how many wingmen can there be? is there a minimum distance you want between wingmen?
and the wingmen have to be anywhere on the red line?
(it would be a lot easier to evenly distribute the wingmen on a circle around the cruiser)
first I would have a variable named WingmanOffset to define how far out the box is from the cruiser.
WingmanOffset = 40 (each side of the square will be 2 x the offset)
then choose which line of the box the wingman is on (Top, Bottom, Left, Right), and pick a random point on that line.
if Top then Y = -WingmanOffset, X=random(2 x WingmanOffset) - WingmanOffset
if Bottom then Y = WingmanOffset, X=random(2 x WingmanOffset) - WingmanOffset
if Left then X = -WingmanOffset, Y=random(2 x WingmanOffset) - WingmanOffset
if Right then X = WingmanOffset, Y=random(2 x WingmanOffset) - WingmanOffset
EDIT: I should have refreshed! :) NOAH is right, the other advantage of a circle is that you can space the wingmen an equal number of degrees apart.