Racetrack plunger Riley Grannan, 1869-1908
Kevin on Jun 29th 2009
“It’s all a joke; it doesn’t amount to anything.”
These were the last words of Riley Grannan as he lay dying of pneumonia in Rawhide, Nevada. Grannan was a gambler and bookmaker, who won and lost his fortune multiple times playing the races.
Image: Sketch of Riley Grannan from an 1895 newspaper article
The name Pittsburg Phil lives on in the lore of racing but, during his day, Grannan’s fame matched and, at times, superseded that of the man known today for his Maxims.
Grannan – the son of a poor tailor – was born in Paris, Kentucky in 1868. While his early history is muddled, according to an article in the San Francisco Call in 1899, he left home when he was 12 years old. While working as a bell boy at a New Orleans hotel, he secured his first position as a spotter and runner for a prominent bookmaker. The 1899 article reported:
“[Grannan's] first regular start toward his present position was when Botay, who is well known, especially in the West, as a man who ‘ran a shoestring up into a bankroll’, gave him a position, and when he was 20 years old [1888], branched out as a full-fledged bookmaker, bent on a mission of enlightening the racing world.”
He didn’t exactly enlighten the racing world but he quickly became a well know character at tracks across the country. His betting activities, during the peak of his fame, were as much a part of race reporting as the races themselves. By 1894, his name appeared frequently next to those of the gambling ring’s biggest “plungers” — the term used to describe gamblers who wagered wild sums on racing during this era.
Image: Headline from San Francisco Call, December 1894
An article in the Salt Lake City Press in 1895, compared Grannan with Pittsburg Phil:
“Physically these two race track sights are much alike and the similarity extends to their mental structures. Both men are usually reticent. They seldom speak and then only a word or two. Each keeps to himself and never indulge in that cheapest of race track privileges – giving tips to his friends…”“…Smith keeps available cash on hand to the tune of $250,000. That is the sum he invests in the betting business. Everything he makes above that figure he invests in conservative, interest bearing stock and bonds. If a long streak of reverses should wipe out that $250,000, he says he will quit the betting ring and retire to his outside fortune.
“Grannan has no similar anchor to windward. When he goes broke he is broke in dead earnest. Outside of the money he has on hand, the only investment he ever made with the hundreds of thousands he owned, is a $10,000 house in Paris Ky., which he gave to his mother…
“…Smith is the better business man of the two, but Grannan is the biggest plunger. That is the only difference between these two young men.”
Image: Sketch of Pittsburgh Phil and Riley Grannan,”The most famous plungers the world over,” 1895
While most reporting on Grannan during this period documents him placing bets, he continued to book bets as opportunities presented themselves. Taking money on – what he believed to be – vulnerable favorites was a trademark of his bookmaking activities.
It was this method that made him part of the lore connected to the match race between Domino and Henry of Navarre in 1895. His actions in the gambling ring before the great race were described in a number of newspapers over the years. Here is one of those reports from 1896:
“When Henry of Navarre and Domino ran a match race at Gravesend, Grannan, who was very intimate with Byron McClelland, then owner of the former horse, did some of the most phenomenal plunging ever seen in the east.“Mounting his box he took off his coat and announced that he was going to bet his last dollar on Henry of Navarre. Then he chalked up a point better odds on Domino than was offered by anybody else in the ring and invited the public to come on.
“Mike Dwyer sent in $10,000 which Grannan took, Ike Thompson handed over $10,000 more, then came another $10,000 from Mr. Dwyer, after which two $5000 bets were handed up by a commissioner said to represent James R Keene, owner of Domino. Thousands of dollars more in small bets came in but Grannan never winced, never once cut the price.
“In all he took in $62,000 and that represented all that the people had to bet, for it was still fifteen minutes before the race when the young plunger took in his last bet. It was the first time that easterners had been bet to a standstill and Grannan did something then that he has never done since. He hurled sarcastic remarks at the crowd and invited them to come and break him. It is the only time that anyone can remember when Grannan lost his temper.
