Being aggressive vs knowing game situation

Without being there the best play is to take it on the bounce and be aggressive on the throw (fielder has to know where he is going with it).  In that case, he might be able to prevent the runner from getting to 3B.

As always, hindsight is 20/20. 

I could see going for the catch if the runner was in scoring position (on 2B or 3B).  In that scenario, the OF has no choice but to go for it - especially if there was a runner on 3B.  If the runner is on 2B he could still play the bounce, but he'd have to come up firing for home.

I hate those situations.  I am always hesitate to tell a kid not be aggressive.  I have seen too many times that it comes back to bite you. 

So some clarification questions:

What inning?

If you'll have an opportunity to hit, who is due up?

Where to left field -- down the line or left-center gap?

Is your closer in or original pitcher? 

From that description it sounds like the left fielder didn't understand the situation.

"at what age would you expect a player to have that type of situational awareness - if ever?"

Two thoughts.

First, the scenario you described might be more about a faulty initial read (hanging liner vs. sinking liner?)  and about split-second decision-making than it is situational awareness.  The ball was lined to left.  The LF ran in. Oops, the liner is sinking.   Now he has literally a split-second....  On the other hand, perhaps LF thought "sinking liner, I'm gonna dive" from the get-go.  We don't know.

Second, to answer your question, IMO situational awareness for HS outfielders is a bonus. Not something to be expected.

A perfect example--because it's NOT under split-second time pressure-- is a catchable flyball that is lofted to the OF with less than 2 outs, and, the offense has first and third.  Throw home?  Or keep backside runner from moving up?   Unless it's really clear-cut, most HS OF's cannot be trusted to make this decision on their own.. 

It was top of the 6th, but they were running up against the time limit.  I think the batters that came up in the bottom of the inning were middle of the order.  The hit was to straightaway left.  It was a relief pitcher in.

That was my thought, but I don't really know how much thought or analysis should be expected?  We are talking HS kids, so I would expect some baseball smarts - but I don't know if I'm expecting too much? My kid is a pretty savvy player, and he hadn't really considered the totality of the situation. 

A baseball is  darned small and moves darned fast.  We think our LF is sizing up the situation in his head,   whereas what he's really thinking as he's struggling to track the ball is "Holy crap, I hope I can catch this thing."

Of course it depends on the kids experience and who has coached them.

But a USSSA major 13/14/15 yo should have this type of situational awareness.  It doesn't mean they will make the right decision or the right play, but at that age, they can think and make decisions (and mistakes) and learn from it.  It's a simple thought, "in this situation, I must keep the ball in front of me."

Agreed.  If a high school kid doesn't have this type of situational awareness he's behind the learning curve.

It's one of those situational things that you talk about but never enough.  Hard to simulate in practice and it doesn't always happen in games enough to where players are sure to learn from experience.  As Freddy alluded, left field adds an extra challenge... hardest position to get good reads on line drives. 

By the book, yes, he should have understood the situation.  In reality, not cut-and-dry easy.

So if I am reading it right, top of 6, home team in field, so his team was down by 1 run with a time limit approaching.  He makes the play, he is on Sports Center and they are hitting, down 1 and need 2.  He misses, they are down 2 and need 3.  I'm ok with the aggressive attempt. That's playing to win.     

From the time I started coaching I tried to get kids to understand they have to ask themselves, "What am I going to do if the ball is hit to me?" Even then it involves multiple scenarios and good judgement. For one player the best play might be take it on a hop and hold the runners. For another player it might be he'll have a shot at the catch but worse case scenario he blocks the ball with his body.

Some kids have better instincts and pick this stuff up at early ages. Other kids will still be trying to throw home on a single and a runner on second with two outs, up two runs in the last inning and let the hitter get to second on the throw.

My first thought in reading the OP (as ball went to the wall) was, where was he centerfielder? As Golfman mentions it may have been hit down the line- if so that was a bad risk IMO.