Bookkeepers

Book of Genesis

 

Big Tom was a gangster.

We didn’t know that. Being 11, maybe 12, what did we know?

To a suburban, white preteen in the early 1990s, a gangster was a twentysomething black guy in an Oakland Raiders hat being paid pennies on the dollar by exploitative record companies to preach the ghetto gospel on cassette tapes and CDs.

By the time we were high schoolers, we had a better idea about Big Tom, but even then, we didn’t get it. To the 16-year-old mind, gangsters look, dress and talk like Martin Scorsese characters. Big Tom looked, dressed and talked like the barrel-chested, uneducated redneck that he was.

We were all adults by the time David Chase and James Gandolfini introduced America to a more accurate — if a bit cartoonish — portrayal of a modern gangster who, not coincidentally, looked, dressed and talked almost exactly like Big Tom, only with an Italian accent instead of an east Tennessee drawl.

Big Tom was born in the projects which, in that little corner of Tennessee, are multiracial communities. A hillbilly who barely finished the 12th grade, he made his way in the world through hustle and muscle, not always (or even usually) in that order.

Right out of high school, he took a job driving a bread truck and used the money he made to bankroll the beginnings of what, two decades later, would be the city’s largest sports book. Along the way, he bought up local vending machine routes. The ones that weren’t for sale, he took. Then came rooming houses, car washes and a coin laundry he renamed in honor of his first granddaughter after our best friend accidentally got someone pregnant at 18.

To the five of us who spent more or less every other day hanging out with his youngest son, Big Tom was just our best friend’s father. I guess we knew he wasn’t like our fathers, or like anybody’s father for that matter, but it was only with the benefit of mid-twenties hindsight that we really understood: We’d spent half our childhood in very close proximity to the biggest reputed racketeer within a 200-mile radius.

A developmental psychiatrist might suggest that solves the mystery of my bifurcated personality — that the origin story for one half of my distinctively dichotomous psyche is a decade of unconscious assimilation.

On weekends, Big Tom spent virtually the entire day in his bedroom, watching football on two televisions and cursing at the players. During the work week, he’d get up hours before dawn to drive the bread truck, coming home just about the time we were all waking up on couches in the living room of the family’s modest split-level, where summer vacations were one long sleepover.

One day, he came up the stairs and casually told his wife — a second mother to us, even as our real mothers would all shudder at the suggestion — that he’d lost his job at the bakery. She looked up only briefly from the giant skillet of eggs she was stirring for a house full of 13-year-olds excited for another carefree summer day of driveway basketball and backyard pool hijinks. “Hmm,” she murmured, and went back to scrambling our brunch.

We never heard about the bakery again, and that didn’t seem strange to us. That the household breadwinner losing his job was a total nonevent. Barely worth a mention.

Everything

 

On November 18, 2025, Tarek Mansour, CEO of Kalshi, America’s leading prediction exchange, made a prediction of his own: His industry will become a trillion-dollar market sooner rather than later.

The California-born, Lebanese-raised Mansour started Kalshi (Arabic for “everything”) in 2018 with fellow MIT alum Luana Lopes Lara, a former ballerina who trained at The Bolshoi Theater School in Brazil, the only affiliate of Moscow’s famed Bolshoi Ballet Academy outside Russia.

Between them, Mansour and Lopes Lara boast stints at Citadel, Bridgewater and Goldman, the Holy Trinity of high finance. In a profile piece published earlier this year, Bloomberg called them “math nerds” bent on “giv[ing] Americans the inalienable right to bet on just about everything.”

“Everything” now includes sports betting, and that’s where the rubber meets to road — the point beyond which Mansour, Lopes Lara, Kalshi and a host of other prediction markets, including crypto-based exchanges, are in the eyes of critics no different from online sportsbooks like FanDuel and DraftKings. Or from your local bookie, for that matter.

Crypto.com which, like Kalshi, is regulated by the CFTC and authorized to offer “event contracts,” arguably gamed the agency’s self-certification process late last year to effectively create an overnight market for Super Bowl bets.