“The race resulted in a dead heat, and though Grannan had to pay half the face value of every ticket he issued, he won some $15,000 on the race after all.”
His daring during the match race brought with it scrutiny from the racing press. An article in the New York Daily Tribune implied something untoward about the way Grannan took action against Domino [read more about press reaction to the result].
In 1898, he returned to the United States but appears to have avoided the New York tracks, visiting mainly the mid-west and California.
A 1901 article declared that the days of big bets had passed and referred to Grannan as one of the last of the great plungers.
Two years later, in 1903, a St. Paul newspaper reported this:
“With the old spirit, to dare all in one plunge. Riley Grannan, in many respects the most spectacular plunger the American turf has known, placed his all—$18,000—on O’Hagen, at the Crescent City track, New Orleans. His judgment, for once, proved at fault. Andes galloped home ahead of O’Hagen. Today Grannan is a wreck, financially and physically. He is confined to his room with an illness so severe that his recovery is doubted. Whether he regains his health is not, the turf will never see his face again, he says.”
In spite of this promise, Grannan did return to the track, starting a bookmaking operation in New Orleans. He also formed the Riley Grannan Co., Ltd., a tout business that advertised in southern newspapers.
It is not clear, what finally drove Grannan from the track once and for all, but it is fairly certain that sometime in 1903 or 1904, he did indeed walk away.
He borrowed money from track acquaintances and opened a saloon in the gold mining town of Rawhide, NV. Like all towns that sprang up in Nevada during the gold and silver boom, it was a rough place.
While not yet 40-years-old, he had already lived many lifetimes, full of wild highs and desperate lows. It finally caught up with him in 1908:
“…after a night at the gaming tables Grannan, a heavy loser and broke again, went forth to a round of dissipation at the resorts of the town and contracted pneumonia which brought an end to his life in the world…”
Before his body was shipped back to his childhood home in Kentucky for final burial, his remains sat on an express wagon at the rear of the saloon he purchased just a few years prior. Surrounded by a “rough, unkempt crew” — his friends bid him a final farewell.
W.W. Knickerbocker, a defrocked minister, delivered a eulogy where he called his friend “…one of the greatest plungers that the continent had ever produced.” He said Grannan was “…as placid and gentle as I have ever seen…absolutely invincible in spirit [and] a ‘dead game sport.”
While Grannan’s death bed proclamation implied a life wasted, most horseplayers can appreciate Grannan’s tale as a life well lived.
SOURCES, NOTES, AND OBSERVATIONS
This post took me much longer then expected. The amount of material that can be found about Riley Grannan is astounding. It is surprising that so much detail can be found about a gambler in a relatively small sample of newspapers. Below are the main sources I used but there is much more at the Library of Congress’s Historic American Newspapers: http://chroniclingamerica.loc.gov/
“Betting Rings Doomed,” New York Herald Tribune, September 23, 1894
“Grannan in Luck,” San Francisco Morning Call, December 29, 1894
“Career of the Premier Plunger,” Salt Lake Herald Sunday, September 29, 1895
“Smith and Grannan,” Salt Lake Herald, July 19, 1896
“Rilery Grannan Again Wins Fame and Fortune,” San Francisco Call, July 16, 1899
“Days of Big Best Past, St. Paul Globe, April 15, 1901
“Plunger Riley is Broke,” St. Paul Globe, January 20, 1903
“Riley Grannan Dead,” New York Times, April 4, 1908
“A Word of Eulogium of Riley Grannan,” Bourbon News (Paris, KY), April 17, 1908
The photograph of the Gravesend betting ring is from
Michael Immerso, Coney Island: The People’s Playground (Rutgers University Press: 2002)In a final twist in the story of Riley Grannan, the eulogy delivered in Rawhide by his friend W.W. Knickerbocker was published soon after he died. It was digitized as part of UNLV’s digital history project about southern Nevada. Read it here: http://digital.library.unlv.edu/boomtown/dm.php/snv/4593
Nevadaweb.com also has a page about the famous eulogy here: http://www.nevadaweb.com/ghp/riley1.html
Plan to do more about Riley Grannan in the future – this is a pretty long post but it could have been much longer.
