In 1865, a failed stockbroker tries to pull off one of the boldest financial schemes in American history: the original big short.

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This story was published in collaboration with The Boston Globe.

Midnight, April 2, 1865

It had been a long Saturday night for James Fisk Jr. His unkempt blond hair marked the hours he had been running his hands through it, while his waffle-weave suit struggled to hold in his girth. Bones of Fisk’s food of choice — turkey — were strewn about. As the clock rounded midnight, and Fisk rattled his many rings against the desk, he started to wonder whether tonight was the night. Maybe he should have just had a good sleep and come to the telegraph office in the morning.

But for Fisk, stockbroker and financial schemer, every minute, every second, counted. Had he stayed at home, he would have paced the night away. He might as well camp out at this Boston office of the American Telegraph Company. At any moment, in those predawn Sunday hours, he anticipated an end for General Robert E. Lee’s Confederate Army of Northern Virginia. Each puff of Fisk’s cigar brought him closer to it, so he hoped.

Nearly 500 miles to the south in Washington, D.C., President Abraham Lincoln anxiously waited at the War Department for the same news. Slumped in a chair, his linen jacket hanging off his wiry frame, Lincoln loomed large in the small room at the Winder Building on 17th Street. Next to Lincoln sat a stick he carried at the urging of his wife, Mary Todd, protection against a possible assault. Lincoln’s presence in the room originally came from necessity — he could get work done there. The White House next door had become overrun by party dignitaries, office seekers, and lingerers.

Lincoln had come to know the telegraph operators and cipher breakers stationed at desks around the room, and had made it a habit to flip through new messages. When he finished reading through a pile, he seemed to always have a sarcastic comment ready to elicit a chuckle from the room.

Lincoln and Fisk’s interest in the events in and around Petersburg, Virginia, early that morning could not be farther apart. Where Lincoln saw the last gasp of an insurrection that had cost some 750,000 lives and paved the way to a more perfect union free of the national sin of slavery, Fisk saw dollar signs. Lots of them.

As the sun crept into the Sunday sky outside the telegraph office, Fisk wondered if his excitement was premature. Then it happened. The office roared to life. The wires sputtered with fragments of news. The Confederate forces could not hold off the Union juggernaut of General Ulysses S. Grant. Casualties and desertion had taken their toll on the Army of Northern Virginia and now a Union force in the predawn hours of Sunday, April 2, had punched a hole in the wafer-thin line.

Wartime protocols meant military messages took priority on the wires. But rules had never stopped Fisk before. He bribed the telegraph officer to send out a message in between the clacking of military wires. The destination: Halifiax: Nova Scotia. The message: “Go!”

With one word, James Fisk unleashed one of the greatest financial schemes in American history.

Weeks before Fisk held vigil at the telegraph office, he sat on a train to Boston, watching the scenery of New York City recede out the window. He had come to New York brimming with plans to strike it rich. Instead, over the past six months, the Street had eaten him alive.

Fisk had wooed clients with booze to persuade them to let him invest their money in stocks and bonds. But before he knew it, Fisk was caught in a bear market. As he pumped money into the black hole of speculations, his losses mounted. He was one of the many casualties of Civil War Wall Street, with outcomes on battlefields as far away as Mississippi sending the stock market and gold prices on wild, unpredictable swings. Fisk was busted, but vowed to be back. “Wall Street has ruined me,” he proclaimed, “and Wall Street shall pay for it.”

To Fisk, there were business opportunities everywhere, even on this train to Boston in March 1865. A traveling companion shared with Fisk his tale of financial woe, and happened to mention a textile patient that he was desperate to sell. In between station stops Fisk figured out how to broker that transaction — for a modest fee, of course.

Six or seven hours on the train provided Fisk with the perfect chance to concoct his next gambit, which would turn out to be his riskiest to date. Opening a New York City newspaper, he scanned to the financial news coming in from London. “The market in government securities is firm” was a phrase Fisk had grown all too familiar reading. Fisk couldn’t help but notice listings in London for Confederate bonds. Where some patriotic Northerners saw a source of derision, Fisk saw opportunity: He wanted to short the bonds of the Confederate States of America.

