing you have to like, right off the top, about a signing like Yoenis Cespedes is that the A's have improved now without sacrificing the future in order to do so. This is in sharp contrast to the Matt Holliday trade, where the A's either miscalculated how wide open the AL West would be in 2009, miscalculated how solid a player Carlos Gonzalez would develop to be, or quite possibly both.
That "get better now" deal set back the rebuild because it sacrificed a young player with potential; the only "downside" to the Cespedes signing is money, but in a way what the A's did is to grab a #1 draft pick without having to lose 90+ games in order to do so. So now if they were to win 75-80 games and get a lower draft pick, they would essentially be getting that lower pick plus a really high pick on top of that: Cespedes.
Not bad, but what's the point of winning 75-80 games when that won't compete for anything while you're waiting for your most talented young guys (Michael Choice, AJ Cole, Derek Norris, Sonny Gray) to move up through your minor league system, and for your most talented "major league ready" guys (Jarrod Parker, Brad Peacock, Tom Milone, Josh Reddick) to get their feet wet in the big leagues?
One point, arguably, is that if you're an 80-win team you are only 10 wins away from being a 90-win team, so much of the foundation is there and you can more easily identify targets for bridging the gap to add those "just 10 more wins". Few 65-win teams can make the jump to add 25 wins and call themselves contenders -- Tampa Bay recently being one very notable, but rare, exception -- and so you may be drafting very high but you're also needing an awful lot of chips to fall into place in order to climb the mountain from 65 wins all the way to 90. And we all know, all too well, how frequently something goes awry in the world of "talented but unproven young prospects".
Another point is that winning may require sufficiently talented players, but it is also a mindset within a team and within an organization. Students, employees, athletes -- basically, people -- have a natural tendency to rise or fall to the level of expectation, and one thing I really respect about Beane and Melvin is that I see them as being highly competitive, with the expectation that "if we're not winning a lot, then we're winning as much as we can and we're building towards winning more."
I believe that for whatever reason, Bob Geren brought a "mediocre is good enough" ethos to the team that was reflected in the team's practice habits, and subsequently its on field play. The A's didn't have the talent to win a whole lot after Melvin took over the 2010 team and perhaps more importantly the bad habits, and "culture of mediocrity," had been too entrenched in spring training, and then the first half of the season, for Melvin to reverse it significantly in June-September.
However, even though the A's most competitive years still loom in the distance, I see the Cespedes signing, even the interest in(whether you like that particular gamble or not), as efforts to keep sending an important message to the young players as they begin their A's major or minor league careers: We aren't going to sacrifice the future, like we did with the Holliday trade, but while preserving the future to be as great as possible we are going to be as good -- heck if need be, as "not bad" -- as we possibly can be, every day, every game, every season, until we're ready to go "all in" and reclaim the AL West.
I like the message this sends to the players who will have to win down the line, and I think it's the right mentality for an organization to have.