If you’re a designated contract market, the CFTC allows you to “list products for trading without prior approval” simply by submitting “a written self-certification” to the agency. That sounds reckless (it’s basically an honor system that asks exchanges to self-police), but the idea is to avoid unnecessary delays associated with a regulatory body mired in monotonous clerical work.

Under the protocol, exchanges are required to file self-certification submissions “no later than the close of business” the day before the next CFTC business day during which the contract goes live. For the Super Bowl contracts, Crytpo.com chose December 19, 2024. It was an ingenious move. Congress appeared headed for a shutdown the next day, and although a funding lapse was averted by an eleventh hour deal (then President Biden signed the bill on December 21), the mere prospect of a shutdown gave Crytpo.com an excuse to file into a pre-Christmas, post-election void.

As one attorney who spoke to Bloomberg for a feature piece in February put it, “They picked the timing pretty wisely.” Indeed they did, and Crypto.com also employed hilariously roundabout language to describe the contracts. They weren’t taking bets on the Super Bowl, they were merely allowing users to “express a market view related to the… economic and commercial impacts [of] an association’s final title event.”

As the same Bloomberg piece noted, it wasn’t until the contracts went live that the CFTC “realized the exchange had effectively walked through the front door and announced it would be offering a nationwide sportsbook.”

On January 14, the CFTC asked Crypto.com to suspend the contracts pending review, a request the exchange simply ignored, confident the incoming Trump administration’s affinity for disruption and allergy to regulation presaged a much friendlier environment for the sort of coup the exchange was attempting to orchestrate. Just a day earlier, an elated Mansour announced that Kalshi was adding Donald Trump Jr. as a “strategic advisor.”

Kalshi was already in the good graces of Trump world. In October of 2024, just weeks before the election, Mansour scored a major victory over the Biden CFTC, which sought to bar the site from offering election-related contracts. Then CFTC Chair Rostin Behnam complained that Kalshi’s contracts transformed the regulator into a de facto “election cop” and argued that the markets represented a threat to the integrity of the nation’s democracy.

The US Court of Appeals for the District of Columbia said the agency failed to make the case. “The Commission has not substantiated that risks to election integrity are likely to materialize if Kalshi is allowed to operate its exchange during the pendency of this appeal,” the court wrote, dissolving a stay on contracts allowing customers to bet on control of Congress.

Just hours after the ruling, the congressional contracts were live again and the site teased a new offering: Contracts on the outcome of the presidential election. Two days later, Mansour unveiled what he called “the biggest news in the history of prediction markets”: A contract to bet on the next occupant of The Oval Office.

Over the next four weeks, Kalshi took more than $120 million in bets on the outcome of the presidential election. The collective wisdom of those bettors had Donald Trump running more than 20ppt ahead of Kamala Harris, a “prediction” so starkly at odds with professional polls that Kalshi was lampooned in some corners.

The MAGAverse took notice. “Honestly, I think that chart’s about right,” JD Vance told comedian and podcaster Theo Von on October 22, 2024, when Trump’s odds on Kalshi were rising daily. “I think we’ve probably got about a 60% chance of winning.”

During his chat with Vance, Von said betting markets were a much better way to get a read on likely election outcomes. After all, he said, “It’s people putting their money down.”

The very next day, Fortune published a profile of Mansour who, when asked if Trump would win the election, subtly suggested the outcome was a foregone conclusion. “You don’t need to ask that question anymore,” he said. “That’s the whole point [of Kalshi]. People don’t lie with money.”

Shayne Coplan, the 27-year-old founder of Polymarket, the crypto-based prediction site which until very recently maintained a volume lead over Kalshi, makes the same argument: That between the conviction implied by a monetary wager and the wisdom of crowds, prediction markets are bound to be more accurate than traditional polls, to say nothing of any one individual “expert.”

“As price-discovery theory would go, a ton of clueless people trading would be more predictive and accurate than one expert,” Coplan told The New Yorker‘s Kyle Chayka, for a piece published the same day as Mansour’s 2024 Fortune profile.