The plan was simple. In order to short a bond, Fisk would need to borrow that particular issue from a broker, point A in the transaction timeline, and sell it to another party. At some future date, he would need to “close” the short, which involved purchasing the bond at the new market price — point B — and returning it to the broker. The difference in price between point A and point B is what Fisk would pocket, and the short the bond is to bet on that price dropping. If the bond rose in value, Fisk would owe his shirt to the broker. But if the bond’s value plummeted, he could strike it rich.

Fisk had set his sights on something big — in fact it couldn’t get much bigger. He wanted to short Confederate bonds to the shrewdest financial minds of London, the commercial capital of the world. To pull that off, Fisk needed to know just one thing: the outcome of the Civil War before anyone else.

The idea of exploiting privileged information for financial gain using technology was something that would have crossed Fisk’s transom earlier in the Civil War. Western Union employees, for example, had allegedly made a fortune in the gold markets by leveraging their advance knowledge of war news in the first months of the conflict.

Confederate war bonds had been trading in London since 1863, at times nearly at par, or face value. By the early months of 1865, the bonds could be purchased for some 35 cents on the dollar. Fisk knew that once the Confederacy was toppled and word spread, the price of the bonds would plummet even further — probably to mere cents on the dollar. An investor in the right positions if that happened could earn a fortune.

And that fortune was Fisk’s target. A moving target. Even with all that had to go right on the trading front, the transactions were, relatively speaking, the easy part.

First, Fisk had to know the moment the war ended, which required being stateside. Then, at roughly the same time, he somehow had to be inside the London financial world with the information and with enough time to spare to buy up vast quantities of Confederate bonds, sell them, and then buy them back at the lower price to close the short. And he had to do it all before anyone else in England knew the war was over. If word of the war’s outcome hit the London street before he could complete the scheme and get out clean, Fisk wouldn’t just lose everything, he’d drown in debt for the rest of his natural life.

One other thing: The trans-Atlantic telegraph system that connected the United States and England was down, and with it the only way that existed to transmit information between the countries in real time.

Pulling off his scheme sounded about as plausible as the plot of Jules Verne’s new novel, From the Earth to the Moon, in which men climbed in a cannon and were launched to the moon. But that wasn’t about to stop James Fisk.

Fisk needed to assemble a team like none other. As soon as he settled back in Boston, he tracked down some old friends. Years before, while working as a traveling salesman around New England, Fisk had become known as the “prince of peddlers.” He caught the eye of Boston merchant Eben Jordan, who hired him for Jordan Marsh & Co., the department store he had cofounded some two decades earlier. Fisk negotiated legitimate military contracts for the firm in the war’s early years before he struck out for his ill-fated Wall Street debacle. But he’d left Jordan Marsh with a stack of contacts in and around the moneyed classes of Boston that would prove invaluable in the scheme that was to come.

For his London plot, Fisk needed capital — lots of it. He couldn’t go to just any investor. His targets couldn’t be old Brahmin money. No, the likes of hoary brokerage Lee, Higginson & Co. would not put their necks on the line for such a wild venture. Instead, he needed nimble trailblazers with deep pockets and preferably questionable morals. Disciples of Andrew Dexter Jr. could certainly fit the bill. The financier embezzled and laundered funds by creating fake banks and circulating far too many notes even for the legitimate banks he owned in the American West. Another prototype to court was Sarah Howe, who knew how to exploit the well-heeled, adventurous women of Boston. Fisk went into full salesman mode, initiating three investors into his secret circle. He knew enough to only tell his draftees what they had to know and to leave no paper trail.

Next, he needed to recruit another pair of arms and legs on the ground in London — Fisk couldn’t be in two places at once. Someone who could keep his mouth shut and could think on his feet almost as quickly as Fisk did. That person came in the form of a broker named Hargreaves, whose role Fisk kept under wraps so successfully that no one would ever learn more than his last name.

It was no accident that Fisk’s machinations always came wrapped with a certain amount of flair. The son of a salesmen, he was born in Vermont on April Fools’ Day 1835. At 15, Fisk joined Van Amberg’s Mammoth Circus and Menagerie for a three-year stint. For the rest of his life, Fisk would infuse his enterprises with the showmanship of a carnival barker. Getting ahead in life meant pulling the wool over people’s eyes while they welcomed the experience.

Fisk had learned a big lesson from a scheme that he had run earlier in the Civil War: Don’t just plan for success, but account for what would be lost if it were to go wrong. With cotton scarce in the North in that first flush of war, Fisk had brazenly smuggled cotton across military lines. He garnered great returns, at times pulling more than $800,000 worth of the contraband crop out of the South. That only fueled his appetite for more, even if it meant risking his own life — he once barely escaped a Confederate patrol.

