No one in the whole entire country enjoys having to deal with the federal or state tax system.

That says, it is a requirement for pretty much everyone, so you deal with it.

Or in this case, you find a way to bend it to your will.

OP had a friend who was a no-nonsense, by-the-book type.

First, you have to appreciate the kind of guy Nathan is. Brilliant engineer/crazy person. Because Nathan likes rules and Nathan doesn’t give up when he knows how things should work.

I like to get him to tell the story whenever we’re together because he doesn’t even see why it’s funny – it’s just how he deals with all problems.

Nathan was like if you saw Sysiphus and you thought, maybe I should try to stop him. But then one day, the boulder was on top of the hill. And you go and ask Sysiphus how he did it and he replied, “it was simple… I just kept pushing it forever and ever, and eventually… the mountain gave up.”

A real Grade 19 Bureaucrat. He just works systems through problems no matter how daunting they should seem.

Until one day, when Nathan’s unstoppable force met an immovable object. I came into work and saw checks and envelopes spread all over his desk.

And Nathan filling them out with the kind of grin Steve Buscemi might have crossing names off a list with a tube of lipstick.

A while back he prepared his taxes but then forgot to mail the check before he left for China.

I ask him about it and he calmly starts explaining that he’s “having trouble with the IRS.”

I probe a little deeper since that in no way explains more than one check or envelope and he starts telling me about how last year during tax season he was in China for work so he started filling his taxes out early while at his parents’ house.

He owed a little but left before he could mail it in.

He paid online, but his parents tried to help out, causing 2 payments to be sent.

But he remembered while in China and (broke through the firewall in order to) paid it online. But then his parents, thinking he forget, wrote a check for him and mailed his taxes in too.

So now his taxes would be paid twice. So they said don’t worry about it, we’ll cancel the check.

The IRS cancelled the duplicate check, but charged a fee.

Well, it turns out that NYS IRS has a cancelled check fee of something like $40. And they sent Nathan a bill and penalty for the $40…

That was it. That was the whole story. A $40 fee.

OP pointed out he was being charged even though it was his parents’ check.

Nathan, why do you have 20 checks on your desk? “Oh, well after I explained to them what was wrong with the fee they didn’t get it.”

So Nathan spent the next 4 weeks escalating the issue to the point that he got a case officer – a real, live human agent on the phone with a case number.

Nathan started by asking for the agent to spell his name – and politely to demonstrate that he was where he said he was by asking how the weather was and how the “drive in” had been that day.

He then asked for his agent’s manager – got their name and exchanged some pleasantries.

He explained that his parents wrote the check but that he was the one being charged the fee.

The agent explained that this was the policy of the IRS – “All cancelled checks will result in a $40 fee”.

The agent and Nathan went in rigorously compliant circles for hours exploring the rules.

He made a point about how silly this was in a very impactful way.

Nathan then calmly confirmed that:

It is the policy of the IRS to allow just anyone to write a check on behalf of anyone else – “yes sir that is fine. You just need to indicate the name and zip code of the account.”

It is the policy of the IRS to charge a $40 cancellation fee to the person whose account is indicated on the check. – “yes sir, that is the policy in NYS”.

This means that – and I swear to God he actually asked the agent this hypothetical on the phone – “I (Nathan) could write a $10 check and indicate it’s for you (Mr. “Agent” at 1234567 Schenectady, NY) and cancel it resulting in a $40 fee for you with absolutely no penalty or recourse to me?” –

The equally compliant and rule-minded agent replied, “Yes sir, I guess you could.”

So, that’s what Nathan did. And that’s what was doing with 20 checks on his desk and what he meant by “IRS trouble”.

He was following through… sending checks to the IRS addressed to pay the taxes of the agent and the agent’s manager – so Nathan could cancel them, causing the agent and his manager to owe the IRS a fee for each cancelled check.

He was exploiting the same flaw in the system in which he was caught to essentially extort the IRS agents.

His fee was ultimately returned.

I laughed about this for weeks after…

And then… 3 or so weeks later… I’ll be damned if he didn’t receive a letter from the IRS:

“Sir, we understand the point you’ve made. Please consider your fee waived and I hope we can put this behind us.”

TL;DR: My Co-Worker got the IRS to reverse a fee because he found a way to use a loophole to force the IRS Agent to have to pay the fee too.

Everyone must love getting one over on the IRS!

Reddit is saying this is “awesomely evil.”

And they kind of love that he went to all of this effort over $40.

The fact that he’s not doing anything illegal makes it 10x better.

Let’s not get carried away.

They all agree it’s hard to pull one over on the government!

This is a story for everyone.

I could read it again and again!

If you liked this post, check out this story about an employee who got revenge on a co-worker who kept grading their work suspiciously low.