Polymarket was technically illegal in the US. In 2022, the CFTC dropped the hammer, accusing the site of peddling unregistered swaps. Rather than fight the government, Polymarket paid a $1.4 million fine and barred US users. For US-based bettors with a VPN and a crypto wallet, the ostensible ban was no obstacle, but it did raise questions about the extent to which 2024 election bets might naturally “skew toward certain demographics: Non-American, male and extremely online,” as Chayka put it.

In the two months leading into the ballot, there was widespread speculation that Polymarket’s presidential election odds were being gamed by a consortium of whales in a roundabout conspiracy to influence the vote. “One possibility… is that [large bettors are] intentionally manipulating the market to create the perception of swelling momentum for Trump,” the FT said at the time, noting that the theory was “made more compelling” by Trump World’s penchant for citing Polymarket odds “as incontrovertible proof that a Trump landslide” was in the offing.

On October 6, for example, Elon Musk jumped at the opportunity to amplify the moment when Trump pulled ahead of Harris on Polymarket. “Trump now leading Kamala by 3% in betting markets,” Musk wrote, in a post viewed more than 87 million times. Those odds, Musk said, are “more accurate than polls, as actual money is on the line.”

Three weeks later, on October 27, Musk used similarly deterministic language in predicting a landslide for Trump “as foretold in the prophecy,” a reference to Kalshi odds which were peaking near 70%.

Although it was indeed “easy to imagine Musk and fellow influential Trump supporters creating a feedback loop that directs followers to the prediction markets then cites them as a measure of the campaign’s momentum,” as the FT put it, Coplan dismissed the notion seemingly out of hand. “[The bet] resolves to the outcome of the event — that doesn’t necessarily mean it has bearing on it,” he told The New Yorker.

By Election Day, Kalshi had the race much closer, but Trump’s win (and the “red wave” more generally) served as a kind of propaganda coup for betting markets. They were right, directionally at least, and that was a big deal.

“The pollsters got it wrong. The pundits got it wrong. The press got it wrong,” Kalshi crowed, the day after the election. In the same social media post, Kalshi quoted a 100-year-old article in The New York Times: “As the NYT wrote one century ago, ‘[Election] betting odds are ‘never wrong.'”

There was something a bit disingenuous — or at least sly — about the reference. Although the Times article (which ironically described a slow down in betting activity ahead of the 1924 election) did indeed testify to the wisdom of crowds placing monetary wagers on elections (which was common prior to 1940), the verbatim excerpt read as follows: “It is an old axiom in the financial district that Wall Street betting odds are ‘never wrong.'”

It’s a subtle difference, and while Kalshi didn’t technically misquote the Times, the reference felt like an attempt to validate the company’s business by way of age old wisdom as conveyed by America’s paper of record.

Never mind the rich irony in citing an organ of the establishment to credential an anti-establishment platform. The implication itself wasn’t, strictly speaking, accurate. The Times didn’t say betting markets were always right. The paper merely quoted a pithy, self-congratulatory dictum on Wall Street, where financiers of the day were convinced that the balance of monetary wagers was “never wrong.”

While Kalshi’s “X” account was busy quoting 100-year-old, archived articles from the Times, Mansour was marveling at the popularity of the company’s app which, on the eve of the election, held the top spot in Apple’s App Store, having leapfrogged ChatGPT, Instagram and TikTok.

In the lead-up to the vote, Google search interest for Kalshi was simply off the charts.

A Wired article published three hours after the company’s celebratory “X” post recounted the mood at Kalshi, where “staff [were] ecstatic” as they “followed the startup’s climb up Google Trends.”

“We overtook everything,” Mansour said. “Even Pornhub.”

Another golden age

 

“We are beyond excited,” Mansour enthused, on January 13, 2025, calling the tie-up with Trump’s eldest child “a major milestone” for the company “and for how Americans uncover the truth in [an] often biased media landscape.”

The very next week, Kalshi used the same CFTC self-certification process Crytpo.com used a month earlier to begin offering its own sports contracts, which Mansour described as “legal sports markets, accessible to Americans in all 50 states.” “The Golden Age of markets is here,” Kalshi’s official social media account exclaimed, parroting the “golden age” proclamation from Trump’s second inaugural address delivered three days previous.