The lives of gamblers like Pittsburg Phil, Pack McKenna, and Riley Grannan are fascinating. One of these days, I am going to create a Horseplayer Hall of Fame website. Considering that horseplayers have been the glue that has held the sport together, it seems appropriate that they should have their own Hall of Fame (even if it is virtual). Let me know if you have someone you would like to nominate.
Hope everyone enjoyed Rachel Alexandra and Zenyatta this weekend. It will be great if we ever get to see them head to head. Would love to see one (or both) in the Delaware Handicap (unlikely, I know).
THANKS FOR READING AND GOOD LUCK!
Filed in 1936, Pittsburg Phil, Riley Grannan, famous gamblers, gambling, historic horseplayers, thoroughbred racing history | 3 responses so far
"Pack" McKenna – One of Racing’s Original Handicappers
Kevin on Feb 25th 2009
I received an email a few months back from Jim McKenna of Carlsbad, California. He wrote to me about his great-grandfather, Patrick “Pack” McKenna (pictured, circa 1890), a well known New York-based handicapper who started playing the races in the 1880s and became somewhat of a celebrity in racing circles for the remainder of his life. After a number of email exchanges, a phone conversation, and a series of interesting sources kindly sent to me by Jim, I put together this article about his ancestor who, like Pittsburg Phil, is one of the founding fathers of modern horse players.
“Pack” McKenna was described in newspaper accounts as one of the “original handicappers”, “the oldest and most successful of the betting handicappers”, and “the best known handicapper on the American Turf.” According to census records, “Pack” identified himself as a “real estate broker.”
Family lore tells us that McKenna and his brothers did indeed have a real estate business but “Pack” spent most of his adult life at the racetrack. His name appears in newspapers for the first time in relation to his chosen vocation starting in the mid 1890s. By that time, it seems that McKenna had already accumulated a significant bankroll playing the races. As early as 1894, “Cad” Irish, a long time friend of McKenna, was being identified as the “old original handicapper” — a moniker that would eventually be attached to “Pack” as well.
Man standing in back row identified as “Uncle Pac”
(Click image to enlarge)
In the 1970s, McKenna’s son wrote a history of his father and offered some insight into how he became such a successful horse player:
“…before 1900 no past performance charts were ever published and solid info was hard to come by. Pack overcame this by having men posted at the start and the finish as well as the quarter poles. From this information the running of the race was reconstructed and he was able to prepare his own charts which were most helpful and permitted him to be successful. The charts were substantially the same as those published in the papers today.”
It is difficult to identify the “inventor” of racing charts but one thing is certain: “Pack” McKenna and his partners in New York were compiling the objective data that we take for granted today and using it to gain a significant advantage at the track in the 1890s and possibly earlier.
The family account has supporting evidence in an article published by the Brooklyn Daily Eagle in 1899. In the article, the author wrote, “The handicappers of the Botay, McKenna, and Irish type made their money 10 years ago when handicapping or ‘doping’, as it was more generally called, was confined to a select few. Then they frequently secured long prices against horses which should have been odds on favorites. Now, almost every patron of a race track carries his dope book, and when a horse wins at a long price it is because his true form has been hidden or the jockey is not a fashionable one.”
In another article written in 1900 also from the Brooklyn Eagle: “Of the betting handicappers, Irish, Botay, and McKenna have been very successful. It is not an unusual occurrence for one of these men to spend several hours doping out a single race.”
["Doping" was a term used to describe handicapping in the 1890s. "Dope" was slang for information into the 20th century.]
Much of the advantages Pack McKenna and his associates gained in the 1890s were lost when other gamblers began to understand the value of objective information in their wagering. The Daily Racing Form began publishing chart books in 1896. By 1900, the New York Evening World and other newspapers had started to publish race charts that included running lines similar to the ones likely being produced by gamblers like McKenna. In 1905, the Daily Racing Form provided past performances for the first time. Much of the “doping” done by a small band of handicappers starting in the 1880s was now being offered to anyone who made a small investment in a Racing Form or daily newspaper.