Fisk also used agents spanning Southern ports occupied by Union forces and the Mississippi River. These operatives were loyal and included the likes of famous actress Lotty Hough.

Fisk’s father, who had passed on his salesman’s hustle to his son, served as one of his son’s cotton agents in Tennessee. James Fisk Sr. had a reckless streak in him from his own peddling days. “I don’t think Father would tell a lie for twelve and one-half cents,” Fisk once reflected, “though he might tell eight of ’em for a dollar.” While hustling for his son’s scheme, Fisk Sr. came down with sunstroke from the long hours under the hot Southern sun. He never fully recovered. Fisk Sr. was stretchered with ice packs attached to his body back to Vermont, where he would spend the rest of his days in an asylum.

The average person would have sworn off get-rich-quick schemes. The average person might have tried to make amends with family and maybe with God. Fisk wasn’t average. Faced with his father in an asylum, Fisk toyed with using his know-how to fund a few charitable hospitals to tend to the North’s mounting wounded, though the idea was short-lived. Fisk’s enduring lesson instead? He had to scheme better and bigger.

As Fisk gathered his four-person squad for his London conspiracy — as maps, diagrams, bond price trends, London broker directories, and ledgers put together a road map to easy street — this big short would be his masterstroke, his redemption for past slip-ups, and his glorious legacy.

Telegraph lines had previously connected Ireland to England and onto continental Europe, bringing people, governments, and markets into near-instantaneous contact for the first time in history. But by the 1850s the biggest project for the international economy was yet to come: a cable that would link the emerging hub of New York to the established financial powerhouse of London.

Relying on five American financiers and the support of the British and American governments, the 2,500-mile trans-Atlantic cable was laid by the USS Niagara and HMS Agamemnon in the summer of 1858. Despite heavy seas and three botched attempts to get the initial line started, the first message zipped across the Atlantic in mid-August, from Trinity Bay, Newfoundland, to Knightstown, Ireland: “Europe and America are united by telegraphic communication. Glory to God in the highest, on earth peace, goodwill towards men.”

On September 1, 1858, a massive parade made its way down Broadway in New York City to herald the success. Some 100,000 spectators (out of the city’s 600,000) looked on as one of the project’s chief architects, Cyrus Field, led a procession. Field, sailors from the Niagara, and dignitaries marked the occasion that celebrated the ability to transfer news — including of the valuable financial sort — in a matter of minutes, rather than days or weeks. This technological feat could alter financial markets forever.

But on the day of the parade, the first iteration of the trans-Atlantic cable breathed its last. What was initially viewed as a glitch led to garbled messages, missed communiqués, and then finally lost communication. Nobody knew why, but the cable had broken. Some theorized the sun exposure on the decks of British and American naval ships weakened the cable, as did repeated spooling and unspooling of the line.

The Civil War prevented the cable from being repaired. Financial markets returned to their old ways, waiting for steamships to cross the Atlantic with “breaking” news that actually would be more than a week old. With the cable broken, word took approximately 10 days to reach London from New York. This was the key to Fisk’s plot. When the Confederacy crumbled, London would be 10 days behind.

In the pre-telegraph era, an array of schemes had been tried to beat out competitors for financial information. In the United States, “optical telegraphs” sent coded message via signs from hilltop to hilltop that transmitted information faster than someone on horse. Some financial firms even implemented carrier pigeons.

By the time of the American Civil War, newspapers and financial institutions alike had deep-water boats to meet trans-Atlantic steamers. From these vessels, they would flash optical signals to shore regarding financial news and other information. For a fee, anyone could get in on it.

For Fisk to carry his plan to fruition, he had to come up with an end around to all of these methods, and beat everyone else on two continents to the punch. He decided that some kind of vessel — and a fast one at that — would have to race across the Atlantic at just the right time.

