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Taxes and Bombs:
Tale of a Dark Night in April

Is filing your taxes an explosive issue? Put your April Angst in perspective by joining us on a visit to an free agent murder-and-arson lawyer.

By Lawrence San

A trenchcoated man stalks the shadows in a rain-dark alley; a mad bomber tinkers with tubes and wires in his basement; a prosecutor slams the bars on a prisoner crying his innocence. We associate such images with 1930s movies, not with our own lives, but at least once every year -- usually in April -- free agents have a first hand experience of film noir.














This story evolved from an interview about options for doing your taxes.

A trenchcoated man stalks the shadows in a rain-dark alley; a mad bomber tinkers with tubes and wires in his basement; a prosecutor slams the bars on a prisoner crying his innocence. We associate such images with 1930's movies, not with our own lives. Free agents may be an adventurous lot but not that way; most of us pursue our craft relatively unencumbered by fears of the law -- except once a year when we do our taxes.

To the average wage slave with a relatively cut-and-dried tax return, a free agent's tax angst is merely a mystery; but for many free agents, taxes are a swamp of complex decisions, a kind of multi-layered bad dream:

In the foreground of our minds are the specific tax decisions to be made, and the uncertainties that make those decisions difficult. Further down lurks the nauseating possibility of being summoned to a full-dress audit by the IRS, of having to defend one's decisions while being interrogated like a criminal suspect. At the deepest level -- so deep that most of us never consciously face it -- is the awful knowledge that every year some free agents get locked in prison simply because of little ink marks, the wrong little pen scratches they made on their tax returns. As unlikely a possibility as this seems, tax time is still the moment when most of us come closest -- the merest graze, as it were -- to the world of trenchcoated investigators and prison bars, the dark rainswept alleys of our legal nightmares.

It's precisely this weird emotional juxtaposition of routine bookkeeping with film noir that makes Jefferson Boone so interesting. He's an free agent lawyer who handles "darkside" criminal cases most of the year, who lives in the world of tough prosecutors and slamming prison doors -- but every spring, improbably, dons an accountant hat and prepares tax returns for free agents.

It's nighttime after a long day's work at the office. Boone leans far back in his chair, the jacket of his rumpled three-piece suit hanging open, but he looks neither relaxed nor tired. He stares intently at his visitor while shuffling through papers, puffing at a cigarette dangling from his mouth, and answering the phone. The phone is still ringing even though it's late at night -- and the calls are obviously from clients. He handles them swiftly with a few muttered words, and turns back to the visitor. Prompted by a question, Boone suddenly swivels his chair 90 degrees and, with his face in profile, starts surfing the web. The blue light from the monitor shines almost eerily through the clouds of cigarette smoke to illuminate the late-night stubble on his face. He surfs and smokes and talks all at the same time. Boone stutters when he talks, sometimes badly, but any effect of vulnerability this might evoke is quickly dispelled by his words.

The clients who fidget in his waiting room mostly don't wear suits, and you wouldn't expect them to: Jefferson Boone isn't a corporate type. He's a neighborhood lawyer, and Allston, Mass. is one of Boston's artistic havens. Unlike the fashionable gallery zones downtown, Allston's artiness is of the gritty kind; you can imagine struggling painters living here, but not yuppie art buyers. It's a hard urban place where the streets teem with poor students and musicians and third-world immigrants. Down the block from Boone's law office are grimy storefront art galleries. Surprisingly, they're not selling schlock: their windows display powerfully expressive African masks and strange corroded-metal sculptures and violent-looking cult-ritual objects. Around the corner, bars featuring local rock or blues or ethnic bands nestle next to exotic restaurants serving third-world food at bargain prices.

Boone's law office is in rented space on the second floor of a converted two-story bank building. His office suite looks neither corporate nor storefront-gritty. It's more like a polished loft space, complete with the interesting architectural anachronisms one often finds in such spaces: old, factory-style concrete ceiling beams next to modernistic stairwells, antique red-brick arches peeping out from behind rows of current law books. It's the kind of space you'd associate with a successful artist, not with a lawyer. Boone (who, years ago, was a photographer before he became a lawyer) says he designed the space himself. In fact, he's highly self-sufficient in general. The door says "Boone & Henkoff," but his young partner died suddenly years ago of food poisoning contracted in Mexico. An assistant sits in the waiting room and helps with administrative tasks, but Boone says he's given up his attempts to hire and work with other lawyers, and now accepts his role as a sole practitioner. When introduced to the term "free agent", he immediately picks up on it and applies it to himself and many of his small clients.