Even though his advantage as a handicapper lasted no more then 15 years, Pack McKenna spent most of his adult life at the races. His experience gained him a level of notoriety and skill that made him a familiar and successful character on the east coast racing circuit and beyond. For nearly sixty years, until his death in 1939, “Pack” McKenna was a horseplayer.
Image: The well traveled “Pack” in Havana, Cuba. Late 1920s
He lived much of his life in Bay Ridge, New York, in close proximity to the New York tracks, but spent a great deal of time on the road following the races. In 1908, like all those associated with racing in New York, he was effected by the enforcement of the Hart-Agnew Law that banned bookmakers from tracks. In fact, “Pack” McKenna was involved in one of the first arrests under the new law at the Gravesend Racetrack in Coney Island.
The account of the arrest was captured by a New York Times reporter under the headline “Bettors in Check”. The incident occurred between McKenna, who the Times called “one of the oldest and most successful of the betting handicappers, and George Cafferata, identified as a “professional betting man” and former “bookmaker.”
According to the article: “…When McKenna approached [Cafferata] on the lawn and asked what he would lay against Simon Pure in the Steeplechase, Cafferata made answer, ‘Two to one.’ ‘I’ll bet you fifty,’ said McKenna, and Cafferata answered, ‘You’re on.’ Then a policeman placed the surprised Cafferata under arrest for betting in violation of the law.
“‘Hold on,’ exclaimed McKenna to the policeman, ‘if it is wrong, the bet don’t go. It’s off, Cafferata.’ And Cafferata agreed that it was no bet.
“The point was too fine for a sleepy policeman doing extra duty on his day off, and he took Cafferata along. He hesitated a moment when someone suggested that McKenna be arrested, too, for relieving Cafferata from the bet, on the ground that it was the same in purpose as compounding a felony, but the policeman said that was not included in his orders…”
The ban did little to deter “Pack.” It seems he spent a great deal of time in Maryland during the New York ban. He continued to travel with his old pal “Cat” Irish and developed an influential group of acquaintances in the Washington D.C. area that included Clark Griffith, owner of the Washington Senators, and Ed Walsh, a member of the Senators board of directors.
Image: Photograph of “Pack” McKenna with Ed Walsh (from unidentified Maryland newspaper, circa 1930.
In 1916, a dinner was held for McKenna at the Willard Hotel in Washington D.C. to celebrate a perfect 7 for 7 day he had picking winners at Bowie. It was attended by Griffith and Walsh as well as other influential Washingtonians. By that time, his circle of friends included influential men within the business and political worlds, among them Tom Brahany, personal secretary to two U.S. presidents.
In 1919, he wrote an article for the Washington Post about handicapping. The biography accompanying the article included this description: “P.J. (“Pack”) McKenna probably is the best known and the most successful handicapper on the American Turf…He has in his private library a more extensive collection on turf data then perhaps than any other man who goes to the races.”
In 1921, he became such a figure among the New York horse set that an article about the meet at Aqueduct reported his absence from the track: “The many friends of “Pack” McKenna will be glad to learn that he is convalescing nicely in the Brooklyn Hospital from a serious operation…He was one of the original handicappers. His genial personality, his keen insight into racing conditions and his true Americanism gained for him many staunch friends. They have missed him during his illness and will be glad to greet him on his return to the turf.”
Another New York paper, in 1921, falsely reported his death. The article said that McKenna “…called the office of the National Form Sheet to indignantly deny that he was dead. ‘Now I may not be a Man o’ War,’ chuckled good-natured Pat. ‘but I feel as frisky as a two year old. The Lord being willing, I’ll be out at Laurel this afternoon trying to separate the wheat from the chaff.’”
