The fierce rivalries and heated competition of high-stakes checkers.
One wintry day in March 1904, an elderly gentleman with a bushy mustache watched a dozen young railroaders squaring off at checkers boards at the Railway Y.M.C.A. at Main Street and Gerrard Street East. Invited to join in a game, the gentleman at first demurred, saying he was too out of practice, before sitting down at a board. A mere half dozen moves later, he’d roundly defeated the railroader. His disheartened opponent, determined to get even, enlisted the Y’s best checker player to face the elderly guest. Again “the veteran cleaned him up like a tramp does a lemon pie,” the Star (March 25, 1904) reported. One by one, the railroad men “went down like ninepins before the aged player’s strategy, and when the game broke up the score stood 13 wins and two draws in favor of the veteran.”
The ringer was William Fleming, a Scarborough native who for 22 years maintained an undefeated—though not undisputed—reign as the Canadian checkers champion. No mere parlour amusement in the second half of the 19th century, checkers was treated as high-stakes competition with the purse for some championship matches reaching into the hundreds of dollars—the equivalent of thousands of dollars today.
Fleming was born in Brown’s Corners—a community centred on Finch Avenue East and Markham Road—on January 21, 1841, the second youngest of nine children. His parents, Andrew and Mary Fleming, had immigrated to Scarborough from Lanarkshire, Scotland, in 1834.
(Left: Fleming’s Gravestone in St. Andrew’s Cemetery, Markham. Photo by Kevin Plummer/Torontoist.)
Andrew Fleming and his sons were among the leading sportsmen of the township, participating prominently in curling and checkers (or draughts)—an extremely popular game in the mid-19th century and taken quite seriously wherever the Scottish and English settled in North America.
Even as a child, William Fleming showed a remarkable faculty at the checkerboard. As part of a team match between players from east and west Scarborough when he was 12 years old, Fleming squared off against Adam Core, considered “the father of checker-playing in this township” in David Boyle’s The Township of Scarboro 1796-1896 (William Briggs, 1896). The teen managed to draw two of six games against the older expert, earning himself attention and credit in local checkers circles.
In the coming years, Fleming competed in the lively matches and tournaments regularly staged between clubs in Scarborough, Markham, and Toronto—the results of which were frequently published in the local press. His fellow enthusiasts might afterward discuss and analyze their checkerboard strategies while dining on oysters, but Fleming, at his young age, relied more on his raw, instinctive skill to best his opponents than studied polish. And he was successful more often than not.
In 1864, at 23 years of age, Fleming was diagnosed with a spinal disorder and confined to bed for the next three years. A school-teacher by profession, and in possession of such a keen analytical mind and mathematical acumen, Fleming passed the hours and days studying books on the great games of the past and devising solutions to checkers problems carried in newspaper columns and journals.
“He would set before his mind a definite, concrete aim and for the time being all things were laid aside which did not assist in its accomplishment,” a friend later said of Fleming’s single-minded focus and determination. “He never took hold of anything until it took hold of him, but when it did he seized it with an iron grip. When an important object was being pursued, it absorbed all his attention.” Thus schooled in the scientific side of the game, Fleming emerged from his illness with a first-rate draughts mind to go with his natural ability.
Left physically weak for the rest of his life, Fleming took as his guiding principle that “a man is never beaten until he thinks he is”—a notion undoubtedly inspired by his overcoming a long convalescence. “If William Fleming was not unconquerable,” one who knew him later recalled, “he was at least the most unconquerable man we know. No difficulty seemed sufficient to daunt him….In his contemplation of any purpose, he seemed to spend hours, even days, considering the different ways by which [any challenge] could be carried out, but the fear that it could not be done was never entertained.”
In 1867, still recuperating from his illness, Fleming took an extended, restorative trip through Ontario and Western Canada. In every town and city he passed, he sought to test himself against its best players. By his return, Fleming had lost only one, and drew 10 or 12 out of roughly 200 games.
The following year, in the fall of 1868, Fleming felt confident enough to challenge for the Canadian checkers championship. His opponent was E.R. Jacques, a Malvern resident known internationally for his “Jacques Shot” maneuver published in W.T. Call’s Vocabulary of Checkers (Schlueter Printing Co., 1909) and other volumes. Jacques, who’d played with Fleming as club teammates, was widely acknowledged as the greatest Canadian player of his time.
Decided over the course of 12 games, the Fleming-Jacques encounter was an exciting match by all accounts, with the duo’s high level of play drawing extended mention in Turf, Field and Farm and other publications. Winning three games to Jacques’ one—with eight draws—Fleming was crowned the new national champion.