Like most neighborhood lawyers, Jefferson Boone does a little of everything, but he's probably best known around town for his high-profile murder and arson cases. He defended the famous Roslindale Bomb Case in which one cop was killed and another lost an eye. It's a complicated story featuring a father and son both named Thomas Shay; Boone represented the younger Shay and still hotly proclaims his innocence while Tommy rots in jail. Other than murder investigations, Boone's great passions include photography and arson. He reminisces about mysterious fires and break-ins. But today we're here to talk about tax strategies. Although not a CPA, Boone is a trained accountant, and every year around tax time he transforms himself into a tax advisor and preparer. Most of his tax clients are people he already has some other relationship with. In a typical year, there are six or seven are full-time free agents, another five or ten sideline as free agents.

Boone stutters badly, and his difficulty in forcing out the words contrasts oddly with his ability to reel off organized lists of key points while constructing a linear and persuasive argument. There's a related but even odder contrast: we tend to associate stuttering with a kind of timidity, with a lack of certainty, but there's nothing timid or uncertain about this man. In some ways, he seems almost the stereotype of an aggressive lawyer.

Boone exhales clouds of smoke while struggling to squeeze out phrases, and you're forced to just sit patiently and wait. When the phrases do finally come out, he's actually quite articulate -- it's something like looking at a not-quite-assembled jigsaw puzzle but still being able to see the picture, or like a skip in an old-fashioned record that's unrelated to the music itself. Boone speaks at length about free agent tax issues, and has strong opinions on the subject, but it's a strange conversation: even as we speak, the Roslindale case is playing out in the courts for the second time. He's no longer Shay's lawyer, but he still cares about his former client and still proclaims his innocence. It's unlikely that Boone's emotions are focused on tax issues, but, valiantly, he sticks to the tax topic.

It's weeks later, and the second bomb trial has just ended abruptly. Jefferson Boone sits hunched over his desk, chain-smoking and reading a letter. It's from Thomas Shay Jr., the convicted Roslindale Bomber. "Tommy," as Boone calls him, has just pleaded guilty during the second trial to avoid the possibility of a longer prison term. In the letter to Boone he proclaims his innocence still. Boone is furious at what he perceives as a massive miscarriage of justice; he rages at the new lawyer, at accidents of timing that screwed up the investigation, at the men walking free whom he suspects are the real bombers.

It's the time of year when Boone has donned his accountant hat and is supposed to be thinking about deductions and exemptions, but somehow this seems improbable right now. Outside his windows it's pitch black and the music bars are closing; drunken students with false ID cards pour, laughing and yelling, into the dark street. They barely notice the beaten old drunks slumped along the sidewalk or the recent arrivals clustered on street corners, immigrants who are more likely to be whispering about the INS (Immigration and Naturalization Service) than the IRS. In addition to students and immigrants, Allston has many free agents, especially in cultural fields like music and the visual arts. They tend to be young and nocturnally social; it seems unlikely that many of them are thinking about taxes this night either. Can the faceless IRS and its bureaucratic rules really mean anything to people -- even in tax season -- in this funky neighborhood with its struggling artists and micro-business free agents?

A hint of fog swirls above the rain-slick Allston sidewalk; hooded streetlights cast shimmering pools of light into the puddles. Down the block, a flickering lamp in the window of a tiny used bookstore reveals old-fashioned mystery novels with lurid covers and clichéd pseudo-noir writing -- what trash! Next to the bookstore is a twisting narrow alley, where vaguely moving shapes -- barely visible through the night rain but hinting of risk -- lurk menacingly. The bars' flashing red neon lights intermittently reveal crazed derelicts huddled in doorways, babbling to themselves and screaming at passersby, their shattered lives far beyond tax returns, their nightmares deeper than bookkeeping or even bombings. The light in Boone's office shines still. The black rain will lash his office windows for hours while he stutters and rages about his imprisoned former client, but in the end he'll have to turn his mind away from bombs and murder. He's not a criminal lawyer tonight. It's tax season.

Lawrence San rarely writes about (or even talks to) lawyers, but he does write a regular column called inSANity. Other than that, he pretends to be Editor-in-Chief and Creative Director of 1099.   April '99

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