I've been reading a crap load of Monte Cook's articles leading up to and after the announcement of D&D 5E. It's given me some decent insight into what Monte (and by extension Wizards) sees as the essence of Old School D&D.
Before I even get to that, and before anyone starts pointing fingers at me saying I'm bashing Monte, let me just state that I think he's an excellent game designer and tinkerer of rules. The Books of Experimental Might, Phtolus, Arcana Unearthed, Dungeon a Day (well, maybe not DaD, as I found that lack luster and soon forgot to even go to the site as a subscriber) - the man knows his rules.
That being said, he has no idea what Old School gaming is about. It is not about simple stats. Okay, it is to some extent, but that just made things easier to house rule.
Greg Gillespie, author of the megadungeon Barrowmaze, put it best when he referred to the OSR as "Oh Shit! Run!" That IS the essence of Old School play. Knowing when you are outmatched and have to leave shields and valuables behind in the hopes out outrunning the nasties that will kill you and your companions otherwise. It's the thrill of outsmarting your adversaries (not necessarily outsmarting your DM, but surprising him doesnt hurt). It's thinking out of the box.
I'm kinda hooked on "Oh Shit! Run!" at the moment. Maybe if Monte looked past the rules and mechanics and actually looked at what makes Old School play different than New School, he may have a better chance at succeeding with Dungeons & Dragons 5E. If nothing else, I'll give him a +2 situational bonus to his skill roll to determine his success. DM Fiat for the win ;)
WGR1 Greyhawk Ruins (2e) By Timothy B. Brown, & Blake Mobley With The Castles & Crusades rpg - "Enter the infamous ruins of Castle Greyhawk, the most formidable and expansive dungeon on Oerth. Its mazes and catacombs have drawn hundreds of adventure...
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