“Mr. Fleming’s draughts career after this great event was one long series of successes,” reads a profile from The Draught’s World magazine. “He met all the notable players of the Dominion, and one after another invariably went under to him.” Although Fleming doesn’t seem to have travelled as widely to meet opponents as other players—believing, it seems, that challengers ought to come to his door—he out-dueled many prominent North American checkerists either in person or via telegraph.
(Left: William Fleming from Lyman Marshall Stearns’ Book of Portraits of Prominent Players, Vol. II (1895).)
In the absence of a championship tournament in Canada or an official authorizing body, claiming and contesting the national title was an informal process. The champion simply declared himself as such in the newspapers, deposited a forfeit with a third-party (to ensure the financial stakes of the contest), and awaited responses. Typically, once a challenger deposited a matching forfeit, the champion and challenger negotiated agreed-upon terms, venue, and date for the match. When Winnipeg’s Ed Kelly, champion of Manitoba, challenged Fleming to two separate matches in 1887—at $100 a side and $50 a side stakes respectively—Fleming handily vanquished his rival six games to none and six games to one.
The number of checkers enthusiasts who challenged him for the national title was so great in these years that Fleming engaged a private secretary for a time to sift through the correspondence. Like other top players, Fleming also employed a coach—Herbert Z. Wright of Boston, known as the “Wizard of the Board”—on numerous occasions to prep himself before elite matches.
Beyond the checkerboard, Fleming worked as a school teacher. After a brief stint in Owen Sound, he returned to teach at Scarborough’s S.S. #11. In 1869, he moved to Cedar Grove, a community within Markham, to teach at a newly built red-brick schoolhouse near the intersection of 14th Avenue and 10th Line (Reesor Road).
Although Fleming remained undefeated for 22 years after claiming the Canadian championship, his title was not undisputed. In about 1880, Chatham’s James Labadie declared himself Canadian champion—apparently after his challenge to play for the title went unanswered for three years—and announced his willingness to defend against all-comers. A genial and well-liked life-long bachelor, Labadie travelled widely and bested all opponents he faced that decade.
(Right: James Labadie from Lyman Marshall Stearns’ Book of Portraits of Prominent Players, Vol. II (1895).)
Fleming took exception to Labadie calling himself Canadian champion, but all attempts to schedule a match between the two fell through. First, citing patriotic sentiment, Fleming refused Labadie’s suggestion their title match be staged in Detroit, where a local club guaranteed a sizeable crowd and substantial gate receipts—perks that would be impossible, Labadie noted, in Markham Village, where Fleming now resided. Then, the two quarreled over whether travel expenses ought to reduce the size of the purse, and accused each other of failing to deposit their financial forfeits with the appropriate representatives.
“I do not care the toss of a button for the championship if it is taken from me,” Fleming proclaimed in a renewed call for challengers printed in the Turf, Field, and Farm in 1899—and carried as far afield as Auckland. “The man who takes it has to come to Markham and wrestle it from me. I will only play for the championship and the amount of stakes that it carries. I do not hold it to make money, only for the love of the game, and I will defend it against all comers, and when taken it will be by a stronger player than myself.”
Kelly responded, offering a match at $300 a side stakes. But when he was rebuffed in a disagreement over travel expenses in May 1889, he complained about Fleming in a letter to the Toronto Mail. Fleming’s swift and vitriolic response provides a glimpse into the heated rivalries the game inspired. Ordinarily a man of great self-control, he wrote:
I see Kelly again airs himself in your columns, repeating often-repeated falsehoods—falsehoods which Kelly himself and everyone who has taken interest in the matter know to be simply barefaced lies. This is the only stock-in-trade of poor Mr. Kelly; his whole composition seems to be falsehoods, bombast, and cowardice, and perhaps the poor fellow should be more pitied than blamed, as these are apparently inseparable traits of negro character.
He claimed that Kelly, afraid of facing the champion again, was “simply bluffing and thirsting for cheap newspaper notoriety.” Finally, Fleming questioned Kelly’s very skill at checkers:
There are any number of players in Ontario who can discount him every day in the week. In my two matches with him I defeated him easily…[in] perhaps the greatest defeat ever sustained by anyone in a championship match….There are dozens of players with whom I have played that can hold me much closer than this, yet this conceited creature thinks that he should rank as one of the four best players in Canada. Kelly’s fraudulent action in this matter, his barefaced lying, and his overweening conceit should place him outside the circle of all respectable checker players. I shall waste no more time on any of his correspondence.
