Uncle Sam’s gonna want my apples…

You know that old saying that “money doesn’t come for free”?

Yeah.  I think that’s going to happen to me when I file my taxes next year.

Let me explain.

I already mentioned that when the Stir Crazy trivia team (including yours truly) won the World Tavern Trivia Championships in Atlantic City last year, all the team members (including yours truly) had to fill out W-9 forms before we could receive our greenbacks.  For all intents and purposes, let’s just say I received several “apples” for my participation on the team.

Okay.  I can live with that.

The other day, I took a “Chuck needs to get away from everybody” moment and visited the Saratoga Harness track – yes, I know it’s now branded as “Saratoga Casino and Hotel,” thanks for reminding me – and I chose to play some penny slot machines.  Figured I’d just go through the motions, watch the numbers almost come up in a tantalizing, teasing taunt and torment…

And then this happened.

Look at that.  More 7’s than at a Seagram’s bottling plant.

I can’t be that lucky.  Get off that slot machine before that $150 earned becomes $150 lost.  I went to another slot machine, and before i knew it …

The damn machine hit a jackpot.

And I’m thinking, “Woo hoo I can pay off my car loan even quicker now!”

And I’m also thinking, “Okay, Chuck, now walk away from the machine.  Treat yourself to the buffet and head home.  Don’t press your luck.”

As I was about to press the “cash out” button and receive my payment voucher, the machine actually spit out a second voucher – a “limited voucher,” as it was.

I couldn’t just cash this voucher.  I had to actually go to the cash cage and fill out another tax form to claim the money.

Seriously?  Okay, okay, name, address, Social Security number, here you go, I’ll take that in crisp $100’s please, they’re going to go to my bank anyway…

But now, as I’m feeling like a high roller and plotting my high-rolling escape from the casino, I’m thinking to myself…

All these winnings … and all these tax forms … am I going to get socked by Uncle Sam next year?

And I recall something that happened to an old friend of mine, who for this blog shall be known as Rachel.  One of Rachel’s relatives passed away and left her a nice inheritance.  Of course, Rachel did what many people do when they receive large sums of money – she spent it like it was on fire.  And the next year, when she filled out her taxes, she didn’t claim the inheritance on her tax forms.  The IRS already knew she received money from the inheritance and were waiting for their financial take.  Rachel spent the next few tax sessions working on a payment plan to pay off her IRS debt.  Urgh.

I don’t want that happening to me.

So on the way home from the track…

I called my Uncle Sam.

“Sam” is the name of my tax preparer.  It’s a personal nod to a time when, as a kid, my Grandma Betty told me she had to go visit her Uncle Sam the tax man for some tax matters, and wanted to take me downtown to meet him.  Of course, seven-year-old me is thinking that “Uncle Sam” has the star spangled suit and the big top hat and the pointed white beard…

No.  “Uncle Sam” was a tax preparer named Sam Sexes, he had to be 90 years old if he was a day, and his office was in a dingy part of downtown Boston.  Not even a star spangled top hat in sight.

But for me, the tax man always earned the nickname of “Uncle Sam,” no matter who he or she was in real life.

And after speaking with “Uncle Sam,” I received some answers.

First, as for my Atlantic City winnings – because I did not have to pay a fee to enter this tournament, winning the money isn’t considered a gambling prize.  So I have to claim that trivia championship money on my tax form next year.

As for my Saratoga winnings – those are considered gambling winnings, and in 2018 I should receive an itemized report from the casino about how much money I’ve won and lost there.  You know that little “loyalty card” you receive from the casino, the one you’re supposed to insert in the slot machines, the one for which you can earn points towards discounts at the all-you-can-gorge buffet?  Yeah, that’s how the casino knows how much you’ve won and lost.  Right down to the penny.  So I could claim some deductions for gambling losses, which may or may not balance off what I’ve won there.

Damn this is confusing.

But the smartest thing for me to do … and let’s face it, I gotta be smart about all this … is to set aside a portion of my filthy lucre for Uncle Sam.  Whether Uncle Sam is my tax preparer or the beancounter in Washington who examines my filed returns … I have to be pragmatic about things.

I also have to understand that I’m NOT going to win at the casino every time I visit it.  I’m NOT going to pick the winning horse just because I stick to my plan of always betting on Horse #5.  Although that did kinda work for this race…

Because, as I said at the beginning of this blog post … money doesn’t come for free.  That’s why they call it income tax.  Because income the taxman and outcome your coinage.

And as much as these windfalls are beneficial for me – and they help to pay off the Dracourage car loan and pay for a new laptop – these windfalls can disappear like the wind.

And I don’t want to fall in the wind.  Not even in a stiff breeze.

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