Question: I imported some 2000 photos into Lightroom 5 on the Mac, and then removed most of the ones in them, bringing it down to 40 photos. I did this by selecting photos I didn't like, pressing the Delete button and selecting Remove (not Delete From Disk). These removed photos are still on the filesystem, taking up 30 GB. How do I move them into the Trash on the Mac? I want to permanently delete them.

I thought Lightroom has its own trash bin, and an Empty Trash option, like iPhoto does, but it doesn't seem to.

Is there a simpler workflow to use here? I want to go through my collection, remove files I don't want, press Cmd-Z to undo a remove if I accidentally removed something and, when I'm all done, permanently delete the removed files. Is there a simpler workflow for this that I can adopt in the future? Thanks.

Answer: 
The problem is that Lightroom does not know about these images, so it cannot do anything about it. Essentially you want to know which photos are *not* in Lightroom. I have no idea how to do that but I think this will work:

From Lightroom, select the folder or tree where these photos are and synchronize it. It will popup the import dialog, just continue the import as usual. As an extra precaution add a keyword during import, something like "DELETE\_ME\_AGAIN".

Once done, all these photos *should* appear under the Previous Import folder. From there see if you can do a Delete From Disk. If not, go to the library view and do it from there by selecting all images matching the "DELETE\_ME\_AGAIN" keyword.
You needed to use the Delete From Disk option. You removed your reference to the images in Lightroom and it now has no more idea about them than it does about your Word documents and internet browsing history.

One thing you could do since you have so few images is you could make a new folder, drag the photos to keep in to that folder in the Library view (which will move the files on disk to the new folder.) After confirming they have been moved to the new folder, you can simply delete the contents of the previous folder by hand and then move the images back in Lightroom. Note that this will only work if all the files in that folder other than the ones in Lightroom should be deleted.