One new type of sea vessel could actually travel completely unseen: The submarine. The United States Navy only had one submarine during the Civil War — the USS Alligator — which came into service in the spring of 1862 and was even observed in action by President Lincoln. But while being towed toward Charleston, she and her tugboat encountered bad weather and the Alligator foundered off of Cape Hatteras. On the Confederate side, the H. L. Hunley submarine, or “fish boat” as it was sometimes called, sank twice while undertaking sea trials — each time killing everyone aboard — and was twice pressed back into service. On the night of February 17, 1864, the Hunley attached an explosive to the side of the USS Housatonic. The mine detonated prematurely and the aftershock led to the Hunley going down with all souls aboard, never to be deployed again.

The cutting-edge submarines might appeal to the flashy Fisk, but even he could recognize that a sleek and traditional steamship would be the safest bet. A steamer of the sort they needed would run Fisk’s team at least $2,000. They’d need a captain and as small a crew as possible, all of whom would be kept in the dark about the scheme. Only Fisk’s right-hand man, Hargreaves, would know the real mission.

Logistics arranged, Fisk dispatched his new steamer to bring Hargreaves from America to Halifax at once to await further word. Halifax was the last major port on the North Atlantic before traveling to Europe, and one of the points on the existing telegraph lines farthest from the States.

All of which brought Fisk to his all-night vigil at the telegraph office in Boston on Saturday, April 1, 1865, waiting for the South’s demise. It was all too perfect. Fisk’s tour de force would commence on what was both his 30th birthday and April Fools’ Day, a day when only a mastermind could hoax a world on the lookout for hoaxes.

Union forces had advanced on the overwhelmed Confederate forces earlier that day, virtually cutting off the last rail link into Petersburg. That city was key — it was the last line of defense between the Union Army and the Confederate capital of Richmond, Virginia. It was only a matter of time before Grant broke through Lee’s lines. Fisk watched the clock and the wires.

On the Petersburg front lines, Brigadier General Lewis Grant’s ears were still ringing. Union artillery had kept up a bombardment of Confederate positions for over four hours. The 150 guns had unleashed their cannonade until nearly 2 a.m. on Sunday, April 2. The soldiers of the First Vermont Brigade had been laying on the ground, in the dark, for over four hours less than 600 yards from the main Confederate line. Now, two hours later, the Union assault was to begin. At 4:40 a.m., a signal gun from Fort Fisher ordered the assault forward and Union soldiers rose up to take on the thin Confederate line.

It was this initial assault in the predawn hours that led to a breakthrough of Union forces, the news that Fisk eagerly received in Boston. How delicious, worthy of a patented Fisk wry grin, that it was a regiment from his home state of Vermont that had played a key role in what could bring Fisk the glory he’d always believed he deserved.

In the early dawn of Sunday, Confederate garrisons and fortified positions tumbled like dominoes. By the late morning, word had been sent by Lee to Confederate President Jefferson Davis that Petersburg and Richmond needed to be evacuated.

Fisk was ready, handing over his payoff for the telegraph operator along with his scribbled message: “Go!” He had to get the one-word directive to Hargreaves in Halifax as soon as possible.

Fisk’s bribe could squeeze the message past protocol amid the flurry of military communiqués. But the operator could be forgiven for scoffing at his customer’s peculiar urgency. Lines running into Nova Scotia were highly unreliable, certainly not worthy of camping out at a telegraph office and paying a bribe. The message might not even arrive.

But Fisk had another ace up his sleeve. He had been privately assembling and staffing the last 50 miles of a telegraph line from Boston to Halifax. The project ran $100-$150 per mile, meaning Fisk had to earmark at least $5,000 of his secret investors’ stake to finish the connection. With only weeks’ notice, workers had to build around the clock, and only now — with the “Go” message en route — would Fisk know for sure if the line was ready.

The financial heart of London — known simply as “the City” — was one of its oldest sections. Within a web of streets sat the largest financial market in the world. While nearly 3 million people called London home in 1865, the financial hub was tied into a rather compact portion of the city, bounded by the Bank of England, Mansion House, and the monument to the 1666 Great Fire of London.

Fisk had groomed Hargreaves to circumvent the first roadblock: tracking down the bond traders. They wouldn’t be inside the 20-year-old concrete and cast-iron structure on Threadneedle Street, nor in its accompanying courtyard. The London Stock Exchange had made the decision at the outset of the Civil War not to formally quote either Union or Confederate bonds or permit their sale on the exchange. This meant that American bonds during the war, from both North and South, were bought and sold elsewhere.

