Try telling a user who has had a pirated application on their computer you can't provide it -- that's no fun at all. They've gotten used to using it and most won't accept another program in its place. Even worse you'll get nonsensical crap about free/open-source software not providing appropriate output.
And management isn't always helpful. You'd think telling them "you are breaking license agreements and exposing yourself to legal liability" would be enough, but sometimes that isn't enough. At least in this case you have someone (old fake IT guy) to blame -- that's more or less all you can do.
And let me chime in on the ZOMG install FOSS tip -- this is a great opportunity. You've already got a tailor-made excuse. "X user is using X software and we do not have a license. We can either pay X dollars for a license or use this freely available alternative that will provide the same functionality." In this economic climate, they won't even consider the pay software in most cases.