Moneyball has been misunderstood by almost everybody, not just the condescending members of the mainstream sports media. You see, where there are undervalued assets to exploit, there are by implication overvalued ones to avoid, and while most of us can spot the usual suspects - Proven Closers©, for example - the depth of this overvaluation is so large it encompasses the heart and soul of the American baseball fan's psyche.
When a player signs an extension with the team that drafted him in lieu of chasing top dollar on the free agent market, a role model is born, a throwback to the era when fathers and sons could watch great players spend their entire careers in one city, and every time a small market team like the Rays or Padres has to give up on a Carl Crawford or Adrian Gonzalez because they can no longer afford them, the sacred fabric of baseball frays just a little.
Or something like that.
The reality is that some teams play by a different set of rules, so what I'm about to say doesn't really apply to them. What the Yankees, Red Sox, Phillies, Royals, Pirates, Marlins, and Astros all have in common, albeit for widely disparate reasons, is the simple fact that no individual player transaction is likely to make or break their playoff chances any time soon. This is not the case for the other 23 MLB franchises, for which building a 90-win team is currently both an attainable but very challenging goal.
The Minnesota Twins are a model franchise for this theory (at least they were until they moved into Target Field). As the Moneyball-Era A's faded in the early-mid 2000's, the Twins rose to contention on the strength of their scouting and player development. Of course, time doesn't stand still, and by 2007 the Twins saw Torii Hunter and Johan Santana inching towards paydays that small-market Minnesota knew it couldn't afford. Hunter was ultimately allowed to leave for free agency and Santana was traded to the Mets for a couple of marginal prospects.
Whether they realized it at the time, it was the best thing that could have happened for Minnesota.
Santana and Hunter's careers since then have played out much like the ones of dozens of others before them. With them, there's no doubt the Twins would have coasted into the 2008 postseason, rather than winning just 88 regular-season games and losing the Game 163 tiebreaker. But how would they look heading into 2012? Santana has spent all of 2011 on the DL, and Hunter is no more than the 25th-30th best corner outfielder in baseball, and together they earn $40.5 million. A richer franchise would have tried to re-sign their homegrown stars, and would have been stuck with them in 2011-2012. The Twins avoided this problem altogether, although they're now on the other side of the fence as they suffer through the first year of Joe Mauer's 8 year/$184 million extension.
Virtually every long-term contract for players past a certain age is much more likely to turn out bad than good, and keeping homegrown players around for their entire career may actually have a reverse effect on a team's playoff chances. The little-mentioned advantage that the A's, Rays, and Indians hold over teams like the Cubs and Giants is their inability to dabble in the free-agent market mostly prevents them from inflicting this damage on themselves. Being unable to sign and keep big names hurts in the short term, but by the time those players are injured, ineffective 37 year-olds still earning $20 million a season, it hurts a lot less.
Look at the Moneyball A's. They won 102 games on a shoestring budget in 2001, and then gradually let their star players walk via free agency. No doubt this hurt them in the short term, and by 2007 a low-payroll Oakland team filled mostly with no-names went 76-86. The beauty of that team was they could easily liquidate their roster and start fresh in 2008. Elsewhere, Barry Zito, Tim Hudson, Mark Mulder, Jason Isringhausen, Jason Giambi, Eric Chavez, Miguel Tejada, and Ramon Hernandez combined to put up just 10.4 total WAR that season while earning $89 million, the antithesis of flexibility. As we're currently seeing with the Cubs, it's better to lose cheaply and leave your resources free to build your next playoff contender than it is to commit them to mediocre veterans.
Sometimes, the best way to keep that money from burning a hole in your pocket is to not have it in the first place.