Dante’s Way (Sul percorso di Dante)

by Ron Singer

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Until my “retirement” thirteen years ago, I enjoyed a successful career as an actuary. Concurrently, I enjoyed an avocation as an amateur Dante scholar, an avocation I have since had more time to indulge. In fact, I am a charter member of the Metropolitan Alighieri Dante Society (MADS).

Here are a few details from the life and work of the Master that are germane to my story. Dante commences his poetic journey of revenge and redemption in the throes of a mid-life crisis:

Nel mezzo del cammin di nostra vita
mi rirovai per una selva oscura (Inf. 1.1-2)

Or (in my own translation):

In the midst of life’s journey,
I found myself lost in a dark wood.

By the time he began his masterwork, Divina Commedia, he was languishing in exile:

Tu proverai sì come sa di sale
lo pane altrui, e come è duro calle
lo scendere e ’l salir per l’altrui scale. (Par. 17.55-60)

As the proverb goes, how salty the bread
in another man’s house,
how steep the stairs!

The principle of revenge in Inferno, the first of the three books that comprise the Commedia, is called “contrapasso”: i.e., the punishment mirrors the crime. Yet the actual punishments that are meted out are often harsher, or less harsh, than the sinners would appear to deserve, even by the standards of early 14th century Italy. In many cases, Dante’s own loyalties, passions, and quirks richly dye the contrapassi, as do the sinners’ motives, virtues and emotions.

Take the “outing” of his beloved teacher, Brunetto Latini, who languishes in the Seventh Circle, reserved for those who have sinned against nature. This particular judgment is tempered in several ways. Looking down from a ridge above the one on which Brunetto must endlessly walk and burn, the contrapasso for “cruising,” the pupil expresses his respect:

Io non osava scender de la strada
per andar par di lui; ma ‘I capo chino
tenea com’uom che reverente vada.

‘Though I dared not leave the upper path
to walk the lower one with him, I kept
my head bowed, as one who walks in reverence. (Inf. 15.43-45)

After prophesying his visitor’s future woes, the political feuds that will drive him into exile, Brunetto alludes vaguely to his own sin:
In somma sappi che tutti fur cherci
e literati grandi e di gran fama,
d’un peccato medesmo al mondo lerci. (Inf. 15.106-08)

In sum, note that they were all clergy
or renowned scholars, befouled on earth by a single sin.

Note, too, the implicit boastfulness of “renowned scholars.”

Brunetto further mutes his transgressions by graphically dissociating them from those committed by other gay men, including a sinner in the employ of Dante’s archenemy, the “servant of servants,” Pope Boniface VIII:

…e vidervi
s’avessi avuto di tal tigna brama,

colui potei che dal servo de’ service
fu transmutato d’Arno in Bacchiglione,
dove lascio li mal protesi nervi. (Inf. 15.110-14)

…And if you had shown
a hankering for such filth, you might have seen

the one transferred by that servant of servants
from the Arno to the Bacchiglione,
where his sin-stretched organ finally expired.

In somma, one might say, Inferno is the work of an angry man who, having lost his way in life, is groping for truth and justice. But, even so, it is the prevailing malice (e.g. the incidental jabs at Boniface and his minion) that has endeared the book to seven centuries of readers –myself, included. In my case, a further reason the book speaks to me may be that, like the poet, I seem to have lost my way, and taken solace in revenge, though closer to the end of life than to the middle.

As another aside that I hope will prove illuminating (we old men are garrulous!), let me recall Dostoevsky’s Underground Man. Quoting from memory this time, and in my own loose translation, ”I am a sick and spiteful man. I think my liver may be diseased.” That’s me, except for the liver. Mine is fine, which is more than can be said for some of my other body parts.

Who am I, then? By name, Paul Wolf, I am an octogenarian whose years in exile on the island of old age (increasingly populous, nowadays) are about to end. My life was not, of course, always so. As mentioned, I spent my working years as an actuary. My single employer for more than four decades was what is called a “super-cat” re-insurance company. Specifically, my job was to use stochastic calculus, a branch of mathematics, to calculate the odds and costs of likely natural disasters, and to help my masters determine the rates at which they could very profitably re-insure companies that sold primary insurance against these disasters.

