Ridiculous Holiday Mailbag

If you are a sports fan and you don’t read Bill Simmons by now, you should really get on that… or if you’re too lazy to listen, get his podcast. He recently put out his ridiculous holiday mailbag email because as he stated that someone could justify that “Maybe I needed something to distract me from the terrifying realization that the Patriots’ 2008 season rests in the hands of Brett Favre”. Well said.

I’ll quote a couple of the completely bizarre emails that were sent to him with his replies and you can read the rest of them here: Sublime meets ridiculous in holiday mailbag


Q: How ’bout this hypothetical? It’s 2012, Matt Cassel is the quarterback for the Vikings and standing with a Super Bowl MVP trophy in one hand and a Super Bowl trophy in another. It’s his third Super Bowl MVP in four years, two with the Vikings and one with the Patriots in 2009. He states in his opening remarks, “I would like to dedicate this Super Bowl to Tom Brady for getting injured and allowing me to finally get my shot.” Flash to Foxboro, where Tom Brady has never returned to his 2007 form and reinjured his knee three times since, and Bill Belichick has retired from coaching due to having a heart attack from seeing Cassel win his second Super Bowl without the Patriots. Jump to 2022, as the Patriots have become the ’90s Cincinnati Bengals and you are hysterically crying while writing a piece titled “The Curse of Matt Cassel: IT IS REAL.”
— Andrew, Boston

SG: Just real enough that I made the same face that babies make when you stick a lemon in their mouths.


Q: If you’re sitting on 24 wins in “Streak for the Cash,” shouldn’t you hop on a flight to Vegas and bet about $250,000 on the opposite of whatever you pick for your 25th selection? All the games ESPN.com puts up as straight win/loss picks are close in point spreads, so I am sure you could get a money line in Vegas that would pay out straight up. That way, you ensure yourself of a minimum victory of $250,000, and can win a maximum of $750,000. I mean, you gotta protect yourself at this point right? I’m sitting in class at law school going insane thinking about this guy NOT doing this.
— Bryan, New York

SG: One catch: Where do you get the $250,000 to slap down at a sports book? This plan only works if you’re a multimillionaire or you’re running a Ponzi scheme. By the way, you’re not gonna believe this, but Bill Simmons is a huge “Streak For the Cash” fan. Every time I get to three in a row, I start dreaming about ESPN.com’s worst-case scenario of one of its employees (in this case, me) beating the game, followed by a mammoth Bob Ley investigation and 27 caustic Phil Mushnick columns.


Q: When I found out Al Davis’ mother lived until she was 103, I thought about impaling myself with a dull garden tool about 103 times. I’ll be 67 by the time the Raiders are respectable again. Can you please offer me some hope?
— Scott, Holiday, Fla.

SG: (Shaking my head sadly.)



Q: I don’t care what the SEC says: The J-Kidd transaction was Cuban’s greatest trading transgression of 2008.
— Marchy, Malibu, Calif.

SG: (Applauding.)