Bill Simmons by kanyewesteros

Bill Simmons plays a game called "Guess The Lines" on his podcast with a man whose primary claim to fame is being a relative of a talk show host. Name two out three of: 1) The man's first name, 2) His relationship to the talk show host, 3) The talk show host himself

Bill Simmons's second column at ESPN in 2001 received a great deal of attention and cemented him as a rising star. In it, which (then current, now former) MLB pitcher does he argue is the Antichrist?

Bill Simmons likes to have his friends on his podcast; these frequently include a Yankee fan from Bill's youth and a Wizards fan known for prodigious feats of eating. Name these two men (only nicknames required, full names also accepted)

Bill Simmons shares an alma mater with an all-time great from his beloved Celtics. At which Patriot League school did he write for The Crusader?

Bill Simmons usually ends his mailbags with an absurd question, which he answers with a single phrase. What is this phrase?

During Bill and Jalen Rose's NBA Preview videos, Bill occasionally put on a silly hat and made predictions in character about the upcoming season. What was the name of this character?

In Bill Simmons' The Book of Basketball, he creates a pyramid of the greatest players ever. As of its original publication, name 5 of the top 6 players on his list.

Among Bill's Grantland hires was this Dartmouth graduate, who has written articles about everything from Nicki Minaj at a birthday party to an interview with Barack Obama to an explanation of Legends of the Hidden Temple. Who is this writer, who has since left for a position at New York Magazine?

Bill Simmons prides himself on correctly predicting that a certain #2 overall NBA Draft pick would have a better career than the #1 overall pick that year, but would probably like to take back the same prediction as it applies to the draft three years earlier (both drafts took place between 2000 and 2009). Which #2 pick lived up to Simmons's prediction...and which one did not? (Looking for the #2 picks, not the #1 picks)

Bill Simmons has a wife, a daughter, and a son. Name the first names of any two of them.

Bill Simmons has written two full length books: The Book of Basketball, and a previous work about his favorite baseball team. What is the title of that book?

Of which author and occasional e-mail debate partner of Bill Simmons did Simmons once marvel "Wait, I'm still reeling from the fact that you became an NBA fan just from reading back issues of Sports Illustrated in a Canadian library!" That sure would put this guy in an unusual position on the graph of NBA fans.