Family history tells us that McKenna lost a significant amount of money in the crash of 1929. Evidence that his investments and income, by that time, were in the “legitimate” arena of stocks, bonds, and real estate (love the irony there!). In spite of this loss, he continued attending the races throughout the 1930s.
To the end, “Pack” maintained his race records in two large steamer trunks that teemed with notes that only a true horse player could appreciate. Even when he could no longer go to the track, his grandson, who was 10 when his grandfather died, remembers him hovering over his notes and charts at the dining room table. He studied and maintained his “dope” until the end.
He died at his daughters home in Douglaston, New York in 1939.
A letter written by a friend from the Hotel Pershing in Miami, after receiving news of McKenna’s death, says a great deal about a life well lived. In the letter to Pack’s daughter, S. Winter wrote: “Every one I meet at the races, and he had more friends than any one I know, speaks of him with loving kindness and regrets his loss. He had such a wonderful disposition and sense of humor….Let it be a consolation to you and all the family to realize the love and respect that all had for him.”
So much for the image of the degenerate horse player — “Pack” McKenna was a class act all the way.
SOURCES, NOTES, AND OBSERVATIONS
I want to thank Jim McKenna for sharing the outstanding research he has done on his great-grandfather. All the images used here are from Jim’s private collection. “Pack” McKenna is an important but forgotten figure in the history of racing — I am thrilled to be able to share his story here. I will post the article “Pack” wrote for the Washington Post and more on the origination of race charts, past performances, and other subjects that I uncovered while researching this piece in future posts. I find the history of playing the races during the era of “Pack” McKenna, Cad Irish, and Pittsburg Phil to be tremendously fascinating.
Obituaries for “Pack” McKenna appeared in:
Binghampton Press, February 6, 1939
The Blood Horse, February 11, 1939
Brooklyn Daily Eagle, February 1938 (the longest of the obits)
The Morning Telegraph, February 7, 1939
___________________________________
Looking forward to the Fountain of Youth this weekend. I think we have an interesting group of horses on the Derby Trail. At this time last year, I was still hunting for an intriguing horse to follow (and never really found one). This year I have a rooting interest in Larry Jones’ two colts (Old Fashioned and Firesian Fire). Old Fashioned is my hometown horse for 2009 (owned by Delaware’s Rick Porter and ridden by Del Park King Ramon Dominguez). The “hometown angle” (Philly-Delaware) has played well on the Derby Trail the past few years (Smarty Jones, Afleet Alex, Barbaro, Hard Spun, Eight Belles, and Dominguez rode 2nd place Bluegrass Cat in 2006).
THANKS FOR READING AND GOOD LUCK!
Filed in 1890s, Hart-Agnew Law, New York gambling ban, Pack McKenna, Patrick J. McKenna, famous gamblers, historic horseplayers, origins of handicapping, race charts | 5 responses so far
What Killed Pittsburg Phil? 1905
Kevin on Jan 27th 2009
I recently stumbled across an interesting site (www.fultonhistory.com) that has thousands of pages from New York state newspapers as well as other historical documents and images. It is difficult to navigate but worth the effort once you figure it out. In doing my usual searches, I came across a fascinating article on a familiar topic.
Image: George E. Smith (aka Pittsburg Phil) circa 1890s. Image from Tod Sloan by Himself published in 1915. Sloan was a jockey and a friend of Pittsburg Phil. He devoted an entire chapter to him in his memoir.
Pittsburg Phil, the founding father of horse players, died in February 1905. A month before he died the Utica Sunday Journal picked up a story from the New York Sun. It seems word began to spread about the failing health of the famous gambler whose exploits in the betting ring were well documented in the New York press. The story presents a theory behind his demise:
“…Those who know Pittsburg Phil best said that his nervous system has been shattered because of the intense strain and worry caused by his extensive operations on the turf. The noted plunger has never given vent to his feelings, whether winner or loser, at the racetrack. He has never been demonstrative, but has always possessed a cool, phlegmatic demeanor, which is a singular characteristic of some of the biggest turf speculators. The case of Pittsburg Phil, in some ways, resembles that of another famous plunger of his day, Michael F. Dwyer. Both of these men have won and lost thousands without showing outward signs of excitement.”