In London, most of these transactions — fittingly, considering Fisk’s scheme — took place down an alley known as Shorter’s Court. The narrow lane off of Throgmorton Street sat on the backside of the Bank of England and in close proximity to the stock exchange. Some brokers even listed Shorter’s Court as their business address in the annual industry directory. When the exchange closed at 4 p.m., brokers would continue their work at Shorter’s Court. These tired brokers with half an eye toward an end-of-day pint would be perfect quarry for Hargreaves.

In addition to being blissfully unaware of the American news, the traders at Shorter’s Court had a political motive to continue trading Confederate bonds — many of England’s elite sympathized with or outright supported the Confederacy. The power of King Cotton influenced investment portfolios in London and many rooted for Confederate success, despite the moral abyss of slavery underpinning it all. In this way, the scheme hatched by the New England born-and-bred Fisk — even if Fisk’s money forever outweighed his ideology — was revenge against the British intelligentsia for picking the wrong side.

That “go” spread 650 miles through the private telegraph wires, including the 50 miles that had been tailored for Fisk like a silk suit. The message landed at Halifax as planned and confirmation of receipt reached Fisk. Hargreaves had his signal.

Their steamer took off from Halifax. In a matter of days they rounded Queenstown, Ireland. In less than a week, Hargreaves made it to Liverpool, from which a half-day’s journey over land brought him to London. So far, he was safely ahead of any word of Lee’s defeat.

How surreal for Hargreaves to stroll through the busy London streets and talk of the weather and the day’s news, while being the only person in the entire country — as far as he could tell — to know that a major war had ended. It was as if Fisk had managed to transport his operative several days into the future, like some character out of science fiction. But the rest of the world was hot on their heels.

In fact, a steamship called the Australian had already launched from New York. Onboard was a message dated April 5 that contained all the markets needed to know: After three days’ bloody battle Grant occupied Richmond and Petersburg, the detailed report began. If it remained on schedule, the Australian was approximately five days behind Hargreaves.

The clock ticked loudly for Hargreaves, with an uphill climb ahead. Small banks and brokers only had so much Confederate debt readily accessible. To pull off so many shorts in a matter of days, Hargreaves needed to move up the financial ladder in London overnight. The London market — while massive — was still dictated by a hierarchy of social circles. Hargreaves needed to scale the ranks like a character in a Charles Dickens novel, then extract himself before he was burned.

As the Australian sped across the Atlantic with the news that could ruin Fisk’s plans, its priceless intelligence was tagged only for one person’s eyes in England: Paul Julius Reuter. The German-born trailblazer ran London-based Reuters, a news agency underwritten by multiple newspapers and financial institutions. A man of slight build, Reuter started his agency on the continent utilizing pigeons to transport news, then relocated to London. He stood out for his ability to easily shift his conversations between English, French, and German, and for his dramatic whiskers. Unwittingly, Reuter was the greatest adversary to Fisk and his plan.

Reuter’s particular genius zeroed in on the importance of timely transmission of news for politicians and financiers alike. He even opened a second London office that dealt exclusively in American news during the war, a sign of what one critic saw as Reuter’s attempts at “monopolising the American News.” He located this office across the street from his Finsbury Square home to enable him to drop in when the latest dispatch arrived. The around-the-clock operation included cots in the office so that staff members could catch the occasional nap in between news bulletins. When news about the first battle of the war at Bull Run arrived in the summer of 1861, Reuter’s operator had fallen asleep on a cot. Only the appearance of Reuter in his pajamas and slippers looming over the young agent ensured that word got on.

Both Reuter and the British newspaper titan The Times had been enlisting steamer boats to meet ships off the coast of Southampton, England, to retrieve the latest from America. Competition pushed the boats toward Queenstown, Ireland, closer to the North American continent, but Reuter wanted to find an even quicker way to remain first. He used his own funds to construct a telegraph line from Cork to the Irish enclave of Crookhaven, on the jagged southwestern coast. The distance saved on the open water meant Reuter gained an eight-hour advantage on his competitors for transmitting news to London.

Now a few days away from the news steaming into Crookhaven en route to Reuter, Hargreaves had to complete the rest of his trades. But he also had to resist unloading his assets all at once. If he fed too large an investment through one house or broker, bankers with ties to financial titans like the Barings or Rothschilds could raise the alarm and ruin the whole plan.

