When I was a kid in the 1980’s I came across a copy of The Book of Lists 1971. I loved it and read it cover to cover until it was dogeared. One of the stories was about a famous gourmand, “Diamond Jim” Brady, who once said of his favorite fish dish, “If you poured some of that sauce over a Turkish towel, I believe I could eat it all.” I shared that story with #13 and we researched Diamond Jim’s history together.

These days, people might recognize Diamond Jim’s name and nothing more, but in the early Twentieth Century he was famous, the subject of books, movies, and more. He was a symbol of the Gilded Age’s excess, known for his flamboyant dress and extravagant eating habits. He was also a real Horatio Alger rags-to-riches story, known for his legendary kindness and boundless generosity.

So let me tell you a bit about him.

Early Life of

James Buchanan Brady was born August 12, 1856, the second son of an Irish saloon keeper on New York’s Lower West Side. His father died in 1863, and his mother remarried a year later. His new stepfather took over the saloon and immediately put 8-year-old Jim and his 10-year-old brother Dan to work. The saloon slowly began to change from a neighborhood bar to a seedy hangout for rowdy sailors.

By 1867, the Brady boys had enough and started looking for employment elsewhere. Jim was only 11, but he was a husky boy, which allowed him to pass as someone several years older. Eventually he and Dan found employment as bellboys at the St. James Hotel off Madison Square. One of the first luxury hotels in that area, it was mostly a hangout for traveling salesmen. The dashing salesmen made an impression on young Jim, who dreamed of sharing their glamorous lifestyle. 

One of the St. James’ frequent patrons, John M. Toucey, liked the young man’s pluck and hustle and offered him a job. So Jim traded the life of a bellboy for the life of a baggage handler for the New York Central Railroad. In the evenings he sought to improve himself by taking classes on bookkeeping, penmanship, and telegraphy. 

Jim rapidly rose through the ranks of the New York Central. After a few months he was promoted to ticket agent. A year later he became a clerk, and soon after, chief clerk. In just under three years he’d gone from earning $1/week to earning $50/week.

He was only eighteen years old.

Then, disaster. When Jim had been promoted to clerk, he’d also convinced the New York Central to hire his brother Dan. But in 1877 Dan was fired — it was rumored he’d been embezzling. Because of the optics of the situation, the railroad felt it had to fire Jim, too. 

Toucey came to Jim’s rescue, finding his protegé a job as a salesman at the railway supply firm of Manning, Maxwell, and Moore. Jim had never been a salesman before, but he threw himself into his new role.

Jim’s sales technique was simple. 

• First, know your product. He knew the MM&M catalog backward and forward, from handsaws to hand trucks.
• Second, know your customer. Jim kept on top of industry trends, and wasn’t afraid to walk the tracks talking to workers and managers. That allowed him to anticipate a clients’ needs.
• Third, be friendly. In Jim’s case that usually meant treating a client a nice dinner, a few drinks, and a night at the theater.
• And when all else fails, be persistent. Jim once spent four days waiting for a meeting with George Baer of the Reading Railroad, who left him hanging each day. When Jim returned on the fifth day Baer was curious and asked Jim, “Why are you still here?” Jim grabbed his hat and said, “I’ve been waiting to tell you, sir, that you can go straight to hell.” It worked. Baer had a good laugh, and Jim had his meeting.

Soon Jim was Manning, Maxwell and Moore’s best salesman. With that came hefty commissions — and an unlimited expense account. That allowed Jim to be friendlier than ever, dazzling potential clients with the finest food, rarest spirits, and prettiest girls that money could buy.

Jim’s big break came in 1886. English inventor Samson Fox had created a new type of railway truck made from pressed steel, strong but light. It sold like gangbusters in England, but experts in the United States insisted it was too light to bear the weight of heavier American freight cars. Fox turned to Manning, Maxwell and Moore to see if they could help him. Unfortunately, they couldn’t. But they could refer him to Jim Brady.

