Too much can happen behind you? Seriously? Do you live in some box somewhere?
Lets say we start from west point.
I'm half way to manhattan, you jump as well.
You emerge out, i'm already at fort bush trade lane, ready to jump
Then you come to that trade lane and I jump towards fort bush.
If pirates emerge behind you then you head towards me. Thats about it.
Because if a lone pirate bomber wants to blow up your transport, no ammount of escorts can save you.
Key is not to be there. Thats why a simply arrow can also scout escort