Hargreaves especially needed to be on the lookout for the likes of Philip Cazenove, the senior partner in Cazenove & Son, the British stockbroking firm known by the 1860s for its ruthless efficiency in the stock and bond markets. One of the critical brokerages in the city of London, its methods and portfolio were held close to the vest and others spoke of the intimidating “aura” around the firm. Hargreaves had to thread a needle — he needed to both insert himself into the circles of these financial titans and avoid attracting special attention.

At 11:30 p.m. on Friday, April 14, the Australian, bursting with the biggest war news since Fort Sumter, finally cruised into the pitch black Crookhaven outpost in Ireland. Another steamer under Reuter’s control, the Marseilles, sped to intercept the incoming vessel. Phosphorous — which could be used in torches or propelled overhead—now illuminated the water. The Australian crew could now toss wooden canisters with the holy grail of news into the waters, to be scooped up by the crew of the Marseilles with nets on long poles.

The information was routed from Crookhaven to Cork, from which a telegraph was shot over the wires to London. That message reached the city in the early morning hours of Saturday. Reuter received it at his Finsbury Square office, just minutes away from where Hargreaves hustled to complete the scheme at Shorter’s Court. Now, it was just a matter of how quickly Reuter could get it into the papers.

Reuter was not only a purveyor of news, he had the ears of the most powerful people in the country. A few years earlier, he personally delivered news on the Trent Affair, an infamous international incident in the Civil War, to Downing Street. Reuter was granted immediate entry to the prime minister and beat the official dispatch from Washington by several hours. If Reuter decided to slip the news to a key member of the government or one of the banking titans before putting the news in the papers, Hargreaves could be cut off at the knees.

With Reuter now the second man in England to know the outcome of the Civil War on April 15, another world-changing event unfolded in America — President Lincoln died of an assassin’s wounds. Nobody in England would know for almost two weeks. (Reuter would ultimately get that assassination scoop first. In a sign of the ties binding news and commerce, London initially thought the tidings were rumors invented to manipulate the markets.)

With barely time to take a breath, much less sleep, Hargreaves had to finish reselling the bonds one by one to their respective brokers at Shorter’s Court. To be able to collect their jackpot, Hargreaves arranged for bills of exchange that could be cashed upon return to the States.

As one journalist noted later, the steamship Australian’s epic news “arrived too late to admit of the papers” on Saturday. But on Sunday, April 16, 1865, Reuter’s greatest triumph in the race for wartime news made front page headlines: Great Battles. Evacuation of Richmond by Lee. Occupation by Grant.

So ran London’s Observer, with similar headlines in The Guardian, The Times, and soon a flurry of others. Some papers ran awestruck descriptions of the Australian’s passage and Reuter’s receipt of a telegram, oblivious that a small band of American schemers had managed to beat the news by five days.

The news was out there for all to see and the city went wild as people tried to offload their Confederate debt.

But by this point Fisk’s scheme couldn’t be stopped. In mere days, Hargreaves had managed to buy and sell $5 million in Confederate debt, the equivalent today of tens of millions of dollars. The amount staggered the imagination by any era’s standard. When the shorts were closed, Fisk’s schemers had pocketed a profit of somewhere between $3 million and $4 million, the equivalent of tens of millions today.

Fisk had never had so much money in his life. He swept back into New York City, ready to climb back into the high life. His flair for the dramatic surging with his personal worth, the prince of peddlers had returned to the city stage with a new nickname “Jubilee Jim Fisk.”

Fisk promptly purchased an opera house that seated 2,600 — Pike’s at 23rd Street and 8th Avenue — and gave it a $250,000 makeover. Fisk changed the name to the Grand Opera House, installing a bronze bust of Shakespeare and marble floors, and revamping the grand staircase to befit the new name he bestowed on the establishment. Fisk even had a $1,000 marble and porcelain sink installed in his office above the theater, where he sat atop a throne constructed with gold nails. Fisk’s money was stored — what was left of it after his epic spree — in a safe that ran from the basement up the seven floors of the building.

Fisk’s personal residence at 313 West 23rd Street was equally fit for a king, and staffed by butlers, a cook, and coachmen. Fisk didn’t have one carriage — he had six. He also owned 15 horses, each with its own canary that could sing to the horses for their entertainment. Fisk could be seen around Manhattan with his four distinct attendants in tow. Two Black coachmen in the front outfitted in uniforms of all white, and two white coachmen in the back dressed all in black. Fisk seemed “divinely fashioned for the function of giving offense to people of taste,” as one biographer would write later.

