You can, but his example was lossy to lossy.

Right, but a his poorly constructed example might be used against his general argument that there is no way to recover the content he purchased with his hard earned money. Of course, his example of being able recover the content itself is a weak example because not everyone will have the skillset to get around DRM.

So you start with a 4MB music file with DRM and lossy compression. After stripping the DRM, you've now got a 40MB music file at the same quality. If you want to get back down to 4MB, you must lose quality.

If the source (DRM'd track) was lossy, it doesn't matter how you do it afterwards, as the quality was lost from the get go.

No shit Sherlock.

If it's lossy there's no way around it: data is already lost, wether you rip it or just listen to it.