It appears that not all hockey articles over at Grantland are half-baked homer rants by Bill Simmons. This piece, by Kent Russell, is about the history of the Stanley Cup. It touches on the origins of the Cup in the late 1800's, many of the customs/quirks surrounding it, and one pilgrimage by a team from a prospecting town in the Yukon to challenge the juggernaut Ottawa Silver Sevens for the Cup in the early 1900's.
He Tarantinos it a little bit, jumping between the stories periodically, but I thoroughly enjoyed it and learned a bunch of things about the Stanley Cup I previously didn't know. I highly recommend giving it a read. It's a long one - like, set aside 30 minutes long - but do yourself a favor and take a look. Print it out and set it in front of the john to read in bits and pieces if you must.