Kalshi’s been running sports-related event contracts ever since, even as their legality remains contentious particularly at the state level, where officials in Maryland, New Jersey and Nevada (for example) argue Kalshi’s wittingly flouting state gaming regulations.

As Maryland’s Lottery and Gaming Director put it in April, after Kalshi took more than half a billion in action on March Madness, accounting for more than 15% of all legal wagers on the tournament, “They’re conducting sports wagering without a license and in doing so, they’re avoiding the collection of sports wagering taxes that legal operators pay to the State.”

Maryland’s one of several states to hit Kalshi with a cease and desist order. Maryland’s letter is typical of the demands: It accuses the company of “offering what is, in fact, wagering on sports events [without] holding a sports wagering license.”

For its part, Kalshi says the Commodities Exchange Act — the relevant federal statute under which the company’s allowed to list CFTC-regulated event contracts — supersedes state law, consistent with the Constitution’s Supremacy Clause, which provides that federal law is “the supreme Law of the Land.” As a government primer published by Congress notes, that language “is the foundation for the doctrine of federal preemption, according to which federal law supersedes conflicting state laws.”

Kalshi relies on preemption to make the case that its sports contracts are legal in every state. The instruments are regulated by the CFTC under a federal statute, and that’s the end of that. Or at least that’s how Mansour sees things. At an April event in San Francisco, he was brash. “We’re not necessarily very concerned” about cease and desist letters “because we are regulated at the federal level,” he said. “State law doesn’t really apply.”

Kalshi was aggressive out of the gate, asking courts in Maryland, New Jersey and Nevada for an injunction blocking the states from any attempt to meddle with the site’s event contracts. Initially, that effort was successful in Nevada — where a judge agreed that state regulators “have no jurisdiction to decide that Kalshi’s conduct violates state law where, at least at present, those activities are legal under federal law” — and in New Jersey — where a court, citing the Nevada decision, said Kalshi’s sports-related event contracts “evidence by their very existence the CFTC’s exercise of its discretion and implicit decision to permit them” on the way to agreeing with Kalshi that if the state were allowed to proceed with enforcement action, the company would suffer irreparable “harms to its reputation and goodwill.”

Kalshi suffered its first setback in August, when a judge in Maryland declined to enjoin the state from taking action against the sports-related contracts. In that opinion, judge Adam Abelson delineated between three types of preemption. In arguing that so-called “field preemption” inoculates Kalshi’s sports contracts from state intervention, the company asserted that when Congress “expand[ed] the Commodities Exchange Act to cover swaps traded on designated contract markets, [the federal government] has occupied that ‘field’ such that when online sports wagers are offered by a company like Kalshi, as opposed to by online sportsbooks like FanDuel or DraftKings, they need not comply with state gaming laws.”

Viewed in that light, Kalshi’s argument seems less than compelling, to put it politely. As Abelson went on to point out, there’s “a strong presumption” against field preemption, and because “the courts and Congress have long recognized states’ authority to regulate gambling conducted within their borders,” that  presumption applies to this case.

The court conceded that Congress “had some field-preemptive intent when it enacted the CEA” but Abelson, stating what to me seems obvious, said it’s not clear “the ‘field’ that Congress intended to ‘occupy’ included gambling.” Kalshi, the judge went on, needs to prove “that Congress clearly and manifestly intended to strip states of their authority to regulate gambling if the company offering such wagering opportunities has been approved to sponsor a designated contracts market for commodities trading.”

And so it was that Kalshi was 2-1, in sports parlance. Two early wins (in Nevada and New Jersey) and one loss (in Maryland). Everyone appealed.

Fast forward to November and the same Nevada judge — Andrew Gordon — who granted Kalshi the original injunction reversed himself. “I will tell you, in all candor, I’m leaning toward dissolving the injunction,” he told Kalshi’s lawyers, at a hearing on November 14.

