Just to throw my 1.79 cents in. You DO let the cherry win. If they are deadset against winning, you frame it as you are helping them. They are about to make a bad move, you pause the game and explain what is about to happen, (your escort is about to step into the front arc of my Imp Star II, bad idea), that kind of thing. You don't play stupid, but, don't play hard with every trick you have. And EXPLAIN every decision you make and why. That said, if the dice are not letting them win, play it off as luck, (pure and simple), and commiserate with them, (wow, look at all those blanks you rolled, holy carp).
Secondly, you run it vanilla. I taught a friend the game and we started off playing two games using the set up from the book. Using the core miniatures only and no upgrades.
Switch sides. Let them play as the rebels AND Imps. Some people only enjoy playing one side or the other, (my daughter plays most of my games and is ALWAYS Rebs. She refuses to play the "bad guys"). Well, she did play the Germans in Wings of War, but, that is because she found a "neat looking smarties plane".
Then, after you have them hooked, THEN bring in the toys, explaining each one. Help them build a list, give them some of yours, show them where to find some lists, show them some list builders, etc. The builders are a great tool because it lets them fiddle.
Lastly, once you teach someone a game, you may be their mentor for life. Be ready for that part.
Edited for the fact I am idiot and forgot to add that I know a lot of this stuff has already been said, just concurring and such
Edited by Hersh