Over all the years, and especially near the end, with the advent of severe climate change, there had certainly been no shortage of catastrophes. But, contrary to popular opinion, the most successful super-cat re-insurance companies make more money when catastrophes proliferate –if they have good actuaries, that is, not to mention large capital reserves, or, as a contemporary vulgarism puts it, “deep pockets” (which is, strictly speaking, a dental term. I know about those from personal experience. The treatment is excruciating.)

Speaking of “deep pockets,” as a highly competent senior employee, I was amply rewarded. Over the years, I was able to amass savings which, invested wisely, of course, would have enabled me to live very comfortably in retirement. But, owing to a major setback, what I came to desire more than money was to make those who had offended me live very uncomfortably. Not as uncomfortably, perhaps, as Dante’s souls in Hell, but very uncomfortably. Actually (or, if you a devotee’ of paronomasia, or puns, actuarially), it was my own masters against whom my wrath was directed. Although I hope you will agree that I had good cause, and that the plans for my revenge were clever, there is a strong probability that these plans are about to come to an end that is… catastrophic.

The precipitating incident took place at 9:15 a.m. thirteen years, two months, and four days ago. This, coincidentally or not, is the same time of day that I now sit here at my keyboard. Without any notice, whatsoever, I was summoned to the Personnel Director’s office.

I knew what was coming. First, my workload had been steadily increasing for sixty-three months, as my greedy employers relentlessly downsized my department. Until four months before my summons, two survivors, both of us very senior, had been doing the work previously done by five, then four, then three. Two months after that, my co-survivor, a highly competent woman about ten years younger than I (i.e. in her early 60’s), also disappeared. The next morning, a bright young thing was already ensconced at her predecessor’s desk, sharpening multitudinous virgin pencils. (We still used them, in our “game.”) I was introduced to the new employee by the Office Manager, who directed me to “show this newbie the ropes.”

“Newbie!” Yet another neologism! And never mind the nautical cliché! Don’t you love what is happening to the mother tongue? (Or is it, by now, the “parental” tongue?) Not that I am a prescriptive grammarian, someone, that is, who still believes English should assume the ostrich position, but the current rate of change is ridiculous. If languages were motor vehicles, there would be a massive pile-up on the Highway of Discourse.

At any rate, for me, “showing the ropes” was, to mix the metaphor, the handwriting on the wall. My own meeting with the new Personnel Director took place six weeks later. This would be the first time I had met her (“Laid eyes on her” sounds faintly salacious.)

“Hello, Paul,” said the smooth-faced, forty-something African-American, offering me a firm handshake. “I have good news and bad news for you today.”

As usual, the company had covered its bases, or its backside: a female of color, no less, in middle management! As for her “good news and bad news,” we used to call such phrases “see-saw clichés,” other examples being “hale and hearty,” and “fat and forty.” Whether hale or hearty, the new P.D., though forty, was anything but fat. Au contraire, she looked very trim in her black “power” suit (most definitely not a “Black Power” suit!). Her empathic smile could have illuminated the Empire State building. Were her teeth capped, or did she have good dental genes?

To skip the bulk of our short conversation –a monologue, really, interspersed with a few grunts from me– the good news was that my parachute would be quite generous, about 18-karat. The bad news was obvious.

Less obvious was the contrapasso I devised. About a month after my “termination” (not starring Arnold Schwarzenegger), I began to set a plan in motion. I was surprised to discover how easy it would be to get even with those ingrates, my ex-employers.

(Not) to divulge trade secrets, but I realized the firing process had been uncharacteristically sloppy. Yes, they had made me sign some forms: a guarantee of non-disclosure of proprietary methods; abdication of the right to work for competitors (with a long list of rivals, plus “any others”); a pledge not to contact any of the firm’s other employees, past or present; and so forth. As most people know, forms like these carry varying amounts of legal weight, from zero, to “not if you have a decent lawyer.” The only one that counted, the stricture against contact with other employees, could have been demolished in court by a summer intern. But, as I already realized, if the scheme I was about to undertake misfired, I might need not a lawyer, but an undertaker.

Even more remiss, perhaps, was the company’s failure to change the locks. To make a long story short (I know, this one is already 1,650 words, and counting), I decided to contact my two immediate predecessors on the chopping block. As Google informed me, both were still among the living, and for a small fee, I obtained their current home and e-mail addresses. Both of these good folks, I hoped, might well harbor simmering grudges against the firm.

