The Todd Henderson contretemps (link; cf. link, link, link, etc.) is really beginning to take on all the characteristics of a 500-car pile-up in the tule fog on Interstate Five. I doubt I can add anything directly useful at this point (and I've quit trying to read it all) but I do have one suggestion on how Todd make himself happier: increase his charitable giving. Aside from any intrinsic merit, a program of charitable giving would offer the instrumental satisfaction of taking money away from those roughnecks down at the Internal Revenue Service. It would also give him a chance to show how redistributional dollars really should be spent. And who knows, it might just possibly give him some personal satisfaction: make him feel plugged into his community, give him a generally better sense of self-worth. Tithing: yes, I recommend tithing. And none of this "Chicago Lyric Opera" or "historical society" stuff. Think Salvation Army, or Little Sisters of the Poor. A stint with a ladle at the soup kitchen might help as well.
Afterthought: In Bertrand Russell's Nightmares of Eminent People, there is a story about how Stalin dreams he dies and goes to Hell where Quakers feed him cocoa and read him tracts. Just sayin'.