Jim devised the perfect technique to sell Fox’s trucks: fear of missing out. He told the New York Central that if they didn’t give the trucks a fair shot he would take them across town to the Pennsylvania Railroad. So the New York Central agreed to a test run at their own expense. They liked what they saw, and ordered a hundred on the spot. Then Jim used the same technique on the Pennsy, who placed an order for 250. Soon every railroad in the country wanted pressed steel trucks. 

Fox was selling hundreds of trucks every week, and Jim Brady was earning a 33% commission on each and every one. Now he was a wealthy man.

Then a hot tip allowed him to snap up a floundering Pittsburgh steel company and convert it to the manufacture of pressed steel trucks. Now he was a ridiculously wealthy man. And he started living like one. 

To put it simply, Jim Brady was very very extra.

Diamonds, Wearing of

From his days studying the salesmen at the St. James, Jim knew that “if you’re going to make money, you’ve got to look like money.” So when he became a salesman, he took $200 and bought three stylish silk suits, some cravats, a durable suitcase, and a one-carat diamond ring. 

It seemed to work. Jim figured that if one diamond ring could impress potential clients, well, then, imagine how many he could land with more. He started scouring pawn shops for every jewel he could find. And wearing them.

(The jewels also became one of his sales tactics. If Jim couldn’t get past a stubborn secretary, he would empty a small purse of loose jewels onto their desk. When they inevitably squealed in delight their bosses would come out to see what all the fuss was about, and Jim would get his meeting.)

In 1884, Jim got his famous nickname at a meeting of salesmen in Cincinnati. When the roll was called, “Markie” Meyer, a cotton salesman for H.B. Claflin & Company, asked:

“Has anyone here seen Diamond Jim?”

“You mean Jim Brady, the big fat guy who doesn’t drink?”

“That’s him. Diamond Jim Brady, the pawnbroker’s curse.”

Now, there had been plenty of Diamond Jims before: flashy criminals, wealthy ranchers, baseball players, and Tammany Hall operative “Diamond Jim” Grady. But from this point on, there was only one Diamond Jim, because Diamond Jim Brady left every other pretender in his dust. Diamond dust.

He wore rings on his fingers sporting diamonds between one and seven carats. He had a diamond tie stick, a diamond scarfpin, diamond shirt studs, diamond cufflinks, and diamond buttons down the front of his waistcoat. He had diamond buckles on his belt, suspenders, and garters. He had a diamond-studded watch with a diamond-studded fob chain. And a diamond-studded matchbox, card case, pocketbook, walking stick, and umbrella. (Which also had a solid gold handle, to boot.)

And that was just one set! He had several dozen sets of themed accessories for every imaginable locale or occasion. 

At one point it was estimated that every time he left the house he had some $80,000 of jewels on his person. It was claimed that in the theater his diamonds provided more sparkle than even the brightest footlight. If anyone dared to claim that Jim’s diamonds were merely paste, he was always glad to prove them wrong by using his pinkie ring to engrave his name in the nearest pane of glass.

Of course, even Diamond Jim had his limits. He once told the papers:

“The trouble with American men is that they overdress. Now, I take it that I am considered a handsome man and one who would be called well-dressed. Never by any chance do I permit more than seventeen colors to creep into the pattern of my waistcoat. Moreover, I consider that twenty-eight rings are enough for any man to wear at the same time. Others may be carried in the pocket and exhibited as occasion requires. Diamonds larger than doorknobs should never be worn except in the evening.”

All joking aside, the flashy dress totally worked. It made Jim instantly memorable, and clients loved it. And it wasn’t just for clients. Jim also used his jewels to stand out from the pack of New York’s “dudes” — well-dressed young men who went to the theater and put on a show in the audience that rivaled the one on the stage.

They certainly caught the eye of many pretty young actresses. Most of them weren’t too interested in plain-looking, obese Diamond Jim Brady. But they were very interested in his unlimited expense account. And all the rich businessmen Jim could introduce them to.

To be fair. Jim wasn’t too interested in the actresses, either. Or maybe he was, but had no idea what to do if he caught one. But he was also very interested in how they could help him earn commissions.