Via text message, I suggested we get together at a café equidistant from our three domiciles, to discuss “a matter of mutual interest.” Vagueness was best. Let them think I wanted to start a new business, or something. Neither did I add, “for old time’s sake,” which would have been patently disingenuous, since, as colleagues, we had always hunkered down in the rich data of our separate projects. Within a few minutes, affirmative replies were forthcoming.

The next morning, at 10:30 sharp, we were ensconced at a corner table of the café, with baked goods and beverages of choice (hot, since it was February) in front of us. After minimal pleasantries, I opened the proceedings with a pre-prepared grabber: “I don’t know about you two, but the company doesn’t seem to have bothered to cancel my access.” Their startled expressions told me I already had them on the hook. Although neither had touched their food or drink, they were practically salivating with curiosity.

“This is how I know. At the end of my termination interview, the P.D. –a new one, possibly after your time– informed me that my password would be invalidated in one hour. It was true, I checked. But, the other day, for some reason, I decided to try an old password, which I had temporarily lost ten years ago. Apparently, they had neglected to cancel that one, since lo and behold, it still worked! Maybe, they had been careless because they assumed my big severance bonus would guarantee undying loyalty. Ha! And there’s more.”

By now, Roger Mott, a big, red-faced man who must have been approaching seventy, and who obviously loved his food, was frozen, open-mouthed, with his fork poised in midair, a piece of baba au rhum dangling precariously from a single tine.

“Of course, even if they had tried to take proper precautions, they would still have had security issues, things they couldn’t have guarded against. You know, it’s not like, when they canned us, they forced us to eat lotus blossoms, to make us forget how the statistical models worked. I mean, we were the ones who designed those models, and the ones who wielded them all those years to make the firm filthy rich! But look at it from their point of view. What were they supposed to do, trade in good models for new, inferior ones?” Estelle Saperstein, the third person at the table, and my immediate predecessor on the chopping block, was a tall, thin woman in her early seventies, about my age. Estelle had been a magna cum laude with a double degree in Math and Physics from someplace good –Stanford, I think. As I paused for effect, she was apparently unaware that she was stirring her latte with her right index finger. Either the latte was no longer hot, or she was.

Still cautiously, I nattered on. “Any hypothetical former employee still in possession of an active password, and who knew how to work the models, could either alter data in ways that severely reduced the firm’s profits or, if said person preferred, partake of their assets!” I suppressed an impulse to grin or to wink.

“But that password, Mr. Wolf,” objected hardheaded Estelle, “must only be operative in the company’s internal network. Your putative hacker would need access to the office computers. Didn’t they ask you to return your keys? Or do you have old keys, too?” When a serious woman like Estelle makes a lame joke like that, you can tell she is in the throes of some overwhelming passion –in this case, revenge and/or greed. I knew she was on board.

“Call me ‘Paul,’ please, Estelle. The old password works in my apartment, on my personal laptop.”

“Wow, a live p-word!” cried Roger Mott, flipping the piece of baba home. “I never even thought of trying mine.”

“Why should you have, Roger?” I replied. “An honest, loyal fellow like yourself? And I bet you’re so honest,” I said to Estelle, “that you never thought of trying yours, either. Besides, it doesn’t matter whether your passwords work. Mine does.” Estelle’s finger had stopped stirring her latte, but it was still extended, as if she were checking the wind.

“Which caper should it be?” asked Roger, devouring the rest of his pastry in two huge bites. “Rob them blind, or make the business crash?” He was obviously a zealot.

“Why does it have to be either-or?” asked Estelle mildly.

“O, ho! You took the words right out of my mouth,” I said, which was true. “But let’s drink up, before our beverages get cold.”

“May I propose a toast?” suggested Estelle, who now wore a loopy, myopic grin. “To larceny.”

“To grand larceny!” cried Roger.

We drank to that, and agreed to meet again, two days later, same time, same place, which Roger dubbed “the war room.” Meanwhile, I would set in motion the process of extracting company data. After I had paid the check, tip included, we shook hands and went our separate ways.

Let me underline the fact that, at each stage of my pitch, I had kept a weather eye out. If either of my co-terminate-ees had shown the faintest signs of panic or moral umbrage, I would have shut my pie hole fast, except for eating the apple pie I had ordered, which turned out to contain too much cinnamon, anyway.

