I don't think the issue is with Chris at all. It's with what he's buying and trying to do.

There's a track record in publishing, where new money has an itch they want to scratch in old media. The last decade, this has happened in magazines and newspapers a few prominent times. Someone gets rich, they decide they want to be a publisher, and they follow their heart in regards to high quality journalism, and spout all sorts of great sounding bytes on how important x y z is.

The new money rarely realizes just how hard it is to stay afloat in the world of magazines and newspapers.

Then reality hits, and the crushing difficulty of running a magazine becomes apparent. Unfortunately, what's most likely to happen is Chris will take at least a moderate financial loss on the purchase. And he may very well not mind, that's understood.