So, win-win on both sides.

Eating Habits of

Diamond Jim had always loved to eat. As soon as he had his own independent income he would spend his days off wandering the docks of lower Manhattan, chowing down on fresh oysters and eel pies. He had a big appetite, and it helped make him a big boy.

Well, as he grew, he became a big man. No longer content with dining down at the wharf, he now frequented New York’s most famous steakhouses and oyster bars. And if anything, his appetite increased. Somehow infinitely.

If you think I’m joking, well, here’s what a typical day’s food might look like for Diamond Jim Brady.

• For breakfast, a towering pile of hot cakes with melted butter and maple syrup, half a dozen poached eggs, hash browns, grits, corn bread, muffins, several chops, a small beefsteak, and a few glasses of milk.
• As a mid-morning snack, half a dozen oysters on the half-shell.
• For lunch, more oysters, deviled crabs, two broiled lobsters, roast beef, a salad, and half a pie, washed down with orange juice.
• At tea-time, more oysters and some lemon soda.
• For dinner, even more oysters and crabs, a tureen of green turtle soup, some broiled shad, a crown roast of sheep, a thick sirloin, a couple of canvasback ducks, sherbert, and various vegetables on the side.
• And for dessert, an entire pastry tray and a five pound box of chocolate bon-bons enjoyed over coffee.

About the only thing Jim didn’t partake of was alcohol. Working in his stepfather’s saloon had cured him of any desire to drink. Instead, he drank orange juice, lemon soda, and ginger ale by the gallon.

Oh, and if you were dining with him and couldn’t finish your meal? He would gladly eat all the scraps left on  your plate, and then call for more bread. Jim once joked that his method of pacing himself was to start every meal four inches away from the table, and stop when he felt his belly touch the edge.

Needless to say, he was enormously obese. For most of Diamond Jim’s adult life, he  topped the scale at more than 300 pounds. 

Later in life, Jim started to suffer from diabetes and other complications from his obesity. So his physician put him on a diet and told him to eat a light dinner. Of course, for Diamond Jim, being on a light dinner still meant two dozen oysters, a filet mignon, some asparagus, and a whole watermelon.

Lillian Russell, relationship with

In 1893, Jim’s quest for fine food and fancy things led him to the Chicago World’s Fair and Columbian Exposition. While there, he ran into an old friend — “The American Beauty,” Lillian Russell, the most famous and beautiful actress in the country, who was performing at the Columbian Theater on the Midway.

Lillian knew Jim from his days as a “stage door Johnny” in New York. He invited her to dinner at George Rector’s Café Marine. She accepted, and the two of them bonded over — I kid you not — their mutual love of corn-on-the-cob. And just about everything else on the menu. 

And they had lots more in common, too. They were both shunned by high society because of their lower-class origins and vulgar habits. In Jim’s case, that meant his gaudy wardrobe, crass language, and gluttony. In Lillian’s case it was more about her tempestuous love life, a non-stop parade of adultery, bigamy, and even one sham wedding to a gay man.

Well, Jim was smitten. And Lillian… was not, but definitely liked Jim and appreciated his attention. Soon they were constant companions, not quite an item, but something more than mere friends. BESTIES! 

It’s easy to see what Lillian got out of the arrangement. Jim showered her with expensive presents, treated her to the finest meals, and was supportive of her career. His very presence kept unwanted suitors away, and he politely moved out of the way when she actually fancied one of those suitors.

And Jim? Well, he got to be the envy of every man in America, because he had the most beautiful woman in the world hanging off his arm. It was great publicity, and that was enough for him. Most of the time.

Once, Jim offered to buy Lillian an extravagant gift if she could match his consumption at dinner, course for course. Lillian agreed, and then made a quick trip to the ladies’ room to discreetly remove her corset. Needless to say, she won that bet.

