X-Wing DOS version...

[Muz1234]

How to change the pilot portrait for the game?

 

[FekLeyrTarg]

There's a special algorithm which chooses portraits based on the name.
This is how it works exactly:

X-wing(DOS-Collector) Portrait Asignment Algorythm Solution - XWA Upgrade

forums.xwaupgrade.com

 

[Bandit LOAF]

I remember guessing different names until I got the Mon Cal!