But a hustler never stops hustling. While his coconspirator Hargreaves wisely receded into obscurity with his share of the take, Fisk began to blab about his Civil War scheme. No doubt his reputation soared among the swindling class, but he also became a magnet for high-risk ventures and borderline frauds looking for backing.

Fisk used a blossoming relationship with financier Daniel Drew to water down the stock price of the Erie Railroad Company by issuing spurious stock. The battle to corner the market on the company put Drew and Fisk into conflict with the railroad magnate Cornelius Vanderbilt. Vanderbilt poured $7 million into an effort to win over the Erie Railroad — an effort ultimately in vain. The practices of Fisk and Drew in the affair, dubious at best, necessitated their temporary exile to New Jersey to avoid prosecution in New York state.

Fisk later joined in a separate conspiracy with Jay Gould to corner the market in gold. The ensuing financial panic on Black Friday in 1869 almost ruined Fisk for a second time — to say nothing of the small recession it caused — and even led to a congressional investigation of President Ulysses Grant to determine if he was involved in the scheme.

Living fast extended to Fisk’s personal life. He hosted women in his offices above the theater with champagne and oysters from hot spot Delmonico’s. He allegedly hosted orgies that, as one writer put it, were “of the kind that brought Rome to ruin.” And, in 1867, he visited the famed New York City bordello of Annie Wood. While there, he found himself smitten by Helen “Josie” Mansfield, a divorced ex-actress turned showgirl.

Fisk’s wife split her time between Boston; Newport, Rhode Island; and Vermont, pursuing a relationship with a woman. Meanwhile, in New York, Fisk fell head over heels for Mansfield, a native of Boston. In short order, Fisk purchased her a four-story home on 24th Street, near his office, and provided her money for clothing and jewelry, some $30,000 over a single year. He had a private walkway constructed from his office to the 24th Street love nest to keep his illicit affair out of public view.

In the summer of 1869 Fisk went into business with Edward “Ned” Stokes — a man with similar self-confidence to Fisk, but a greater penchant for spending and better looks to boot. For Stokes and Mansfield, who met on New Year’s Day 1870, it was love at first sight. The affair quickly escalated and reached the point that Fisk confronted Mansfield. When he demanded she choose between him and Stokes in the love triangle, Mansfield quipped, “I don’t see why we can’t all three be friends.”

Fisk cut Mansfield off, but not until a flurry of letters passed back and forth between the two rife with accusations of infidelity in both directions. As for Fisk and his business partner, their shared interests in a Brooklyn oil refinery ended in court, though Stokes’s claims were ultimately thrown out. Stokes, who also received word that Fisk was throwing around accusations of blackmail against him, stewed in anger and vowed revenge.

At half-past 4 o’clock on January 6, 1872, Stokes waited at the Grand Central Hotel for Fisk. He paced on the second-floor landing outside the ladies entrance — it was Fisk’s preferred entrance, because he would not be noticed. As Fisk entered the hotel and ascended the stairs, Stokes came down to greet him.

“Now I’ve got you,” Stokes proclaimed.

Stokes fired two shots with a Colt revolver. One hit Fisk in the abdomen, the other in the left arm. Fisk lived long enough to identify his killer before he breathed his last. He was 37 years old.

Some 20,000 New Yorkers visited Fisk’s casket at the Grand Opera House. The man whose reputation was larger than life had elicited a fondness among the city’s working class — one biographer called him the “Tom Sawyer of Wall Street.” Wealthy New Yorkers, however, did not look too fondly on him. Another member of the New York Stock Exchange passed away on the same day, and the lowering of the flag outside of the exchange was delayed to ensure nobody could possibly mistake it as a gesture honoring Fisk.

After the viewings were over, Fisk’s body was returned to his home state of Vermont, where The Burlington Free Press marked his death with a quote from Mark Twain: “He made a nice, quiet corpse.” In England, of course, it was Reuter who broke the news to his readers.

James Fisk Jr. was buried at the Prospect Hill Cemetery in Brattleboro, his grave marked by a towering marble monument encircled by four scantily-clad women. It was the gaudiest tombstone in sight.

DAVID K. THOMSON is an assistant professor of history at Sacred Heart University in Connecticut.

Illustrations by Pat Kinsella for The Boston Globe.

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