There's, like, a lot of outfielders. Our 29th-ranked outfielder, Mookie Betts, isn't guaranteed a starting job. Our No. 47, Ben Revere, finished last year inside the position's top 10 fantasy performers. No. 90, Allen Craig, is an injury-plague year removed from a three-year slash line of .312/.364/.500 in 1,296 plate appearances.
Inside the top tier, we have a three-time MVP in Mike Trout (I'm through caring what the writers actually say, and yes I know that makes me sound egotistical as all hell), well-established superstars like Jose Bautista and Giancarlo Stanton, and guys who aren't even eligible at the position yet like Hanley Ramirez.
I'm going to talk about draft strategy here, and sure, there are ways to succeed and ways to fail. But with outfield, more than probably any other position, you can't really go wrong as long as you have some sense of what you're doing.
So I'll break the position's strategy into your draft placement, because a lot could change. (If you have keeper issues, or participate in an auction, this won't apply perfectly, but the lessons are the same.)
First couple picks
Congratulations! Having Mike Trout is really, really fun. (Or it should be, unless you traded him away as a rookie. *sobs*) Having Andrew McCutchen ain't too bad, either.
Here's the thing, though. Of the offensive positions, outfield is the deepest, and it isn't really close. Even if you're in an ESPN league, with five outfielders, you're more likely to find a good back-end starter there than you are a good late-round second baseman.
What that means is that, while you have your stud outfielder well in hand, you really need to ditch the position for a time. Because when it comes back around, and you can decide between Yasiel Puig or Anthony Rendon or Max Scherzer, grabbing Puig might look nice. But it means your second baseman will be Martin Prado. Or your best starter will be Jeff Samardzija. And Puig isn't worth that.
Leave outfield behind for a few rounds once you have the superduperstar. He'll carry the position while you make the rest work.
Middle of the first round
Trout and McCutchen are gone. Giancarlo Stanton probably is, too. Now you have a choice. Paul Goldschmidt or Miguel Cabrera? Felix Hernandez? Or stay with the outfield, and go Carlos Gomez or Jose Bautista?
Frankly, that's your call. Here's the thing, though: The reason, just one section above, why you could take Trout or McCutchen (or Stanton) and then relax is that those guys are so stout that they'll carry the load. The next few guys are very good, great even, but they aren't the sure things their draft predecessors are.
So take whoever you want with that middle-round pick. But you will want to jump back into the position more quickly. Take Bautista or Gomez. But, whereas Trout's second-in-command might not come around until the seventh, eighth round, or even later, the same for Gomez or Bautista will need to come sooner. Get back to the outfield earlier. George Springer (ADP 50) or Hunter Pence (53) or similar. No later.
End of the first round
Okay, so you aren't getting any of the top-top guys. But hey, end of the first, maybe Bautista is still there if you want an outfielder, or you just grab Robinson Cano or similar.
While it's true that outfield is much deeper than, say, shortstop, filling out your lineup with starters across the board before going any deeper will leave you with some subpar starters. There's a point at which it's better to just load up on outfielders, starter-named-Jimmy-Rollins-be-damned.
If I'm drafting late in the first round, I might not take an outfielder with my first pick — especially if Bautista and Gomez are gone, as there's a clear gap after them. But I'll be loading up on the position quickly. Adam Jones, Yasiel Puig, Michael Brantley, Ryan Braun, Bryce Harper. I'll get at least two of them whenever possible. Maybe three. It's not the quality of a Trout, but the quantity makes up for it.
There isn't one strategy for outfield, for the simple fact that there are so many different permutations of outfielders that you could go about it 20 different ways and find a good grouping. The main piece of advice I can offer, though, is that you don't need to overlook it.
A year ago, I was in an auction draft and kept waiting on outfield. "What's the rush?" I thought. "There are plenty of outfielders." Frankly, it worked out for my infield, and I ended up with a good one. But waiting on outfield meant I ended up with a group "headlined" by B.J. Upton, Cameron Maybin and Oscar Taveras. I finished fourth in the league, and maybe a different approach to outfield would have remedied that.
An outfielder doesn't have to be your first pick. But you also can't wait on it forever. Approach with care.