Tag Archives: Hypothetical SuperContest


Last week was fun! We got to make a video and play quarters and our picks went 3-2. Always good to have a winning week. I hope you enjoyed my video experiment; I see it as the groundwork for greater things to come. I am a multimedia gambler. Pretty soon I’ll have a gambling podcast and a gambling vlog and maybe go throwback and make a gambling xanga page. I am toying with my craft, and I am better because of it. Read More

Things got weird this week at the Hypothetical SuperContest. If you’re just here for the picks, you can find them below, but then you’ll miss the joy that is Kendrick Lamar serenading my process. I hope you enjoy our experiment.


Bears (-3) over Vikings

Buccaneers (+7.5) over Redskins

Steelers (-6) over Titans

Cardinals (-2.5) over Lions

Giants (+3.5) over 49ers

Last Week: 3-2

Overall: 21-29


Sometimes it’s hard to keep going. In the throes of what I can say with confidence is my worst gambling season since I was initiated into this fraternity of degenerates, it’s difficult to figure out why exactly I am doing this. I write a gambling column out of a love of the game and a love of the gamble, but in a season this brutal, it is challenge enough to continue loving the process, and even more challenging to write about it. My failures have not only been greater than ever before, but also more public. I am shitting my pants on stage while the spotlight is on me. Well, maybe that’s an exaggeration, but I am at the very least, publicly failing at picking football games. And that sucks.

So I look myself in the mirror and ask, with sincerity, “Why are you doing this?”

Not simply gambling, not simply writing, but living, existing, breathing. What’s the reason? Why are you here if you are just going to keep making awful picks, Tyler?

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Sorry I’m late. It was a weird week.

But gambling! Gambling on Sunday football is only three hours away! And we have games to pick! How exciting. Last week, I went 0-4 on Sunday, after entrusting my picks to some of the NFL’s heroes of facial hair. The only thing standing between me and a second 0-5 week (and probably giving up on life in general) was Colt McCoy. It was a situation I hope none of you ever find yourselves in.

But Colt came through! Washington not only covered, but actually won the game, knocking the Cowboys down a peg in those pesky Power Rankings which I despise so much. How did he do it? Read More


We’re back home.

We got off to a blazing 5-0 start in Week 1 of this Hypothetical SuperContest, but after a few down weeks and a Week 4 that I wish to never speak of again, our record against the spread was looking woeful. Last week we were able to grind out some winning favorites thanks to coin flips and confusion. Now we are back in striking distance a .500 record, and we are going to depend on the dogs to do it.

Why all the dogs you ask? Read More


If Week 1 of the Hypothetical SuperContest was a dream, Week 4 was as dark a nightmare as I could imagine.

After making it through the entirety of last season without a dreaded 0-5 week picking against the spread, my dream of avoiding imperfection forever was crushed as the Cowboys walloped the Saints on Sunday Night Football. The worst had happened. The big red buttons were pressed. Although I had started the Hypothetical Supercontest with a perfect 5-0 week, I am now in the midst of three straight losing weeks and my worst picking week since starting this column.

Something drastic had to be done. Read More


This is getting ugly.

I mean, things have been worse, but to give you an idea of how I feel about my picks recently, I google image searched “ashamed” to find this picture to lead off the column.

Last week as I attempted to bring my hypothetical picks back to hypothetical glory, I instead dug myself deeper into the pits of poor pickdom. Has my time in London finally caught up with me? Is my removal from American culture seeping through? Would I be better serving the world if I started hypothetically picking the Premiere League?


This is just a bad stretch. All gamblers go through them, and I must pass this God-given test to prove my hypothetical worthiness.

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