Gordon, who a month earlier declined to grant Crypto.com a similar injunction to the one he gave Kalshi in April, marveled at the audacity of Kalshi’s implicit claim. “[Y]our definition is so broad that pretty much anything can become a swap,” he said, on the way to chiding Kalshi in abrasive language.

It took the “brilliant people at Kalshi” to divine that sports bets are actually commodities, Gordon sneered, before alluding to the logic from the Maryland decision in calling it “absurd” that Congress intended to grant sites like Kalshi a license to run “nationwide gambling venues on any topic under the sun.” A few days later, on November 25, Gordon lifted his injunction, in the process “shattering prediction markets’ favorite [legal] theory,” as CoinDesk put it.

“Kalshi relies on a strained reading of the already convoluted Commodities Exchange Act in an attempt to evade state regulation,” Gordon wrote, in what he surely recognized will be viewed by the nascent prediction market industry as a watershed opinion. “Kalshi’s interpretation would require all sports betting across the country to come within the jurisdiction of the CFTC rather than the states and Indian tribes upset[ting] decades of federalism regarding gaming regulation, contrary to Congress’ intent.”

Citing his own ruling in the October Crypto.com opinion, Gordon reiterated that, “Event contracts that turn on the outcomes of sporting events are not swaps and thus do not fall within the CFTC’s exclusive jurisdiction.”

In a separate, but closely related, ruling issued the same day, Gordon declined to grant Robinhood, which partners with Kalshi, a restraining order against Nevada’s gaming regulators.

Robinhood began offering users access to Kalshi’s sports contracts in March, but pulled them after receiving a cease and desist letter from Nevada’s Gaming Control Board. Then, in August, Robinhood restored access to the contracts for its Nevada customers and promptly sued state regulators, echoing Kalshi’s claims that the contracts are regulated by the CFTC and therefore state law doesn’t apply.

In denying the site’s bit for a restraining order, Gordon noted that at the CFTC’s direction, futures commission merchants like Robinhood were required to warn customers about ongoing litigation related to the sports contracts and the risks associated with “various” legal proceedings. Robinhood’s customers, he wrote, were thus “on notice that the legal landscape under which Kalshi and Robinhood have been operating could change depending on court rulings.” Robinhood’s customers were dabbling in the sports contracts “at their own risk” not unlike Robinhood and Kalshi themselves.

And just like that, the same judge who handed Kalshi its first legal win dealt the company its most consequential defeat.

A sporting chance

 

When Robinhood CEO Vlad Tenev addressed a crowd gathered in September for the company’s annual summit at the Grand Prix Plaza in Las Vegas, the awkward, apologetic persona who suffered through a congressional interrogation during the GameStop fiasco in 2021 was gone. In its place was a showboating self-promoter dressed as a race car driver. Trading on Robinhood, he told the audience, is “one of the most intense lifestyles out there.”

In a piece documenting the spectacle, The Wall Street Journal described Tenev as a “cult hero” to Robinhood’s most dedicated users. “Few people,” Hannah Erin Lang wrote, have “done more to stoke” risk-taking among individual investors than Tenev, whose app “makes it easy not just to buy and sell ordinary stocks, but to invest in options, cryptocurrencies and other exotic financial products, even to make sports bets.”

The Journal‘s profile describes a kind of cultural revolution at Robinhood where Tenev, who once assured US lawmakers that nearly all of the company’s users were long-term investors, now directs his team to stay laser-focused on clients who trade riskier products like options and crypto, which the app depends on for most of its revenue.

Tenev likewise abandoned any pretense to decorum in his personal life. “I said, ‘Wait a minute, why do I care what other people perceive [about] the CEO of Robinhood?'” he told Erin Lang, describing the thinking behind a decision to ditch his trusty Tesla Model 3 for a collection of high-end classic cars, including a 1970 Lamborghini.

Prediction markets are Robinhood’s fastest-growing business. More than a million of Tenev’s customers have traded nine billion contracts over the life of the company’s partnership with Kalshi, and now he wants more. The company this month announced plans to launch a futures and derivatives exchange in conjunction with Susquehanna. The venture’s aimed specifically at “building on strong customer demand for prediction markets,” as Robinhood’s General Manager of Futures put it.