And hey, it all worked out in the end. In 1897 Lillian got engaged to one of Jim’s friends, handsome young copper tycoon Jesse Lewisohn. At the same time, Jim got engaged to a gold-digging shopgirl named Edna McCauley. She was no Lillian Russell, but hey, she put out.

Conspicuous Consumption

Lillian wasn’t the only thing Jim acquired at the Chicago World’s Fair. He bought an “electric brougham” from Frank and Charles Duryea, which he had shipped back to New York on a special flatcar. It was the first automobile on New York streets. He had his chauffeur drive it around Madison Square at the breakneck speed of 11 miles per hour, drawing crowds and snarling traffic. After that, he was ordered by the police to only take it out at night.

As his health started to decline, Jim’s doctor ordered him to lose some weight. So he and Lillian took up horse riding. That took, you know, effort, so he stopped. But Jim became obsessed with horse racing and sunk thousands of dollars into racing stables. After one successful racing season he threw an enormous blowout at the Hoffman House restaurant for fifty associates in the racing world. The party started at 4 PM on a Sunday and raged on until 9 AM Monday morning, and cost him an estimated $100,000. That doesn’t include the party favors, a diamond-studded watch for every man and a diamond brooch for every woman, which cost him another $60,000.

Of course, if you’re going to race horses, you might as well have some place to raise them. So Jim bought a farm in Long Branch, NJ and turned it into an extravagant stage where he could play at being a farmer, complete with champion cattle and gold-plated milk buckets. Any produce he actually managed to raise was given to the “needy” — mostly theater folks — who also used the farm as a weekend retreat for their canoodling. 

And the farm was nothing compared to Jim’s townhouse on Central Park West. He spent almost half a million dollars to have it decorated — and that’s in 1897 money! Every room was decked out with Louis XIV furniture and fine Oriental carpets. There was a full professional kitchen, the greatest kitchen in New York, or at least the greatest kitchen that wasn’t in a restaurant. The game room had Tiffany lamps, a billiard table made from mahogany and studded with semiprecious stones, and poker tables with chips made from pearl and onyx. There was the “tiger room” for guests, which was decorated with actual tiger skins. There was a “Turkish room” for rumpy-pumpy that was decorated with statues by Rodin. The bathroom tub was so big a grown man could lie down in it and take a nap, which Charlie Chaplin reportedly did. He even had wardrobes filled with loose jewels and jewelry to give houseguests. It sounds almost too fantastic to be real. Like Graceland. Or wherever Richie Rich lives.

When bicycles were all the rage, Jim had to have one. A top-of-the-line bike cost about $20 at the time, but Jim’s? It cost $2,000. It was a custom order, with an extra-large seat for his extra-large seat, gold plating on the frame, and silver plating on the spokes. With a few diamonds and rubies sprinkled on the handlebars, just to add a touch of class. He bought a dozen of them for his personal use, and a matching one for Lillian Russell. Once again, they were rarely used.

Instead, Jim invested in a rare “bicycle built for three” that he used to take his female friends on excursions to the Jersey shore. Of course, Jim and his paramours didn’t actually do any of the pedaling. That task fell to Jim’s personal trainer, Dick Barton, who had to put out enough power to compensate for 500 pounds of dead weight. Probably more, since most of these excursions involved stopping at every beer garden between Guttenberg and Bayonne to load up on sauerkraut and schnitzel.

Jim also spent lavishly on others. In 1896 he started sending Christmas boxes to everyone in his address book, from CEOs to the lowliest railroad worker. They were packed with full Christmas dinners — 20 lb. turkeys with all the fixings, cranberries, jellies, dried fruit and nuts. Eventually, the tradition of Christmas boxes evolved into the “Brady Benevolent Society,” a select group of 300 friends who received weekly presents that rotated between boxes of chocolates, baskets of fruit, candy, and flowers. 

On a trip to Boston, he sampled some chocolates from local confectioner Page & Shaw. He liked them so much he bought 20 pounds of chocolates, and then ate half of them on the train ride back to New York. Jim told the company he planned on regularly buying boxes for himself, and for everyone in the Brady Benevolent Society, too. When the company protested that they didn’t have the capacity to turn out 300 pounds of chocolate a month, just for Jim’s exclusive use, he cut them a check for $150,000 to expand their production facilities.

