I haven’t filed my income tax return before October 15 in more than 20 years. April 15 is an impossibility, partly because I haven’t gotten all my K-1s by then (crappy private investments and real estate deals I’m underwater in), but mostly because I dread the enervating fight every year with my accountants. The problem is, by procrastinating until October 15, I give up any leverage I might otherwise have, and I’m forced to pay pretty much whatever the accountants say I owe.

There was a time when preparing my tax return was like solving an algebra problem for which there is one correct answer—and the IRS gave partial credit if you showed your work. Now it’s a complex dance routine with the accountants. And I’m a white man.

Anyway, this year would be different. I would make my stand on my estimated taxes and wage a strategic battle before April 15, leaving a victory mop-up operation for October. I wasn’t particularly paying attention when an accountant whose name I didn’t recognize phoned to tell me the dollar amount of the check I would have to write for my estimated tax return. My head snapped around so sharply that I almost cracked a veneer. “Go to hell!” I shouted. “You’re fired! How dare you! Who are you? I’m calling Larry right this minute!” I had planned on showing some histrionics as a negotiating ploy, but this was a shocking amount. I slammed the phone down mid-sentence as my voice started to rise to a girlish squeak.

Larry is a close friend and the managing partner of the accounting firm I use. He likes to put up-and-coming junior managers on my account to test their mettle. I went to the office kitchen and poured myself two fingers of The Balvenie 21 to make myself right. I can take this punk, I thought, draining the glass.

I called him back. “Jeff,” I said soothingly. “Listen, I have to apologize for that outburst. It’s been a hard day, and you caught me off guard. That really was a nasty number you mentioned.” I tried to make conversation, draw him out. “You know, that reminds me of something H.L. Hunt once said. We should get one vote for each dollar of tax that we pay. It’s insane that my yardman’s vote for Hillary can cancel out my vote for McCain.”

There was silence on his end. At length, he finally said, “I seriously doubt that your yardman can vote.” He clearly wasn’t a conversationalist. “Jeff, how long have you been with the firm? Did Larry hire you personally? I thought so. Larry prizes creative problem-solving.” Was I spreading it on thick? Sure, but this geek had probably never had more than a 15-minute conversation with a normal human being without chewing a pencil in half. I had flashbacks to Mistral, 1983. I was in full seduction mode.

“Jeff, my assistant probably didn’t give you all my construction draw statements on the renovations of my home office. And of course, there was the trip to Virgin Gorda to inspect the marina that we invested in. You don’t have all the facts.”

He countered with that flat accountant voice: “The marina is on St. John’s. You cannot expense a family vacation to the British Virgin Islands. And the home office expense was long ago settled in IRS Public Notice 93-12 as being nondeductible if you have a business office from which you regularly conduct your trade or business.”

I’ve always felt that citing statute was the last refuge of the scoundrel. “Jeff,” I responded with a little edge in my voice, “it seems like I’m the only one proposing ideas here. I hire your firm for innovative tax strategy. I could have my secretary get on the TurboTax site if that’s what we’re talking about here.”

This struck a chord. In the end, we were able to chop about a quarter off the original amount by making use of some investment losses that I had stashed away for a rainy day, and by constructing a plausible argument for the deferral of a chunk of my income. “But,” Jeff said, “deferral is not elimination. We’ll be having this discussion next year.”

Right-o, chap, I thought. I’ll have another six months before October to bring you around. Next year can take care of itself.

Later that night, I was complaining to my wife about the injustice of the current tax system and how hard we’d been hit this year. “Someone has to pay for Bill Clinton’s Secret Service detail,” she replied. She really knows how to twist the knife.

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