Three weeks after Tenev regaled the Robinhood faithful in Vegas, Kalshi finally topped its Election Day 2024 volume record. On Saturday, September 27, 2025, the site saw $260 million in action and $275 million more that Sunday. According to an industry website, 90% of that weekend’s volume was “related to football” and 98% involved sports contracts of some kind.

Late last month, InGame published a detailed analysis covering “every trade” reported by Kalshi from February 25 to May 17. The figure below, based on that data, gives you a sense of how quickly sports came to dominate Kalshi’s business in the months after it launched its first sports-related contracts.

As the editorial accompanying InGame’s analysis put it (emphasis mine), “the growth of sports trades over that period [is] even more stark” than the overall volume of such activity. At one point in April, sports contract activity comprised 76% of the running total. A month later, that figure was still north of 70%.

“Over the first 21 days of the sample, sports made up only around a tenth of trading volume,” Daniel O’Boyle, a veteran of the London Evening Standard who’s covered gambling for half a dozen years, wrote. “But from March 18 — the first full day in which Kalshi’s single-game March Madness markets opened — onward, sports have dominated.”

Fast forward six months, and the numbers are even more lopsided. In the trailing seven-day period which included Thanksgiving and Black Friday, an estimated 94% of Kalshi’s volume was sports-related. “As much as Kalshi tries to position itself as the place to trade on current events, sports continue to do nearly all of the heavy lifting,” Eric Ramsey, a data and policy analyst covering regulated US gambling, said.

In the same InGame analysis mentioned above, O’Boyle noted that because of Kalshi’s fee structure, it’s likely that the site “makes a larger percentage of its money from sports than DraftKings or FanDuel, businesses that are almost synonymous with sports betting in the US.”

Through Thanksgiving, shares of DraftKings and Fanduel parent Flutter Entertainment were down 9% and 18% for 2025, respectively.

American greed

 

On November 25, Polymarket officially announced its return to the US.

The CFTC will allow US users to trade Polymarket’s contracts on an intermediated basis, which is to say through licensed Futures Commission Merchants for futures and swaps.

Polymarket’s triumphant homecoming was made possible by the acquisition of a CFTC-licensed derivatives exchange and its affiliated clearinghouse for $112 million on July 21. Just a week earlier, Pam Bondi’s Justice Department dropped an investigation into the site.

Coplan, whose Soho penthouse was raided by the FBI shortly after the 2024 election, last month became the youngest-ever self-made billionaire on Bloomberg’s index of the world’s richest after securing a $2 billion investment from NYSE owner ICE.

“People rely on Polymarket because we provide clarity where there is confusion and accountability where there is ambiguity,” Coplan declared, in the press release announcing Polymarket’s US return. “We’re grateful for the constructive engagement with the CFTC and look forward to continuing to demonstrate leadership as a regulated US exchange,” he added.

This month’s adverse ruling for Kalshi in Nevada further complicates an already messy legal fight over the status of the site’s sports contracts. All high-minded rhetoric about the many virtues of prediction markets aside, the unavoidable reality is that financial prospects for companies operating in the space will turn heavily on sports betting — or sports “predicting” or sports “opining” or whatever euphemism you prefer.

Ultimately, the case will almost surely end up before the Supreme Court which first struck down a federal prohibition on sports betting in 2018. As one attorney told Bloomberg Law this month, of the Kalshi melee, “Whoever loses in the courts of appeal will file cert.”

By the time the high court agrees to hear the case (assuming they do), there’ll likely be another player in the prediction market arena. On October 28, former GOP congressman Devin Nunes, speaking in his capacity as CEO of Trump Media, announced that TruthSocial will soon host prediction markets through an exclusive arrangement with Crypto.com.

The family business

 

When we were 15, Big Tom bought a nicer, all-brick home a few streets over in the same neighborhood. It had a proper pool area with a small grotto feature and one of those built-in spillover hot tubs, which we obviously loved.

