What would you do?

Cant tell whats on the other side, looked like a clean blind side, and he had a spotter

 

Slide tandems fully forward to get the smallest backing radius. Close the left door to get another couple inches closer on the inside. Once he has the tandems in the hole, walk the tractor sideways by going forward and backward with steering at full lock, being mindful of the wings. Once he has enough room on the right of the tractor, swing it around and back it in. Or, politely ask the KW to drop trailer and move aside, to be safe from unintentional damage. Then there's all the room he needs.

There's a US Foods in Pittston, PA that's set up almost exactly the same.

 

That would have probably been the best thing to do. Looks like theres a crosstie wall on the right side of him? If it wasnt for that, Id have slid the tandems back and put it in there.

 

Thank god for flatbed.

 

Anybody who owns their truck would not stand by and let a stranger shimmy their trailer in like that. I'd move away.

 

Yard jockeys are a big help when you get yourself in this kind of sitch-e-a-shun!

Let your pride and ego go and ask for help. We've all been there. Drop that trailer and let the jockey handle it

 

I've seen guys trying to back in. I volunteer to drop and give an extra 20'.

 

^^^^ THAT is why I'll stick to tanks, and my occasional skateboarking in the winter months!
I've been in predicaments like that hauling vans, not fun.

 

all of the above. Saying you can't get your trailer in a hole is no sin, nor is asking for help. Done it a couple of times...."that truck ain't gonna fit in that hole......"
Not having the courtesy or decency to drop out and give another driver a brake is.