The Aspirin Age: When Jack Dempsey Warred with Bill Brennan

12/14/20- Demsey- Brennan fight (Left to Right)Leo P. Flynn, Brennan Manager; Bill Brennan; Referee Haulamp; Jack Dempsey; Jack Kearns and Joe Humphries, announcer.


And after a while I wasn’t twenty-five, then not even thirty-five, and nothing was quite as good.

—F. Scott Fitzgerald


With his high-voltage style, his wrecking ball left hook, his roughneck good looks, and his mile-high Gatsbyesque rise from squalor, Jack Dempsey was at the palpitating heart of the Jazz Age sporting boom. No fighter in American history had his drawing power, and his tumultuous yet remunerative years as heavyweight champion might have inspired some of the varying lyrics of “My God, Look How the Money Rolls In.”

But Dempsey was also the last of the vaudeville champions: a man whose riches were earned beyond the ring, before mass media had evolved into an overwhelming national force predicated on hegemony, in burlesque tours, circus engagements, two-reel serials, nightclub revues, and personal appearances.

(That distinction—vaudeville champion—also meant that his title reign would be steeped in bunco. Just as James J. Corbett, Tommy Burns, and Jack Johnson had defended their titles under dubious circumstances, Dempsey would bowl over more than one challenger whose selection suggested the principles of county fairs or tent shows.)

It was a tradition set by his predecessors John L. Sullivan, Corbett, Bob Fitzsimmons, Jim Jeffries, and even Johnson, whose low Q-rating among the bigoted masses did not prevent him from drawing audiences to lectures and demonstrations of “physical culture.” (Only sawed-off Tommy Burns, whose claim to the heavyweight throne had been considered iffy, failed to capitalize on the lucrative moonlighting fad.)

After stopping a fugitive Jack Johnson in 1915, Jess Willard, as socially awkward as he was, immediately signed up to tour with Buffalo Bill and his Wild West Show. Even Hollywood called for the ungainly “Pottawatomie Giant,” who would go on to grace brittle celluloid in a short, The Heart Punch, and a full-length feature, The Challenge of Chance, which was yanked from theaters after Dempsey massacred him in Toledo. Willard, never a fan of prizefighting, made one title defense in a four-year reign that even for its time was uninspiring. When Dempsey wrenched the title away with blood-soaked mitts on July 4, 1919, his $20,000 purse looked like small change compared to the future spoils of show business. Two days after trouncing Willard, in fact, Dempsey was on the road, earning $7,500 for an appearance at an amusement park in Cincinnati and a $15,000-a-week stint on the vaudeville circuit.

In August, Dempsey would join the Sells-Floto circus for a short run as an enthusiastic part of the act, even wearing blackface for some of the musical skits. Finally, Dempsey signed a contract with Pathe Studios to star in a film serial called Daredevil Jack. “From the time I arrived in Hollywood, everyone made a big fuss over me,” he recalled in Round by Round. “My hair was wrong, and my nose was definitely wrong, so they called in Lon Chaney to do a complete overhaul. He put putty on my nose to straighten it out, puttied my ears, and penciled my brows. He put rouge on my face and goo on my head. Everyone stared when I finally walked out of the dressing room.”

This early cosmetic makeover hinted at the revamped Dempsey to come: the once-ferocious man-killer, beetle-browed, five o’clock shadow, with a permanent scowl, who would soon spend three years out of the ring and in the lush and plush fantasy worlds of sound stages and Spanish Revival mansions.

Even as Dempsey cashed in on his notoriety, however, there were rumblings about how this new heavyweight champion, a dynamo in the ring, had been unwilling to join the fight against the Central Powers in Europe. Not long after Dempsey became heavyweight champion, Grantland Rice fulminated against him in the purple prose of his era: “It would be an insult to every young American who sleeps today from Flanders to Lorraine, from the Somme to the Argonne, to crown Dempsey with any laurels built of fighting courage,” Rice wrote in the New York Tribune. “He missed the big chance of his life to prove his own manhood before his own soul.”

At a time when the Christian Temperance Union and the Anti-Saloon League were in full force, and Prohibition had just gone into effect, Dempsey was an open target for vengeful moralists. Less than a month into 1920, the whispering campaign against “The Manassa Mauler” transformed into a national clamor, and the Dempsey gravy train nearly derailed. First, several American Legion posts came out against Dempsey around the same moment the New York Times printed its own damning editorial. Then came Maxine Cates. Dempsey had married Cates in 1916 and divorced her in early 1919 before the daydream bonanza of the heavyweight title became reality. Their marriage had been a prurient one, set against the blighted backdrop of various red-light districts, and when Cates, the bordello pianist who inspired read-between-the-lines phrases in every newspaper she appeared in (“. . . she is well-known in San Francisco . . .”), joined the chorus against Dempsey, she piqued the interest of assistant U.S. attorney Charles Thomas.

On January 23, the San Francisco Chronicle printed an open letter from Cates that rocked the sporting world. In it, she charged that Dempsey, along with Jack Kearns, the steely-eyed boozer, brawler, fleecer, and finagler, had conspired to avoid the draft. “I have positive proofs in a letter in his own handwriting, naming his manager, Jack Kearns, and two others, and telling me how they succeeded in having him put in class 4A,” Cates wrote.

