Firstly, Wine project has an "application compatibility database" and it appears that Descent:Freespace has quite good ratings there - Gold or Platinum, which means your chances of making it work are not that bad: http://www.winehq.org/search?cx=partner-pub-0971840239976722%3Aw9sqbcsxtyf&cof=FORID%3A10&ie=UTF-8&q=freespace&siteurl=appdb.winehq.org%2F#1030
Secondly, when you run a command in a terminal, I bet you're getting some kind of error message there when the program crashes. Most likely you need to install some library and the error message may give you some indications of which lib is missing.
Once you have some ideas what is missing, there is a program called winetricks which helps you to install stuff (mfc runtime, directx etc.) - it installs original windows libs instead of their wine re-implementations - which may make things better or worse, you don't know until you try :)
Don't be afraid to break things - all your Wine files are stored in .wine directory so if everything stop working completely you'll be able to delete this directory and wine will reset to default settings.