Labadie—who cast aspersions on Fleming’s character in his own contribution to this public correspondence—likewise tried to play Fleming in 1889, but alleged that the Markham man had backed down. “I therefore hold and reclaim the honour and title of champion checker player of British North America,” Labadie concluded, “and will defend it against all comers.” Fleming maintained his claim to the title until his retirement from the game in 1890. To alleviate such disputes, the Dominion championship would eventually be organized as a formal tournament.
“Opposition had ceased!” Fleming declared in resigning the title, satisfied that’d he shown himself to be the best player and exhausted all challenges to his crown. With the demands of his business, he added, no longer permitted the practice time necessary to keep in peak form. He offered the title to several players he thought would be able to defend it, but none wanted to inherit a prize they hadn’t won by their own hand—until Kelly claimed as the last man to have faced Fleming across the draughts board. He promptly lost a championship match in Toronto in 1893 to a Mr. Forsythe of Halifax.
In his retirement from high-stakes checkers, Fleming continued to play in friendly games—like at the Railway YMCA — and continued to submit checkers problems and analyses to newspaper columns and magazines dedicated to the subject. His frequent submissions, reprinted and distributed widely for years, “were recognized as masterpieces from a great mind,” one editor recalled.
After 13 years teaching at Cedar Grove, in about 1882 he moved into Markham Village proper. He lived and operated a prosperous business at 34-36 Main Street North—a building he purchased in 1887—selling pianos, organs, and sewing machines.
Fleming’s studious attention to human nature, which had served him so well at the checker-board, also made him a shrewd salesman. On one occasion, which illustrates his sales skill and quick adaptability, Fleming and another vendor were invited to meet the purchasing committee of a church seeking an organ on the same day. “When we met,” Fleming told the Rev. E. Leslie Pidgeon, “the other fellow began to talk organ, but I tried to take in the situation with a view to finding what I had to overcome. I finally saw that there was an officious old maid, who was a music teacher in town, organist of the church, and president of the committee. The other members did not know much about organs, and what she said was likely to carry. Well, to make a long story short, the other fellow praised his organ and I praised the old maid, and I sold my organ.”
In Markham, Fleming also served as a long-time school trustee of Markham Village Public School and Markham High School, and served on the village council in addition to being active in church affairs at St. Andrew’s Presbyterian. A proponent of the Conservative Party, Fleming was a powerful and persuasive speaker—although perhaps too single-minded in his convictions to acknowledge weaknesses in his own argument or the strengths in his opponents’.
After a year of faltering health due to an intestinal condition, Fleming died at age 64 on August 8, 1905. Notices were reprinted as far afield as New Zealand, where his older brother Robert had immigrated in about 1870.
Fleming was survived by his wife Innis, his bachelor son Robert, and two daughters—one who married a Markham doctor and resided near her parents, and another who taught at the Toronto Conservatory of Music.
The granite pillar of his gravestone, to the immediate east of the entrance to St. Andrew’s Cemetery in Markham, is etched with a full-sized checkerboard, an ever-present reminder of his gift for the game that earned mention in a 1933 entry in the Ripley’s Believe It or Not series.
“William Fleming is dead, yet he liveth in the hearts of those who were dear to him,” Lyman Marshall Stearns eulogized in The Draughts Marvel and Twentieth Century Checker Compendium: A Practical Guide to Scientific Checker Playing (The Draughts Marvel Publishing Company, 1909). “He has made his last move on this earthily draughts board, and is crowned in the king row above, and who shall say that the last move was not the best, as the crowning is eternal forevermore, and his rest is peaceful and sweet.”
Other sources consulted: Home Sweet Scarborough (Scarborough Local Architectural Conservation Advisory Committee, 1996); Isabel Champion, ed., Markham 1793-1900 (Markham District Historical Museum, 1979); Gerald Redmond, The Sporting Scots of Nineteenth-century Canada (Associated University Presses, 1982); Lyman Marshall Stearns, The Draughts Marvel and Twentieth Century Checker Compendium: A Practical Guide to Scientific Checker Playing (The Draughts Marvel Publishing Company, 1909); and Stearns’ Book of Portraits of Prominent Players, Vol. II (1895); and articles from the New Zealand Herald (May 13, 1911); Toronto Daily Mail (August 22, 1883); Toronto Globe (February 20, 1883; and August 9, 1905); and the Toronto Star (April 11, 1936; and May 8, 1997).