I tried that on another older Chtomebook that I am not using and it didn't work for me.
It didn't give me two smaller ones to delete.
No pop up that said delete.

The only way I could get it off that Chromebook was a powerwash. But as soon as you download something again it was back.

The reason I hate it is .. I hate the tote pinned files. Clearing history doesn't get them out of your Chromebook. You have to delete a million of them one at a time.

When I am making a animated gif or a mp4 I have tons of downloads to delete every day.