The J-Dub Gambling Challenge 2025: The “Little Big Horn” Edition

As previously mentioned in this series, being a gambler who is also a history nerd makes for some odd comparisons. Take a trip down the Dubsism “rabbit-hole” and you’ll see a lot of weird metaphors. Anyway, a few weeks ago when the bankroll took a major hit, the analogy was made with one of history’s classic battles of annihilation.

Week 5 was another example of the horrors of gambling. But it was much worse considering I caused it through the sheer force of my own hubris. If you aren’t familiar, that’s just a more genteel wsy of saying “WHAT THE FUCK WERE YOU THINKING?”

Gentility aside, neither Napoleon or I would ever be thought of as being short on ego. But even that “Short-man Syndrome” little Corsican wasn’t so full enough of himself to put 5 Franklins on Syracuse…only to watch them lose by as many touchdowns.

It wasn’t easy finding a historical figure so hubris-forward as to seal his own fate so spectacularly. But thanks to all that history swirling in my brain, I realized I need not look across the pond for the prototypical example.  Within a single human lifetime after Europe saw Napoleon, America gave rise to Lieutenant Colonel George Armstrong Custer.  Here’s a guy whose hubris was so great his name nearly became synonymous with it. 

Many accounts have been penned as to what made Custer ignore his scouts imploring him not to take his regiment down into the Little Big Horn valley, where in the words of Bill Cosby”while every Indian in the world rides down on top of you.”

At the 1:20 mark (insert your own jokes here…)

Unlike Custer, my only aspirations are financial. The Lt. Col. believed one more decisive victory over the Indians would launch him into the White House. Either way, the two greatest hubris-launchers are power and money.  That’s why he didn’t believe his own scouts’ warning him of the ambush headed his way at Little Big Horn.  While the motivation may differ, I still took a cavalry charge of my own with complete disregard for annihilation; laying $250 on a team whose performance got its coach fired.

In either case, that’s the sort of hubris which gets your scalp separated from your skull…in the same manner the J-Dub Gambling Challenge Bankroll got skinned for $1,253. After that ambush, the season total stands at $5.028, which is still ahead of the original $5K…by a feather.

The Dubsism Legal Department…complete with extra cheese.

LEGAL DISCLAIMER (mandated by our very own Small Town Pizza Lawyer):

Thanks to the Supreme Court, gambling is no longer illegal at Bushwood, sir. However, the Supreme Court can’t really help me unless one of them is willing to keep Mrs. J-Dub from braining me with a cast-iron skillet if she found out how many dimes I’m dropping on college football.

That means that as far as she knows, all wagers are mythical in nature and this is in no way, shape, or form a gambling advice column. In other words, if you lose your own “real” money, that’s nobody’s fault but yours, so don’t yell at me when we meet at the plasma center on Monday.

If you think you have a gambling problem, go find the 800 number on your own. I’m not a goddamn public service announcement.


The Standard Plays

  • Air Force at Navy (-12) O/U 57.5 $75 Navy, $75 Under
  • Army (-7) at Alabama-Birmingham O/U 52.5 $100 Army, $100 Under
  • Clemson (-14) North Carolina O/U 47 $250 Clemson
  • Boise State at Notre Dame (-20.5) O/U 62.5 $150 Notre Dame
  • Vanderbilt at Alabama  (-10.5) O/U 53.5 $75 Vanderbilt, $75 Over
  • Syracuse at Southern Methodist (-17.5) O/U 58.5 $50 Syracuse, $50 Over
  • Penn State (-24.5) at UCLA O/U 49 $100 Over
  • Texas Tech (-9.5) at Houston O/U 51.5 $250 Texas Tech
  • Mississippi State at Texas A&M (-13.5) O/U 55.5 $100 Texas A&M
  • Texas Christian (-13.5) at Colorado  O/U 58 $250 Texas Christian, $210050 Under
  • Minnesota at Ohio State -(23.5) O/U 44.5 $100 Ohio State, $100 Over
  • Duke (-3.5) at California O/U 55.5 $50 California

The Almost Always Punitive Purdue Bet

Since I live in the heart of Big Ten country, almost literally in the shadow of Ross-Ade stadium, those around me who know I’m a gambler will invariably ask me about the Boilermakers, so I might as well bet on them…

Illinois at Purdue -(9.5) O/U 56 $50 Illinois

The Royally Ridiculous Line of the Week

Introduced by our own guest columnist King George VI (the grandfather of the current King Charles III), this feature is all about the line of the week that’s so outrageous, it’s almost as crazy as we Americans find the idea of a monarch.

Kent State at Oklahoma -(45.5) O/U 53.5 $50 Over

The Dubsism College Football Heavyweight Champ Bet:

We went back to the very first college football game in 1869, and the premise is simple…you’re the champ until somebody beats you. The current champion is the Miami (FL) Hurricanes.

Miami (FL) (-4) at Florida State O/U 53.5 $100 Miami (FL), $100 Over

J-Dub’s Payday of the Week:

It’s like the game says…the idea is to hang on to your cash. That means this is the “big play” of the week; the one that should make today “Payday.”

Iowa State at Cincinnati (-2.5) O/U 61.5 $500 Cincinnati, $500 Under


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