This is an ongoing blog series that features gambling stories from you guys.
A true double whammy.
Maybe not the most salacious degeneracy, but we got some good stuff here guys.

Let’s get into it:
Baseball Coach.
I have been gambling my whole life on horses and sports.
10 years ago I was fortunate enough to start my own business while also being a college baseball coach.

I did my research on the pay per head sites and decided to open up my own.
Now at the same time that I was coaching I was also operating the business.
It was a perfect feeder system for my business.
They also seemed to gamble a bit too.
- wink wink it was me…shhhhh*
Sure enough they all switched over.
Only 2 weeks in the past 5 years have I actually had to pay the full payroll!
Am I an asshole for taking their wage before it even hits their hands?
This is the small business American dream on steroids.
Amateur athletes funneling wages back to the business owner on bad bets is outstanding.
Makes me think there should be a pre-tax gambling benefit authorized by congress.
Like a Health Savings Account but linked to your online sportsbook.
We already do it for commuter benefits and lunches and gym memberships.
Go ahead and just give me a 7.5% contribution ceiling.
And while that gets lobbied, this reminds me of a story from college.
One of my teammates was very wealthy.
Generational kinda stuff with like $60,000 in a checking account.
They’d submit NBA games that were already in the 2nd half.
NHL game totals in the 2nd period.
Just obnoxious shit and he accepted every bet and paid every bet out.
This went on for a semester where he lost about $15,000 to teammates.
It reminds me of this coach but the complete opposite where nobody is looking out for anyone.
That can happen if your not careful.
Also, this story is a few years old.
I’m interested - are you in jail, coach?
Is this still going on?
It was a $20 buy in for a $135k pot, pretty big pool.
I entered 10 times for a $200 investment.
About 7 of us decided we wanted to split the pot and walk away with about $8k each.
Of course not at 15 people agreed, so on we went to the next week.
At that point I wanted to split the pot again ($45k each!)
and of course one guy agreed and the other scumbag didnt.
So we had to play out that week.
So I made another deal with the one guy who wanted to split.
It was divisional playoffs and we agreed to pick different teams to increase our chances.
So I was pulling hard for the jets!
So the jets win the game and I end up taking about $67k home.
Now, I need your and the stoolies opinion.
Keep in mind, the deal was if one of us WON we would share some of the winnings.
The whole time reading this I kept thinking about those 6 people he made the original agreement with.
Not the full $8K but still a huge chunk.
Personally I think that’s a remarkably classy move.
You have some issues with a handful for not giving the full load.
But they all crapped out the weekend you made the agreement.
You’re the one that had to navigate the last couple weeks.
You’re the one trying to find an equitable solution.
You’re the one grinding.
That’s why I think the split is just so fuckin solid and generous.
You probably get away at $4K but bumping it to $5K is really all class.
You’re a gentleman and a scholar.
Or is he a sucker?
I haven’t made it this far in any pool situation to rely on personal experience.
Someone coach me up if it’s wrong to support such sportsmanship.
My brain and gut say he did the right thing.
A Family Gathering
So a couple years ago my brother was a sophomore in college.
On December 18th-ish, his psycho girlfriend asked for a $250 jacket for Christmas.
He has maybe $400 to his name, but wanting to make her happy, he bought it.
The day after that, he has surgery on the ACL he tore a month prior.
All in all it was pretty rough 3-day stretch for him.
Since he had surgery, he couldnt move from the couch for 2-3 weeks.
Not a ton of money, but a lot considering how much he had in bank account.
This kid went on the hottest streak I have ever seen.
He went something like 28-4.
My dad started working from our living room because it was absolutely electric.
He made close to $3,000 that break.
Then used that original $250 to buy an autographed Magic Johnson jersey.
Aced both finals too, and never had to put up with his ex-girlfriend again.
Pretty solid winter break.
I’ll take the 28-4 with a grain of salt.
22-10 moves the needle just as much but really that’s not the point.
Let’s just take a minute to recap the brother’s situation.
Spending more money than he has.
Blown ACL with a December recovery.
That’s a tall order, and the only saving grace is Bowl Season and a little action.
Before we even get into what happened, can we just enjoy the presence of sports gambling here.
Like that’s just an awful, terrible, horrible, no good, very bad situation.
And instantly we’re all likeoh that’s not so bad, he can bet every game.
Legitimately most of us all agree that’s a solid backdrop to recovering from everything.
One step further, it’s nice recovering from a surgery at home with mom and dad.
There is no comparison to mom managing the snacks and helping with the painkillers and generally just being there.
The mom updating lines on the white board in the kitchen.
We got parlays and touchdown props and pizza parties for the 7pm’s.
That’s a solid scenario and it’s because you got a good family.
Nothing beats good family although a 5-teamer when you need it comes close.
Can We Get Mad At This?
My buddy and I were sitting around watching college football during rivalry week 2 Saturday’s ago.
Been a pretty even day, some winners, some losers.
Pretty much same shit different week.
All is well right?……WRONG.
No shut the fuck up for a second.
It’s not bullshit.
It’s not bush league.
You didn’t get screwed and there’s no recourse I can support for you.
Truthfully and sincerely, I would argue that you moan out loud often.
This wasn’t in the syllabus!!
I mean what do you expect here?
This is the real world buddy.
You know Tennessee +1700 isn’t real.
Everyone knows it’s not real.
And yet you think the Uniform Commercial Code applies?
That you have some kind of agreement with your offshore illegal sportsbook that they need to honor posted lines?
I got news for you pal.
Everyone is sticking it to you.
The grocery stores and pharmaceutical companies.
The banks and energy companies.
Your employer and the IRS.
Everyone at every level is giving you the business at every opportunity.
On the bright side, at least customer service gave you a heads up.
At least they owned the mistake and made you aware of it.
That’s called taking institutional responsibility and it basically does not exist in today’s world.
So maybe take a minute to appreciate their willingness to own the moment.
Or next time just assume that bet doesn’t count when it clearly doesn’t count.
Either way, you’re in a much better spot than complaining online.
Got a gambling story?
Email it to mecarl@barstoolsports.com