Opinion: We need the sharpest pencils in the drawer
Dan Conaway
Dan Conaway was a freelance columnist with The Daily Memphian from 2018 to 2025.
I don’t do my own taxes.
In fact, my taxes send TurboTax into default mode, crash laptops, and fry transformers. H&R Block blocks my phone number. My accountant does my taxes, only because she knows me, she speaks Dan, and she may very well use the Gordian knots in my finances to train people in her office.
You see, in 2002 my company bookkeeper – let’s just call him Voldemort – cooked my books to the tune of a million-six in unpaid payroll taxes. To the IRS, not paying payroll taxes is a capital crime, you know, like killing your entire family. With an ax. In church. Needless to say, the IRS and I have become close in the ensuing years. Love letter close, without the love. Stalker close, without the restraining order. Siamese twins close, without the family connection.
As to the effect on my taxes, well, it’s complicated.
A few years ago, my lawyer and I met with the IRS to finally settle the whole mess – the same lawyer I’ve praised before for telling the IRS in another earlier meeting that I was “as broke as the Ten Commandments.”
It’s a rare lawyer indeed who can be funny in an IRS meeting.
This time, the agent who entered the room under a buzzing fluorescent light was poured into an undersized golf shirt and carrying a coffee-stained file folder and a pencil. After the usual niceties – verifying my name, Social Security number and the immense size of my transgression in societal and monetary terms – he rifled through the file, turned a page over, and started scribbling on the back with the pencil.
He then informed us of what he expected of me in reasonable monthly payments based on my income – an amount well north of reasonable and based on somebody else’s income, more like the Donald’s than the Dan’s.
We questioned his figures and offered ours. He started scribbling again. The pencil broke. We both offered our phone calculators. He said using our phones would be illegal, and excused himself. He returned with an antique calculator – the pride of Texas Instruments ca. 1976, trailing a cord wrapped in electrical tape – and tried to plug it in. The cord wouldn’t reach, so he moved his chair closer to the outlet, put the museum piece in his lap, and ran some numbers.
It’s a rare occasion indeed when something happens in an IRS meeting that you have to chew your knuckles and avoid eye contact to keep from laughing.
Here’s my point, and thank you for waiting.
It seems past president Trump has some tax problems. I can relate. In fact, it seems we also seem to have had the same kind of chief financial officer – one better on a cooking show than in the office – one twisting the law like some enormous fresh-baked cruller – turning the truth into a dark, impenetrable roux of deceit.
There are a number of differences: the number of zeroes between the totals in Trump’s cooked books and mine, the fact that I knew nothing about my bookkeeper’s crime, and the further fact that I took responsibility for it as the head of the company, and in so doing, I lost that company.
I never lied. The pain remains. So does my dignity, the worth of which has to be determined by each of us.
The reason that people like our past president can get away with willfully gaming the system, breaking the law, and stealing from you and me in astounding amounts with breathtaking frequency over the entire history of his hubris-soaked, lie-fueled enterprise is the joke we’ve allowed the IRS to become.
The larger the crime and the more time and money thrown at its defense the more likely the victory. The IRS doesn’t have the resources, the inclination or, quite frankly, the acumen to take on thieves with the size and chutzpah and amoral dedication of Trump.
Much of the country cheers him on, the irony that he’s stealing their money and denying their country viability and stability lost on them. Again. And again.
Trump isn’t being brought down by the IRS. If he goes down, it will be at the hands of the United States Attorney for the Southern District of New York. If he does, every American will win.
Every IRS budget cut, every denial of resources, every performance of tax-hating political theater, every promotion based on tenure rather than ability, assures us of – at best – an overworked and underpaid IRS, and – at worst – an incompetent and code-choked clown school.
In the one agency that most affects us all, we should put our very sharpest pencils in every drawer. Subtracting support simply doesn’t add up.
I’m a Memphian, and the IRS and I have agreed to start seeing other people.
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