First off, to save angry emails and vague death threats, let me make clear that I am not here today to pass judgment on anyone involved in scouting or development in the A’s organization. Scouting is both an art and a science, and like keeping pitchers healthy we can see that much rides on it, many resources are devoted to it, and no one can really master it.
What I bring to the table today is more of a sense of puzzlement, knowing that some of the most obvious answers don’t entirely explain what has reached two decades of relative futility.
I get why the Astros and Cubs have infields to be envied. It’s the reward you get for enduring a series of 100-loss seasons that allow to pick from the handful of prospects everyone agrees are likely to be stars. It is no mystery why the A’s didn’t "hit on" a Kris Bryant, or a Carlos Correa, or a Bryce Harper, or any other top 3 picks that were predictably fruitful.
I also don’t begrudge that Oakland wasn’t the team that lucked into Paul Goldschmidt (8th round) or Albert Pujols (13th round), as every year there are surprises that no team saw coming. Sure, in hindsight every team would gladly have devoted their 2nd or 3rd pick to Goldschmidt but the draft is not done in hindsight.
Thing is, so many teams have drafted from worse positions than the A’s and still identified significant talent — if not one year then the next — yet Oakland’s track record lags so far behind.
How far? If you’re looking for more than just "ultimately accumulated quite a bit of WAR over his career," which might be the Cliff Pennington standard, if you’re looking for All-Star caliber players who excel both on offense and defense, the years since Oakland drafted Jason Giambi in 1992 are awfully barren.
The A’s best position player since 1992 is probably Nick Swisher, selected in the Moneyball draft of 2002. Note that this is saying, "The best position player we’ve drafted since 25 years ago is the guy we drafted 15 years ago." I will provisionally give the A’s credit for selecting Addison Russell (2012) while concurrently slamming them for foolishly trading him away. Andre Ethier also carved out a very good career, albeit exclusively with other organizations.
How much of this is the result of mediocre draft position? After all, prior to 2015 the A’s have generally either drafted low or at worst in the middle. It may be a factor, but over these years nearly every other team has drafted multiple position players who were more successful than any A’s draftee.
The Boston Red Sox, outside of one disastrous season, have been perennial AL East contenders yet have built their latest team with important contributions from the farm: Mookie Betts (5th round), Jackie Bradley Jr. (sandwich pick), joining Dustin Pedroia (2nd round). (I don’t include Andrew Benintendi because he was a 5th overall pick and the A’s have yet to pick that high.) All high draft picks, but also all picks that were made after teams passed on chances to snag them. That’s hitting on your high picks.
Oakland’s rivals across the bay have often had a better record, i.e., lower draft position, than the A’s, but recently boasted a very good infield composed almost entirely of their own draft picks: Brandon Belt (5th round), Joe Panik (29th overall pick), and Brandon Crawford (4th round). (I don’t include Buster Posey because like Benintendi, he was also a 5th overall pick following a rare down season.)
The high payroll Los Angeles Dodgers are known for buying expensive players, yet their draft has actually been essential to their success, yielding talent such as Corey Seager (18th overall pick), Cody Bellinger (4th round), and Joc Pederson (11th round).
The perennially successful Saint Louis Cardinals? Despite relatively poor draft position, they drafted such mainstays as Matt Carpenter (13th round), Stephen Piscotty (sandwich pick), Matt Adams (23rd round), and Kolten Wong (22nd overall pick).
The point being that if you take a virtual tour around the league, whether you look at playoff teams or cellar dwellers you will find a lot more than "Um...the last couple decades? Well...there was Swisher..." It’s pretty striking.
In Oakland’s defense, two truths leap out when you study the recent drafts. One is that every team has mostly drafted guys whom you’ve never heard of because they never amounted to anything -- and that includes a lot of 2nd, 3rd, 4th round picks. The other is that the A’s really do excel at drafting pitchers, from Sonny Gray to A.J. Griffin, Dan Straily and Tyson Ross, to Dallas Braden, Brett Anderson, and Trevor Cahill. Oh, and accidentally Sean Doolittle!
Yet somehow, there are position players all around the league that the A’s would love to have, all of whom were drafted by some team, none of whom were drafted by Oakland. It’s strange that the A’s haven’t even lucked into a "32nd round pick Kevin Pillar" or a "Grant Green or Mike Trout? Hmm...Let’s go with Trout."
It just makes you scratch your head a bit.