Coulda, woulda, shoulda: The Arizona Diamondbacks hindsight draft

“The (mistakes) that really gnaw at me and I still wake up thinking about are the ones in the draft. Where you had a scout or multiple scouts in the room telling you, ‘This is the guy.’ You know, ‘We should take Chris Sale.’ We should have.”
-- Jerry DiPoto

At the time Sale was drafted in 2010, DiPoto was working for us as VP of scouting and player development. We had the sixth overall pick, but opted for Barret Loux, only to not sign him due to health concerns. At the time, there was a paranoid suspicion the team did so to roll the unsigned pick over into the (presumed, better) 2011 class - they ended up using it to get Archie Bradley. But DiPoto’s comments suggests this was more likely just a swing and a miss. Certainly, better players were left on the board, though the D-backs were not alone: 12 teams in total ended up passing on Sale, and all bar perhaps the Nats (Bryce Harper) and Orioles (Manny Machado) likely regret it.

Admittedly, given the team has finished double-digits out of first place every season since 2011, Sale probably wouldn’t have given the team any more NL West titles. However, he could have got them into the playoffs. The most convincing argument would be the 2013 season, when the Diamondbacks finished five back of the Nationals for the second NL wild-card. Sale had a 3.07 ERA for the White Sox that year and was worth 6.9 bWAR. Now, that was in the AL, so he would likely have thrown fewer innings and been a little less valuable in the NL. But even allowing for this, he might well have been the difference-maker. Who knows what might have happened thereafter...

But going back to the draft, I thought it might be interesting to see who, given the clarity only available with 20/20 hindsight, the team should have picked with their first-round choice. I’ve limited the pool of possible players to those who were actually selected in the opening five rounds. While there are sometimes gems who appear thereafter - the greatest position player and pitcher the D-backs drafted, both came in the eighth round - that’s more a case of getting lucky and catching lightning in a bottle. The first 150 or so names on the board are the players who should be scouted and known.

So, for each season, here are who the D-backs picked, and who was still available at that point. I stopped after the 2011 draft, as only a couple of players drafted subsequently (Carlos Correia and Kris Bryant) have been worth ten wins, and they were both chosen before any Arizona selection.

• 1996
  Picked: #30, Nick Bierbrodt (-1.0 career bWAR)
  Should have: #46, Jimmy Rollins (46.0)
• 1997
  Picked: #30, Jack Cust (9.3)
  Should have: #149, Michael Young (24.0)
• 1998
  Picked: #103, Darryl Conyer (N/A)
  Should have: #162, Aubrey Huff (20.2)
• 1999
  Picked: #4, Corey Myers (N/A)
  Should have: #52, Carl Crawford (38.9)
• 2000
  Picked: #69, Mike Schultz (0.0)
  Should have: #105, Cliff Lee (44.3)
  Honorable mention: #113, Yadier Molina (33.3)
• 2001
  Picked: #22, Jason Bulger (0.7)
  Should have: #49, David Wright (49.9)
• 2002
  Picked: #27, Sergio Santos (2.1)
  Should have: #44, Joey Votto (47.3)
  Honorable mention: #57, Jon Lester (40.2)
• 2003
  Picked: #19, Conor Jackson (2.3)
  Should have: #37, Adam Jones (28.6)
• 2004
  Picked: #15, Stephen Drew (17.3)
  Should have: #65, Dustin Pedroia (50.7)
• 2005
  Picked: #1, Justin Upton (26.7)
  Should have: We could have picked anyone, and J-Up is easily our best first-round position player to this date. But a whopping six players picked after Upton in the first round alone, have put up more bWAR. They are Ryan Braun (#5, 44.4), Troy Tulowitzki (#7, 43.7), Andrew McCutchen (#11, 37.5), Ryan Zimmerman (#4, 33.8) Alex Gordon (#2, 32.6) and Jacoby Ellsbury (#23, 29.1), plus outside the first round, there was Brett Gardner (#109, 30.3).
• 2006
  Picked: #11, Max Scherzer (38.0)
  Should have: We nailed this one. Not only has Scherzer been better than any subsequent player through rounds 1-5, he’s better than eight of the ten picked before him, trailing only Evan Longoria and Clayton Kershaw. Just a shame only 2.6 bWAR was for Arizona.
• 2007
  Picked: #9, Jarrod Parker (6.1)
  Should have: Jason Heyward (#14, 32.7)
  Honorable mentions: Josh Donaldson (#48, 32.5), Madison Bumgarner (#10, 29.1), Giancarlo Stanton (#76, 27.5)
• 2008
  Picked: #26, Daniel Schlereth (0.0)
  Should have: #117, Brandon Crawford (18.5)
• 2009
  Picked: #16, Bobby Borchering (N/A)
  Should have: I wonder if DiPoto still wakes up thinking about this one too, as he was also a part of the D-backs team at this point. For we opted to pass on #25, Mike Trout (48.5). Sob...
• 2010
  Picked: #6, Barret Loux (N/A)
  Should have: #13, Chris Sale (31.1)
• 2011
  Picked: #7, Archie Bradley (0.0)
  Should have: #14, Jose Fernandez (14.3). Though with true hindsight, #11 George Springer (10.8) or #8 Francisco Lindor (10.3), might be better long-term picks.

To be fair, you could likely draw up a similar list for just about every other team, and the baseball draft does have a reputation for being more random than the NFL or NBA. But picking the “best available player” just once in these 16 drafts doesn’t seem like a very good track record for the franchise. Only five, so less than one-third of our first round picks, have been worth even three WAR over their careers to date, and both Cust and Scherzer delivered their value with other teams. Hopefully, the new front-office will deliver better in this area, than previous occupants have managed.