On February 23, a grand jury indicted Dempsey on charges of draft-dodging, and a few days later he was shockingly arrested by a U.S. Marshall. Almost immediately, Dempsey posted bail, but the negative publicity was overwhelming—and damaging.

For the next four months, Dempsey remained in a bleak holding pattern until his trial finally began on June 8, 1920, in U.S. Federal Court in San Francisco. His good fortune, which would eventually vault him from sleeping in hobo camps to visiting the White House, held up during the trial. When the letters Maxine claimed would prove that Dempsey had knowingly dodged The Great War were ruled inadmissible in court by Judge Maurice T. Dooling, the case became a battle of character. (“The indictment was largely based on thirty-five letters from Dempsey to Maxine and other western friends, which had been uncovered by federal agent O. O. Orr,” Randy Roberts wrote in his biography of Dempsey.) And the testimony of a profane hooker, one who seemed to revel in trawling the dark underbellies of Skid Row after Skid Row, was no match against the protests of the heavyweight champion of the world. No matter how sordid the jury found the Dempsey–Cates lifestyle—graphically detailed by several witnesses—or how serious the charges against him were, the benefit of the doubt would go to the celebrity with a high-powered lawyer on one side and an amoral fixer (Jack Kearns) on the other. The jury debated for ten minutes or so and returned with a verdict of not guilty.

Unlike Sacco and Vanzetti, whose trial began less than two weeks after Dempsey was acquitted, this lewd and lurid case produced no cause célèbre. The shadow of slackerdom would follow Dempsey until the next world war arrived. “During those early years after I had beaten Willard, I was probably the most cordially disliked champion that ever lived,” Dempsey recalled. Still, his acquittal had the official imprimatur of the United States government, and he resumed his career as a prizefighting celebrity.

More than a year after winning the most important title in sports, Dempsey finally entered a ring on September 6, 1920, in Benton Harbor, Michigan, to defend it. A KO of Billy Miske, not long removed from a sickbed and a few short years from dying, barely caused Dempsey to work up a sweat. For Dempsey, the ring was no place for sentiment—never mind his charitable gesture at giving Miske a desperately needed payday—and he put an end to the fight in the third round.

Another circus tour followed, his second in less than a year, and Dempsey once again enjoyed both the tomfoolery and the do-re-mi he earned as a cut-up. “I headed a show of about twenty-five wrestlers and about ten boxers for three or four weeks, grossing ninety thousand dollars, of which I got 50 percent,” Dempsey recalled in Round by Round. “That was the life. Circus people and circus camps were the friendliest of all. I joked and made up with the clowns and even attempted to put over a chimp-and-champ act, which amused children tremendously since the chimp smoked only the finest Havana cigars.”

A life of whimsy under the big top may have appealed to his impish side, but Dempsey knew that without his exploits in the ring, his marketability—along with his bankroll—would eventually dwindle. And so Dempsey and Kearns considered walkovers such as Bob Devore, Tony Mebhoir, Charlie Miller, and Georges Carpentier. In the end, they settled on “KO” Bill Brennan, a well-traveled pro who had been on the circuit since 1913.

While Dempsey staggered through the “slacker” storm, Brennan quietly mustered out of the Navy and returned to the grind, fighting wherever he could get work, from Kenosha to Syracuse to Tulsa to Cleveland to Bayonne.

Like so much of boxing during an era when prizefighting was an offshoot of carny culture, Brennan had more than a bit of flimflam in him. To begin with, his name was not Brennan. Nor was he Irish. Born Wilhelm Schenck in 1893, in Louisville, Kentucky, Brennan had already Anglicized his name once. He began his career as Bill Shanks when the war made being German a serious disadvantage both in society and in the ring. To give his career some ethnic oomph, Shanks traded his early nom de guerre for a surefire Irish identity.

During the no-decision era, when fights throughout most of the United States were often little more than exhibitions, Brennan built up an impressive record as an itinerant glove-slinger. Most of his wins came against the canvasback variety, however, although he did fare well against the aging remnants of The Great White Hopes, ramshackle bruisers such as George Rodel and Joe Bonds. High-profile fights against Harry Greb, Battling Levinsky, and Billy Miske, on the other hand, usually left Brennan on the short end.

In 1918, Brennan had been savagely stopped by Dempsey in the sixth round in Milwaukee. That fight was given a retroactive public-relations asterisk just in time for his title challenge. Throughout the buildup of the upcoming Madison Square Garden extravaganza, it had been claimed, by all parties involved, that Brennan had been unable to continue when he tweaked his ankle after suffering his umpteenth knockdown of the evening. Although contemporary newspaper accounts failed to mention this injury, they all agreed that Brennan had been rescued by a merciful referee alarmed at the mauling taking place before his eyes. Playing up a “twist of fate” angle gave looming Dempsey–Brennan clash an air of unfinished business. It was the typical boxing ballyhoo of the day, and it may have fooled Brennan himself, whose confidence belied the beating he took in the first fight. “Jack Dempsey is the one guy I can lick,” he said. “There may be other guys who can flatten me, but not Dempsey.”