That generosity didn’t end with Jim’s friends. He was known to give $100 to any woman who approached him with a hard-luck story, even when it was obviously fake. He liked to think he was just being helpful.

Of course, Jim also made use of some of these fallen women to throw some of the wildest debaucheries New York has ever seen. A typical Diamond Jim Brady joint might feature naked ladies on swings, naked serving girls who sat with trays of food balanced on their thighs, or even dancing girls baked into a pie.

It should be noted that not everyone was happy to be on the receiving end of Diamond Jim’s largesse. Some people were embarrassed and stressed by their inability to reciprocate. But if you refused his gifts, there was a possibility he might turn violent. He once raged, “God damn it, if it gives me pleasure to send you presents I’m gonna go right on sending ’em whether you like it or not!” When someone refused to take one of Jim’s gold bikes, Jim threatened to wrap it around his neck.

Filet of Sole Marguery

In 1899, famed Chicago restaurateur Charles Rector opened a new restaurant on Longacre Square (now Times Square). Thanks to the fine food, unparalleled service, and proximity to Broadway theaters, it quickly became the place to eat in New York. Patrons ran the gamut from O. Henry to William Randolph Hearst.

Their best customer, though, was Diamond Jim Brady. He had a sentimental attachment to Rector’s — his first date with Lillian Russell had been at Rector’s Café Marine, the only restaurant inside the 1893 Chicago World’s Fair.

On a trip to Paris, Diamond Jim had fallen in love with the filet of sole at the Café Marguery. Jim asked Rector to recreate the recipe. Or rather, he demanded that Rector recreate the recipe, or he would take his extensive business elsewhere. Charles Rector immediately forced his son George to drop out of Cornell Law and travel to France and learn the secret recipe.

Depending on who you ask, this either went one of two ways. 

• The first version of the story is that George Rector traveled to Paris and talked his way into a job as a dishwasher at the Café Marguery. He spied on the kitchen for three weeks until he learned how to make the sauce, and then fled back to the United States in the middle of the night.
• The second version of the story is that George spent a year working at the Café as an apprentice, earning his cordon bleu and learning the recipe directly from the master.

Regardless of what really happened, George Rector returned to New York with the recipe in hand. When his boat pulled into the harbor, he was greeted by Diamond Jim Brady, standing on the wharf, and bellowing, “Did you get the sauce?”

Well, George Rector made Diamond Jim a double helping, and Jim licked the plate clean. He patted his stomach and declared, “If you poured some of that sauce over a Turkish towel, I believe I could eat it all.”

Later Years

Alas, all good things have to come to an end eventually.

In 1895, Jim and his mother had a falling out. She had assumed that she would be moving into his palatial Central Park West house once it was completed, but it soon became apparent that wasn’t the case. So she started picketing his office and badmouthing him to everyone passing by. Jim responded by trying to get her committed to a sanitarium. That was blocked by his brother Dan, who claimed Jim was just trying to gain control of her money — which was ridiculous, since all of her money came from Jim in the first place. Jim washed his hands of the whole affair and never spoke to his mother or brother again.

His mess of a family was nothing compared to his mess of a love life. In 1906, Lillian Russell’s fiancé Jesse Lewisohn fell ill and was prescribed a course of bed rest. Lillian was on tour, and couldn’t take care of him, so Diamond Jim graciously allowed Jesse to rest at his farm, where Jim’s fiancée Edna could take care of him.

I think you can see where this one is going. Jesse and Edna fell in love. They broke the news to Jim, who did not take it well. He flew into a rage, cursing the lovebirds furiously and calling them every name he could think of. And then he went away for a good cry. And to break the bad news to Lillian.

It was one of the few times in his life when his public facade cracked. He confessed to his good friend Jules Weiss, “What’s done is done. I asked her [Edna] plenty of times to marry me and she always refused. Do you know why? It’s because there ain’t a woman in the world who’d marry a fat, ugly guy like me.” 

