Heralded in the Milwaukee Sentinel a few years earlier as a noted "poet, philosopher, former pug and barkeeper," Cornelius J. "Con" O'Leary was 60 years old when his life turned on a dime in 1918.
It was a counterfeit dime. O'Leary made it following directions in a book he found at the Milwaukee Public Library. He gave the slug to a kid hawking newspapers at the intersection of what are now West Wisconsin and North Plankinton Avenues. Two months later, a judge gave O'Leary three years in the federal pen at Leavenworth, Kansas, for the crime of "uttering and passing counterfeit coin."
It wasn't O'Leary's first transgression. The native of Ontario, Canada came to Milwaukee in 1889 to break the law by participating in a prizefight. Wisconsin had one of the strictest statutes against prizefighting in the country, adopted in 1878 on the ground that the spectacle of two men bashing each other with their fists did, in the words of late 19th century Governor George Peck, "more harm to the young people who are growing up ... than most anything I know of" by promoting the notion that "it is not a very serious thing to kill a man if you have eight-ounce gloves on."
Actually, for most of his fights when O'Leary wore gloves at all they were skintight ones with no padding. And most of the bouts lasted until he or the other guy was too beat up to continue.
"O'Leary was one of the best known of the famous bare knuckle fighters who were popular here in the outlaw days of boxing in Wisconsin," wrote J.A. Ermatinger of the Journal in 1918. "Some of his fights were desperate affairs and they usually went to a finish."
In one of them Con knocked his opponent out in less than a minute, and then proceeded to knock him out four more times, with two-minute intervals, to give the audience its money's worth. When they resumed fighting after the third knockout, the other guy landed a wild haymaker that knocked O'Leary out, and upon his revival they went at it again until Con was finally proclaimed the winner.
He was 16 and studying to become a priest when O'Leary saw his first fight and switched vocations on the spot. His longest bout was against Alphonse LaFontaine in Montreal. It lasted 39 rounds. O'Leary won, and shortly afterwards he migrated to Milwaukee.
To prevent interference from the police, fights were held in private, their locations leaked only to members of "The Push," as followers of boxing were then known. When O'Leary earned $100 by knocking out Jack Hayes in 11 rounds on Jan. 14, 1891, the action started at 2:45 a.m. "way down the line at a secluded old road house beyond the outskirts of the town," according to the Journal. O'Leary won the Wisconsin lightweight championship in 1893 by knocking out Doc Malory in six rounds "in a barn near Layton Park."
He was known as the "Knight of the Uppercut" because that was Con's signature punch – "My money-getter," he called it. "There are scores of men who use the uppercut, but it's only once in a hundred times that a fighter gets it home," he said in 1901. "They feint their opponent open and then swing in the uppercut when he is going away from them. That's why they miss. An uppercut should be used on a fighter when he is coming to you. Then it is pretty sure to land and it gives you two good chances. You can probably catch your man over the heart, and as he doubles up from the blow you can slide up and catch him on the jaw. With a man coming to you, it's a great blow, but when he is getting away it is a waste of strength."
Con was still fighting then, in his mid-40s. Boxing, while still officially illegal, was intermittently permitted at the turn of the century by local authorities as long as padded gloves were worn and the number of rounds was limited. O'Leary sneered at such wussifications of the Manly Art.
"Why, these fellows nowadays are not fighters," he said. "If they ever got into a real fight with any of the old timers, they would not know what to do. They jump into a ring and wrestle around for six or ten rounds and draw $500 or $1,000. I'll bet you if one ever got into a ring not knowing whether the fight was going to last six, 10 or 50 rounds, only knowing that he had to knock out his opponent or be knocked out himself, you'd have to build a fence around the ring to keep him in."
When he finally quit fighting O'Leary became a door-to-door peddler – he preferred the loftier term "commission merchant" – and then opened a downtown boxing school. He called himself "Professor Con. O'Leary" and was a renowned character about town dishing out blarney as handily as he used to dish out uppercuts. In 1905, Professor O'Leary's photo and testimonial appeared in advertisements for Stuart's Dyspepsia Tablets, guaranteed to "make thin, nervous dyspeptic people strong, plump and well."
He frequently carried on feuds with rival boxing managers and fans via long-winded missives to the newspapers. After someone criticized an O'Leary-trained fighter in a letter, Con scored a literary KO by replying that if the writer's "brains were dynamite and somebody touched a match to them, the explosion would not blow the hat off the top of his head."
The Professor was also a popular bartender at downtown gin mills, and never required much prompting to reminisce about the grand old days of pugilism before the girly-men took it over; or, in verse he penned himself, extol practitioners of the sport for which he gave up the priesthood as holy men in their own right:
Excuse me, you frown on the boxer;
You think him a loafer, a tough –
A chap that's without education,
Not even a gem in the rough.
But in that you're entirely mistaken –
In the breast of the boxer there beats
A heart that is bigger and broader
Than some men's you meet on the streets...
Where'er goes the glove of the boxer
There vanish the pistol and knife,
Men rely on the weapons of nature
And a premium's placed upon life.
That's why I am in the profession –
No doubt there are some who will blame,
But a gentleman can be a boxer
For boxing's a gentleman's game.
Who knows what possessed the celebrated Knight of the Uppercut to give counterfeiting a whirl. One story suggested it was just his "mechanical turn of mind." Or maybe he was broke. In 1915, O'Leary was diagnosed with tuberculosis, had an abscess carved out of a lung and dropped down to about 100 lbs. After that he largely dropped out of public notice until the front-page news J.A. Ermatinger called "a shock to the many acquaintances of the famous old boxer."
"Speed up my change, I'm in a hurry," O'Leary nervously told newsie Rubin Plotkin after handing over his homemade dime for a paper that day in December 1918. Then he walked a ways down the street, stopped at an alley and tossed the newspaper away without having even glanced at it. His odd behavior was a red flag to young Plotkin, who looked closer at the dime O'Leary gave him and then looked for the nearest cop.
At the trial, O'Leary's lawyer pleaded for mercy on the grounds that with his lung problems Con "wouldn't last six months" in prison and that he "was the idol of his friends."
"A man who cheats boys who are trying to make an honest living is not deserving of leniency," declared Federal Judge Ferdinand Geiger before sentencing the old Professor to his three-year stretch.
O'Leary entered Leavenworth Prison on Feb. 19, 1919, listing his occupation as "Physical Culture Director." It wasn't TB but VD that turned out to be his biggest medical concern, and Inmate #13660 received twice-weekly injections of mercury, the then-common treatment for syphilis.
On May 17, 1920, President Woodrow Wilson paroled O'Leary after letters of recommendation came from U.S. Rep. John Kleczka, Capt. of Detectives John T. Sullivan and Judge Geiger himself, among others.
"I always found (O'Leary) to be upright, honest and energetic," wrote Milwaukee Comptroller Louis Kotecki. "I was shocked to hear that he had been sentenced to Leavenworth, Kansas, as I never thought he would be guilty of any wrongdoing."
Back home, Milwaukee's once voluble poet-philosopher worked under the radar as a salesman and clerk. City directories have listings for O'Leary at 246 8th St. until 1926, after which he either died or once more went way down the line beyond the outskirts of the town.
