Look at me today and you see a model taxpayer — I dutifully file every year, and usually get a refund. This, however, was not always the case. For years I was a tax scofflaw, out of the System and proud of it! And then fate — in the guise of my temp agency — brought me to Bob Shelby.
If you had seen my boss in those days — if you had seen Bob Shelby ambling down the corridor to his office — I don’t think you would have made much of him. A tall guy — kind of nondescript. White. Very white. Extremely white. Reflecting perhaps 30 percent more light than actually hit him. White. And a bit hunched over — you know, from partner money.
And if you had watched him go inside his office, you might have stood outside and thought, “Oh, he’s just a guy — a golfer, maybe.” But if you had followed Bob inside his office, and had seen him surrounded by his beloved tax documents, I think you would have understood something: you would have understood that this Bob Shelby was no milquetoast. No, this Bob Shelby was a virile, passionate practitioner of the taxation arts. And the thing that got him going — the thing that activated Bob — was this: the U.S. tax code.
Now, if you’re like me, and you were to try to read the U.S. tax code, you might find it, I would venture to say, somewhat dry. But to Bob it was anything but dry. Because what Bob would do is, he’d find two code sections that were supposed to be right next to each other — welded tight — and he’d find just the tiniest little hairline crack between them, and he’d take his little wedge, and he’d wiggle that wedge into the crack between those two code sections, wiggle and worry the wedge, pushing those code sections farther and farther apart — until finally they were so far apart, you could push through billions of dollars in tax breaks.
That’s why Bob got the big bucks.
And once I realized the kind of tax excitement that was going on in Bob’s office, in truth I would have paid just to sit outside and be his secretary. But I got paid. In fact, I even got paid overtime on those special evenings when there was a deal deadline.
Usually, early in the evening, the corporate clients would shuffle languidly into Bob’s office, the door would shut, and then I’d hear from inside his office the “click click click click click” of Bob’s marker on the whiteboard. “Click click click click click” — as Bob worked out the tax ramifications of the deal … and made them go away. “Click click click click click.”
Often, after a couple of hours, Bob would call me into his office: “Josh, I need your help. I want you to go down the hallway to the Tax
Library. In 1903, there was a case that was heard before a rural Wisconsin tax court. I’d like you to grab that case for me; would you, Josh?”
Well, I’d go and retrieve it. I mean, my mom’s a librarian: You give me the number of a book — it doesn’t matter what kind of library — I’ll go and get it. I’d bring it back to Bob …
And this is the cutest thing I can tell you about Bob: Each time, he would treat it as if it had been my idea:
“Why, Josh — yeah! Nineteen oh three — very good, Josh! I think I know where you’re going with this! Based on this 1903 Cheese Mold Ruling, I think we may very well be able to trigger a ‘shotgun provision.’”
I’d go back to my desk. Shotgun provision — that sounds really cool! Of course, I’d have no idea what a shotgun provision was, but it certainly sounded cool. Shotgun provision! “You done knocked up my daughter!” Shotgun provision — sounds very exciting!
I’d listen for the sounds of gunshots exploding from inside his office, but all I’d hear was more of the “click click click click click” of Bob’s marker on whiteboard — “click click click” — until a couple hours later, Bob would again call me into his office:
“Josh, we couldn’t trigger the shotgun. I’d like you to go back down the hallway to the Tax Library. In 1913, right after the codification of our U.S. income tax, there were some loose ends that got memorialized in a Revenue Ruling. I’d like you to grab it for me.”
Soon thereafter, I returned: “Here’s your ‘Rev Rule,’ Bob!”
“Josh — this time you have truly outdone yourself. Because, thanks to this 1913 Rev Rule, I think we may very well be able to trigger a ‘collapsible corporation’ ruling!”
I’d go back to my desk. This was sounding better and better. “Collapsible corporation” — it sounded like what my leftie parents had always wanted!