NOTE: Micheal F. Dwyer and his brother Phil Dwyer, former butchers, ran a successful racing stable and became well know for the exorbitant prices they paid for quality horses starting in the 1870s. Their huge investments paid off with major success at the track – winning the Belmont Stakes five times. They were also part of the investment group that built the Gravesend Racetrack in Coney Island, New York. Like Pittsburg Phil, Mike Dwyer’s exploits in the betting ring became legendary.
“The story has often been told of how Dwyer once made a wager of $40,000 on one of his famous racehorses and lost; he saw his horse beaten in the last jump and looking at his split second watch, cooly remarked:
“‘That was a fast run race’
Note: A $40,000 bet in 1900 equates to approximately $975,000 in 2008 dollars
“Today Dwyer is a physical wreck. He has been practically helpless for a number of years, yet he still clings to his old love. One day last summer, when he had been driven all the way from Gravesend to Morris Park, the veteran suddenly felt a desire to see the big betting ring.
“‘Take me down so that I can see the books’ he said to his faithful attendant, and forthwith they literally carried him to the scene of bustling speculation under the big grandstand. Dwyer looked at the big crowd for several moments listening to the [talk] of the layers and their runners and then turning to his attendants, said in a husky voice:
“‘I’ve seen enough! Take me back! Its the last time I shall ever go to the betting ring!’
“Pittsburg Phil has suffered fully as great a strain as Dwyer. But he has been more fortunate than the veteran horseman in that he made a fortune. Phil received a hard blow when the Jockey Club refused his entries two years ago and also revoked the license of his jockey, Willie Shaw. He protested his innocence vigorously but all to no purpose until one day last summer the stewards relented. The plunger by then was in poor health and had practically given up heavy betting. He visited the track now and then for an outing and put down a small wager out of mere force of habit but that was all. He said he could not stand the strain.”
NOTE: Phil’s involvement in the game as an owner was fought by the Jockey Club who didn’t think he would run his horses honestly considering his primary occupation as a gambler
“Men who have watched the career of these two plungers say now that if they had given vent to their feelings they would have probably escaped ill health
“‘It was inward suffering that hurt them,’ said a leading bookmaker recently. ‘They lost without a grimace and won without a smile. Other men let out a roar when they drop a bet and dance for joy when they cash and all of them are in robust health. They let off the steam which does them good. It is a fearful strain in the nerves to keep under control all the time.”
Interesting that the legend of Pittsburg Phil lauds him for keeping his cool but here the author claims it was the strain to stay calm that killed him. Phil died a month after this article was published. One year later, Dwyer died in dire circumstances because of substantial gambling losses.
Both men live in the lore of racing’s colorful era in New York before the gambling ban in 1908. They both had honors paid to them posthumously.
In 1916, a horse called George Smith, the birth name of Pittsburg Phil, won the Kentucky Derby. A book published after his death - The Maxims of Pittsburg Phil – remains in print over one hundred years later. Many of the gambling angles it articulated for the first time ring true to this day.
New York racing honored the Dwyer Brothers when they renamed the Brooklyn Handicap the Dwyer Handicap in 1918 (now known as the Dwyer Stakes).
SOURCES, NOTES, AND OBSERVATIONS
“Pittsburg Phil’s First Bet”, The Utica Journal, January 15, 1905. Accessed at Fulton History
“Phil Dwyer Dies as Suburban is Ended”, New York Times, June 19, 1917
Full-text of Tod Sloan by Himself is available at the Internet Archive
Check out previous posts about Pittsburg Phil:
Obituary of Pittsburg Phil, 1905
Pittsburg Phil Immortalized in Stone
Really enjoyed the article over at Mary Forney’s blog about lost racetracks.
Thanks for Reading and Good Luck!
Filed in Pittsburg Phil, famous gamblers, historic horseplayers, thoroughbred racing history | 8 responses so far