In the event, I should have shut my P.H. Thirteen years later, this is no longer an option. So what! In for a dollar, in for … damnation! But that, as a witty college professor of mine once quipped, is “putting Descartes before Ho-race” (which he pronounced with a French accent, making it sound like “horse”).

I proceeded in logical order. To oversimplify, I would hardly have waited to rob the company until I had bankrupted them. Without getting too technical (since I assume the reader is not using this story as a sleeping pill), here are a few salient details. I should point out, in passing, that by the time the three of us reconvened, my larcenous maneuvers were already well under way. When I laid out the plan, far from demurring, Roger and Estelle seemed mesmerized.

Fleecing the Firm: Using pseudonyms, and what are called “margin accounts” (which basically means buying things with other people’s money), in the course of a few months, with credits from several brokerage houses, I made about 100 separate purchases of company stock, each between 50 and 300 shares. I then sold all the shares at their current price (high). A few months later, after I had caused the stock to plummet [see infra], I re-paid the brokers in re-purchased shares (low).

Need I add that these machinations involved unnumbered Swiss accounts? All told, I probably netted about 57.36 million dollars. “Probably”? “About”? These qualifications stem from the fact that the purloined amounts are stated in 2005-dollar values. Of course, being a man of my word, my own share was a paltry 19-plus.

The larceny entailed one further wrinkle. I transferred our profits to the banks through a tortuous trail of fictitious entities, so that anyone who smelled a rat would have had to bait the trap and chase the rodent for months, through places to which the chaser could not have gained access. If that sounds murky, it was. The best way to understand it is to think of money laundering, the sort of thing you have undoubtedly read about in connection with spy rings and drug cartels.

Timing, as I said, was crucial. Immediately after my final purchase, I began the demolition phase.

Deep-Sixing the Corporate Vessel: This phase was also carried out by means of a single process, which involved something called “float.” A bit more arcane than margin accounts, float is money set aside to meet anticipated claims. Normally (and don’t forget, Roger, Estelle, and I wrote the book), the firm would invest according to the size of estimated future claims, and their time frame: the shorter the time frame (called “short-tail float,” or STF), the more conservative the investments. My tactic now was to transfer a large percentage of the company’s STF into dubious instruments, such as junk bonds and penny stocks. For long-term float, or LTF, I transferred funds from the current, more speculative instruments into high-quality, low-yield bonds, mostly ten-to-thirty year Treasury notes.

How, you ask, was I able to hide these manipulations from the company’s current actuaries, not to mention its auditors? Dodging the latter, a highly competent bunch, was easy: I performed my statistical prestidigitations in the weeks right before the annual audit. And let me tell you, that audit was a sight to behold! More than half of it was in BOLDFACE CAPS!

The way I fooled the actuaries falls under the heading, “so technical as to be soporific.” (Caveat, lector! You can skip this paragraph.) As I just mentioned, my general strategy was to reverse the normal pattern of investments. The money transfers were made in the names of about thirty low-level company employees, and through a series of fictitious entities. By the time the actuaries could trace the paper trail, the damage had been done, apparently by the same people who cleaned their toilets and emptied their wastebaskets! A secondary pleasure was my knowledge that, when I was still with the Department, chicanery like this would have been detected almost immediately, and ruthlessly staunched.

Please note that the bear market in U.S. stocks did not begin until 2007, whereas my operations ended in mid-2006. In terms of the market collapse, I was a minnow, although, regrettably, the minnow’s revenge occasioned extensive collateral damage, such as the bankruptcy of several insurance companies, with the concomitant loss of thousands of jobs. To make my omelet, yes, I broke a lot of innocent eggs. For that, I am truly sorry, but those eggs will be happy to learn that I am about to undergo a severe, if belated, punishment.

It is time to explain the hints I have been dropping like breadcrumbs about the demise of my scheme. About three or four weeks ago, one of my co-conspirators defected. And this, thirteen years after having gratefully acknowledged the receipt of some nineteen million dollars! In true cowardly fashion, she (yes, Estelle) confessed her defection via text message. By resorting to this, the most impersonal and pusillanimous mode of communication, she avoided facing my wrath, face-to-face:

Estelle: hi p. scnd thghts 2 rsky cnt me out. srry e

For the text-illiterate: “Hi, Paul. Second thoughts. Too risky, count me out. Sorry, Estelle.”