Jim tried to rebound by proposing marriage to Lillian in 1910. He did it in the least romantic way possible — by presenting her with a check for $1 million. Lillian politely refused, telling Jim that she was done with love and didn’t want to ruin a beautiful friendship. Of course, Lillian wasn’t actually done with love, and two years later married Pittsburgh newspaper publisher Alexander Pollock Moore. Publicly, Jim wished them well, but privately, his heart was broken.

In 1912, Jim started to have severe indigestion. He went to his physician, expecting nothing more than a stern lecture about eating less and losing weight. Instead, he got a referral to a gastrointestinal specialist at Johns Hopkins Hospital, where he was diagnosed with kidney stones. And also Bright’s disease, diabetes, several UTIs, hypertension, and an inflamed prostate. It did not look good. Fearing he was near death, Jim burned most of his private correspondence, including $250,000 dollars in IOUs that were owed to him.

Under most circumstances, Jim’s diabetes precluded a surgical operation to remove the kidney stone. Fortunately for Jim, Johns Hopkins had a brilliant urologist, Dr. Hugh Young, who had developed new techniques that made it possible. But first the hospital had to prepare reinforced beds and operating tables to accommodate Jim’s enormous bulk.

All anyone in New York knew was that Jim was in the hospital. Rumors began to fly that he was planning to have a second stomach installed. 

The operation itself took only a few minutes. Jim’s recovery took weeks, but Dr. Young wouldn’t be there to see it — he had a medical conference in London to attend. When Brady found out, he made sure Young was well taken care of. He arranged for the surgeon to have free rooms at the Vanderbilt hotel, front-row tickets to Broadway’s hottest show, and a first class berth for the trip to Europe.

And Jim’s generosity didn’t end there. He donated $200,000 to Johns Hopkins to create an institute of urology. The James Buchanan Brady Urological Institute is still in operation today. 

After the operation, Jim had to settle for a more modest diet. Of course, that diet was still extravagant by everyone else’s standards. Breakfast consisted of fresh cantaloupe, oatmeal, bacon, eggs, and toast with marmalade. Lunch would be some clams, broiled fish, vegetables, potatoes, and a light souffle. And dinner consisted of salad, turtle soup, more broiled fish, a guinea hen, vegetables, ice cream, cake, and cheese.

Even with his kidney stone removed, Jim’s health was still deteriorating. His diabetes continued to get worse and now he was suffering from angina pectoris. At the end of 1916, he had an attack of gastric ulcers and figured the end was near.  He moved into a suite at the Shelburne Hotel on the Atlantic City boardwalk, and had a glass-enclosed veranda built so that he could watch the sea without going outside.

He died in his sleep on April 13, 1917.

Jim’s last will and testament completely shut out his brother Dan, but set aside $25,000 for his half-sister and her son. He also made some small gifts to friends and employees.

But the bulk of his estate went to charitable contributions. He made $10,000 bequests to the New York Central Employee’s Hospital, the Newsboys’ Lodging House, the Roman Catholic Orphan Asylum, the Children’s Aid Society, and the Actor’s Fund of America. The remainder of his $12 million estate was to be divided between Johns Hopkins Hospital and the New York Hospital.  

Final Thoughts

You know, when you look at pictures of Diamond Jim, he’s not a terrible looking man. If he was around in today’s society, he would easily have gone to a plastic surgeon. He might not have done anything about his weight. Maybe he’d have gastric bypass. Definitely probably would’ve, actually. He had a full head of hair… He didn’t slouch… He was not a bad looking man.

It just sounded like he was very insecure about who he was. It also sounded like he really didn’t have any way to relate to women. Growing up in a bar there probably weren’t very many positive female relationships that he thought. It’s very sad. 

A sad situation for man. An empty life and he chose to fill it with excesses — food, diamonds, jewels, living a flashy life. A very sad life. It seemed like however much he filled himself, he could never get full enough.