The downstairs had a sunroom, a den, a formal dining area and two sitting rooms, one of which was piled knee-high with pallets of candy and snacks for the vending machines. Upstairs, in an expansive master suite, Big Tom had small TVs placed one beside the other on drawer dressers lining the walls. This was years before mass market flat screens, and the PC revolution was in its infancy. On Saturdays and Sundays he’d pace around the room in circles, and the house phone rang every couple of minutes.

We were old enough by then to identify some of the men who stopped by to see Big Tom during the week. They were people we’d seen on the local news and when his wife greeted them we recognized their names from campaign yard signs  — every third person was “commissioner” of something or hoping to be. The rest were detectives and, in some cases, uniformed beat cops who always looked embarrassed and sheepish.

Once high school was over, everyone else stopped hanging out at Big Tom’s, but I kept up appearances. When he and his wife weren’t raising me, two university professors were, so to me, college wasn’t the immersive new adventure it was to everybody else. The course work was child’s play and campus life was nothing new. By the time I actually enrolled, I’d spent more time on college campuses than most professors.

Big Tom was determined that his son was going to take some financial responsibility for the child he had on the way, but a real job was out of the question for a list of reasons too long to enumerate here. And so, he started making collections for his father. I’d go along, and there we were, just seven years removed from the innocence of summer vacation sleepovers, collecting for Big Tom in his wife’s champagne-colored DeVille.

A year or so later, between my freshman and sophomore year of undergraduate school, I moved to the beach island where my real family vacationed during the summer. After that, I transferred to a major state school in a city far larger than, but not too far away from, the town where I grew up.

While I was in grad school, Big Tom did a short prison bid for federal bank fraud, conspiracy and perjury. The next time I saw him I was 28. He’d moved again by then, this time to a 5,000 square foot monstrosity on a couple of wooded acres. The small-town rumor mill said he outbid a local celebrity basketball coach for the place.

I pulled up, got out, walked in an unlocked front door and weaved through hallways until I found a kitchen where Big Tom’s wife was milling around. I knocked on a wall: “Guess who?” Not even a little startled, she turned and smiled, registering nothing like the surprise you’d expect from someone you hadn’t seen in nearly a decade.

There I was, a grown man with two college degrees and 10 years of adult life experience, but she still saw the precocious kid whose homework revisions saved her youngest son from failing every grade from the sixth on up. And who might’ve inherited the family business if he hadn’t skipped town for bigger, if not always better, things.

“I’m back in town for a while. I’m gonna grab a quick MBA here,” I told her, describing a Master’s degree in business precisely as it deserved to be described: Like something of no consequence you pick up on a whim because circumstances make it convenient or expedient. “Hmm,” she murmured.

My friend was out, and she didn’t know when he’d be back. “I can try to call him, but–” she offered. “Nah, that’s ok. I’ll just hang out a while, maybe I’ll catch him. Where’s Tommy?” She pointed upstairs and I remembered it was Sunday. “Games on?” She nodded and offered me a peanut butter sandwich. The 12-year-old in me was happy about that. I had two.


 

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3 thoughts on “Bookkeepers

  1. Fantastic “deep dive”. As I was reading this, I was somewhat outraged that Congress hasn’t passed a law to clarify if this is legal and if so, what are the rules and regulations?
    By the time I finished reading, however, I was thinking “a fool and his money are soon parted”! If people want to gamble- they should be free to do so. Furthermore, even if it were illegal, there would still be ways to gamble.
    Trump, and his family, are enriching themselves tremendously. Using unelected appointees to help enrich him- exactly what he pretended to be outraged over by Biden. It will be interesting to compare their net worth on January 1, 2025 to January 1, 2029.
    This is not for me! I was the other type of “bookkeeper”, however. I restrict my “gambling” to US equities.

  2. I got a heads up on this a couple months ago from a friend in a start-up that is trying to market-make for contracts on these sorts of “exchanges”. Environment sounded like the wild west. Also it’s not clear to me that there is much benefit to society since the priority doesn’t seem to be on representing risks that someone might need a legitimate hedge for.

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