The first heavyweight title fight to be held under the gleaming new Walker Law in New York, Dempsey–Brennan was set for December 14, 1920. Brennan set up camp in Providence, Rhode Island, where his chief sparring partners were Panama Joe Gans and Kid Norfolk. Dempsey operated out of New York City, where he trained on the Granite State, a battleship moored off of 96th Street and within a cab ride of Times Square. Because Billy Miske had been such a soft target, Dempsey may not have trained full-tilt, leaving him more than just rusty. Live fire was something he had not seen, realistically, since some time in 1918. In preparing for Brennan, Dempsey had other distractions as well. According to Jack Kearns, they included a hectic nightlife that undermined roadwork and sparring sessions. “Dempsey had been doing the town each night with a sleek, sophisticated divorcee” Kearns recalled in his memoir. “The lady was showing him the town. All of which turned out to have been exceedingly exhausting.”

Of course, Jack Kearns was a man whose entire life suggested what Mary McCarthy once said about her literary enemy Lillian Hellman: “Every word she writes is a lie, including ‘And’ and ‘The.’” But the fact remained that within minutes of the opening bell, it was clear that Dempsey lacked the seek-and-destroy spark that had driven him to the top.

To the shock of all who had considered Dempsey an ubermensch, Brennan, working from the perimeter, took an early lead and nearly toppled the champion in the second round with a jarring uppercut. “Had Bill seized the opportunity, the title would have changed hands then and there. For a second or two, I was helpless. That uppercut hurt me much more than the punch that knocked me out of the ring in the Firpo fight.”

From that moment on, the fight became a war of wills. Brennan worked his jab overtime and chopped at Dempsey with right crosses. Dempsey inched forward behind a crouch, hoping to draw a lead that he could counter, and aimed for the body whenever he got the chance. Round after round, they exchanged blows, with Dempsey getting the worst of it.

In the tenth, Brennan landed a slashing right that left Dempsey partially mutilated. His ear had been nearly shorn off by the blow, the kind of shot that had earned Brennan the nickname “KO” across the years. “Suddenly the whole side of my head was warm with my blood,” Dempsey recalled. “I touched my ear and it felt like it was hanging off. I was afraid that if Bill hit me with a solid punch, or even a glancing one, he might knock the ear off. I was afraid of losing my title, too, losing it in the first real test I had.”

With blood trickling down his neck, and with Brennan possibly leading on the scorecards, Dempsey became desperate and redoubled his fury over the final rounds. A last-second fusillade in the eleventh wobbled Brennan, and when the bell rang to start the twelfth, Dempsey once again exhibited that notorious killer instinct. Dempsey was one of the most devastating inside punchers in heavyweight history and when Brennan stayed close for a microsecond too long, “The Manassa Mauler” struck. “I dug a right into his solar plexus up to my wrist, and when he doubled over I got him on the ribs with a left hook that had everything I owned.”

Brennan collapsed in a heap but managed to rise just after the count of referee Johnny Haukop reached “ten.” Dempsey had salvaged his title.

When it was all over, when Dempsey staggered back to his corner, he resembled a man who had survived the Wellington disaster. His eyes were swollen, his face scraped and bruised, his lip was split, and his ear, mangled, encrusted with gore, flapped with every stutter-step. The white trunks with which he had entered the ring were now as bloody as a rag in an abattoir. And the worst of it? Dempsey knew that he was, at twenty-five, decelerating. “I was experiencing, in that fight, my first real premonition of age,” he wrote. “I felt that I was slowing up.”

Until Dempsey arrived with his slashing, frenetic offense-as-defense technique, heavyweights were merely the last remnants of Victoriana, like hansom cabs or mutoscopes. Dempsey was modernism in action, the machine age come to life, but easy living had already softened him.

From mining camp to mining camp, from hobo jungle to hobo jungle, from red-light district to red-light district—and everywhere in between—a scrawny teen brawling in sawdust bars, sometimes unable to scrape up two-bits for a meal, a weary bindlestiff alighting from boxcars under one dreary midnight moon after another, bilked anew by a promoter or manager, flimflammers to the last, now back in the subterranean, toiling by carbide lamp in the suffocating mines, then homeless for a night in Central Park, two broken ribs and a cardboard suitcase at hand, then married to a cathouse pianist, now hitting the deck against wartorn Jim Flynn in Murray, Utah (just one of those things, they said), Dempsey had become one of the merrymaking arrivistes of The Roaring Twenties.



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About Carlos Acevedo 45 Articles
Carlos Acevedo is an award-winning boxing writer and was the founder of The Cruelest Sport and is a member of the Boxing Writers Association of America. His work has appeared in Inside HBO Boxing, Undisputed Champion Network, Boxing News, Remezcla, Boxing Digest, and Esquina Boxeo.  His stories “A Darkness Made to Order” and “A Ghost Orbiting Forever” both won first place awards from the BWAA. He is a member of the International Boxing Research Organization (IBRO). Carlos is the author of Sporting Blood, published by Hamilcar Publications. Connect with Carlos on Twitter @cruelestsport.