[Agrajag]

Against an AI SC it will work, but the AI doesn't really use SCs.
Humans would probably fill up their SC's slots, so it wouldn't pick up the cursed item.

Also, the strategy doesn't work as you described it.
Since the items are cursed, whatever commander finds them also gets to keep them for life (They are cursed, he can't remove them.), so its not so much the computer outfitting his SC's empty slots with cursed items, but rather that the SC is forced to equip them since he is the one that found them.
Though if you really want to, you could probably send all sorts of cursed gift items to the AI, it might not be smart enough to know better than to equip them on inappropriate commanders.
Just remember that even cursed items usually have some useful function; You might not be able to remove that Eye of Aiming, and it may just "Lost an eye" you, but it still improves precision. (Just don't equip two of them at the same time, that's counterproductive.)