“Too risky?” After thirteen years? To which circle of hell should such a disingenuous coward and ingrate be consigned? Too angry to argue, or even to reply, I realized I had a huge problem. Why had I ever thought I needed partners? I hate to admit it, but the reason may have been as simple as an old, newly unemployed man’s loneliness. Well, soon enough, I would have plenty of company –kindred souls, too.

I mulled my options:

1. Murder the woman in some cruel, Dantean fashion. Not me! Grand Larceny is one thing, but… I wonder if, aside from the heat of battle, Dante ever murdered anyone.

2. Try to buy her silence with an additional tranche from my ill-gotten gains. As I said, my principal motive had been revenge, not greed.

But before I could decide to bribe Estelle, another shoe –the second? third?– fell. A few days after her perfidious text message, a registered letter arrived from the New York State Attorney General’s Office, summoning me to appear before the Department of Financial Services, Insurance Division, at such-and-such an hour, such-and-such a date, in six weeks’ time. Although the letter outlined a complex process by which I could request a postponement, what would have been the point? Conceivably, of course, the summons could have been triggered by something I had done while I was at the firm. Sure! It could also have been sent by hackers from Mars.

Yesterday morning, I saw something that made it certain the summons was, indeed, related to my 2005 peculations. A small death notice in the Paper of Record told me that Estelle Saperstein had passed, at the age of 83 (a widow, without progeny). So much for bribing (or murdering) this woman! Presumably, her long-harbored remorse had led to an eleventh-hour decision to spill the beans, including chapter-and-verse of the M.O. I had outlined to her and Roger Mott at the café that fatal morning. Estelle had made a deathbed confession of my crimes.

A quick calculation told me that only two realistic options remained, federal prison or Dante.

Option One: I could spend my remaining days making license plates for twelve cents an hour.

Option Two: I could spend forever being torn limb from limb in the Second Ring of Circle Seven, the Violent Against Themselves.

This particular contrapasso is even more convoluted than most. As Dante learns from one of the damned, when a suicide’s soul flees his despised body, the body is flung into a wood, where it metamorphoses into a thicket, the leaves of which the Harpies eat, inflicting excruciating pain. Since the thicket is a perennial, of sorts, the torture is unending.

After Judgment Day, when the soul descends to re-claim its body, an even more exquisite wrinkle kicks in. (I know, I know, a mixed metaphor.)

…ma non pero ch’alcuna sen rivesta,
che non e giuasto aver cio ch’om si toglie.

Que le straschinermo, e per la mesta
selva seranno I nostril corpi appesi,
ciascuno al prun de l’ombra sua molesta. (Inf. 13.104-08)

…But it would be unjust were we again
to clad ourselves in the flesh looted from our own souls.

So here we shall drag it, and in this gloomy wood
will our bodies hang, each one
on the thorn bush of its painful soul.

Caro lettore [Dear Reader], which punishment would you have chosen? Prison, I assume. But, as always, I am more curious than prudent. So I will end this long account by noting that I am about to proceed to the bathroom, where, among my panoply of medicaments is a paracetamol compound reserved for just such an eventuality as this.

Don’t be shocked! Keep in mind that, were I to expire from natural causes in prison, I might meet the even more unspeakable fate of being consigned to the Ninth, and lowest, Circle, near the very bottom of which suffer those who betray their masters. But let’s not go there!


All Dante quotations are from The Inferno, Purgatorio or Paradiso (transl. Robert & Jean Hollander, Random House, Anchor Books, 2000, 2004, 2008). The author wishes to point out that his narrator provides his own translations, sometimes also deviating from the critical commentary of the Hollanders.

Technical details about re-insurance:


Berkshire-Hathaway Annual Report, 2017: www.berkshirehathaway.com/2017ar/2017ar.pdf

Please note that the company in this story is fictional, in no way modeled on either Berkshire-Hathaway’s reinsurance division, or any other actual entity.


Stories by Ron Singer have appeared in many publications., He is also the author of thirteen books, including Uhuru Revisited: Interviews with African Pro-Democracy Leaders (2015),which is available in about 100 libraries across the U.S., and beyond. For details, please visit www.ronsinger.net.

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