Now I’d be on the edge of my seat, listening for the sounds of corporations collapsing. I’m easily deluded about myself: I’d start to think, “Maybe it was my idea!” And I’d want my idea to work! I’d start to forget things — little things, such as the fact that I’m nominally against capitalism. I’d want my bad guys to beat the other bad guys. … But all I’d hear was more of the “click click click click click” of Bob’s marker on whiteboard — “click click click click click” — until Bob once again called me into his office:
“Josh, we couldn’t collapse the corporation — but I think we still have just enough time to pull this iron out of the fire. Listen very closely: In 1924…”
“1924 — that’s the year my dad was born!”
“Interesting information, Josh — we don’t need it right now, but thanks. In 1924, a Private Letter Ruling was issued, and based on this 1924 PLR. I think we may very well be able to wheel out our heaviest artillery yet. I think we may very well be able to use the ‘Reverse Double Dummy Maneuver’!”
Back to my desk. “Reverse Double Dummy Maneuver”! I would have imagined that even a single dummy would have been enough. But double? Probably twice as good. And I bet they’d expect you to go forward with the dummy — so to reverse it, very tricky, very clever, I’m digging it…
But again, all I hear is more “click click clicking” of Bob’s marker on the whiteboard. I’m thinking, “Is he actually going to make it this time?” When, finally, right before the deadline, a roar comes from Bob’s office, and Bob comes staggering out — loosening his tie; his collar’s open and his face is all flushed.
He goes, “Josh, it worked! The 1924 PLR! It worked, Josh! We won! Josh, that’s why I love tax law!!”
So don’t try telling me tax law is boring, okay? Because I was there. I saw what it did for Bob.
And knowing how much he cared, one day I mentioned my own tax situation to him: “You know, Bob, I actually haven’t filed in seven years.”
“Josh, I don’t understand. You’re a thoughtful guy — how could you go seven years without filing?”
“It was easy. In fact, it was natural.”
Because, you see, my very first job out of college, I worked as a salaried copy editor for a newspaper. And at the end of that first year — in which I had earned 11,000 bucks — I got my very first “Important Tax Document Enclosed.” And I did what everybody else was doing: I attached it to my 1040, sent it in — and I got a refund! So the next year I did the same thing — and again, I got refund.
But the year after that, someone in the newsroom — I don’t remember exactly who, let’s just say it was Satan — someone came up to me and went, “Josh, tax time’s a-coming. I assume you’re going to be itemizing this year.”
“Itemizing? What’s that, Satan?”
“Well, you see, Josh, now that you’re not just a salaried copy editor but also a freelance television critic, you can file a Schedule C and deduct your legitimate business expenses. If you don’t deduct your business expenses, Josh, you’ll be taking money out of your own pocket.”
Taking money out of my own pocket?! That’s a weird and circular movement, and I won’t do it!
So I went home, waded as usual through the pot smoke of my roommates, shut the door, and looked around my room. What was a “legitimate business expense”? Okay, I’m a television critic, so … the television! Yes! Because I need something to criticize!
Okay, so the television … And then, yeah, the DVR, because I can’t catch every episode of “T.J. Hooker.”
And, of course, the DVDs. And the replacement labels for the cases, which I get from Radio Shack. Oh! — and the TV Guide, which guides me to the television! And the books of television criticism I’ve bought. And, actually, the books I’ve bought that aren’t television criticism: They’ve still informed my criticism of the television. Oh! — and the chair I sit in, of course; very important what my posture is when I criticize a television. And the food I eat — which literally makes up the cells that form the critic of the television.
I started looking around my room with increasing franticness: I didn’t want to miss a single last deduction! I started to feel like the Gene Hackman character in “The Conversation.” I thought, “If I miss a single last deduction, I’m taking money out of my own pocket!” Until finally I blew a gasket!
And I did not file.
And nothing happened.
So, the next year, looking for some consistency in my life, I again did not file — and again nothing happened. And the seven years followed quite smoothly.
“Well, Josh,” said Bob, “it’s got to end now. You have to take care of this tax thing, and pronto.”
What could I do? I didn’t want to stop working for Bob — and miss out on all that tax excitement, not to mention the free coffee and endless supply of uniball micro pens.
So I filed. And the next year — looking for some consistency in my life — I filed again. And the years since then have followed quite smoothly.