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Philadelphia Jack O’Brien: The Master Puzzler

By Mike Casey

Our perception of famous people can sometimes be cruel and misplaced, often fashioned by the hasty and not always reliable yardstick of gut instinct.

Boxers are a special case in point, since boxing itself is a harsh and basically primitive practice. Whatever our social background and lifestyle, we tend to share a fairly uniform idea of how a fighting man should look and behave. While some of us might wince at the stereotype image of Rocky Balboa, we don’t want our ideal man to be an effete intellectual who constantly wrestles with the morality of his profession at uptown dinner parties with the local intelligentsia.

Boxers are not supposed to be quite that smart. Nor do we care for too many layers of pious self-servitude or fake modesty.

Gene Tunney, an undisputed wizard of the ring, was never going to click with the blue collar crowd with his love of art, literature and high society. Sugar Ray Leonard, who perfected the half-startled look of Bambi-like innocence, made Roberto Duran’s blood boil long before they met in the ring. Floyd Mayweather Jnr, for all his admirable skill, has a similar effect on just about everyone.

Ray ‘Boom Boom’ Mancini had all the right working class credentials but then made the mistake of writing a toe-curling poem in honour of his dad Lennie, fuelling the desire of many to lock young Ray away in a Youngstown steel mill.

You get the picture. First impressions, often formed in our impressionable and impatient youth, can be difficult to erase.

But what of those fighters who fall between the stalls and muddy the picture still further by throwing shadows at us? One would have to search long and hard to find a more confusing or contradictory member of that school than the brilliantly gifted Quaker, Philadelphia Jack O’Brien.

For here was a dashingly handsome conundrum indeed. O’Brien was intelligent, erudite and almost stately in his general demeanour. He was also a wonderful boxer whose sublime skills were allied to great toughness and courage. Out of his boxing togs, Philadelphia Jack could have passed for a politician, a man of letters or a tennis-playing dandy of infuriating talent. But O’Brien always had that certain hard glint in his eye, that tantalising whiff of danger that follows some men around. The daring and adventurous streak in his blood meant that he could cope equally well on both sides of the street.

Historian Tracy Callis, who studies the fighters of the past at great length, holds a special place in his heart for O’Brien. Tracy says of Jack: “He was a smart, heady fighter who had excellent quickness of hands and feet. He was not a slugger but a master boxer, a ring genius who teased his adversaries and lured them into off-balanced and vulnerable positions. His footwork was commendable and his head movement superb, enabling him to slip most punches sent his way.

“Jack never weighed much more than a middleweight but fought light-heavyweights and heavyweights often, winning the light-heavyweight championship of the world along the way. He began fighting in December of 1896 and had lost only two official battles going into his April 1905 bout against Hugo Kelly. This was O’Brien’s 139th fight, although some sources contend he had lost for the third time during March 1904, in his 123rd bout.

“He dodged no one and fought all worthy opponents, black and white. In a career of nearly 180 bouts, O’Brien lost but six official contests (some sources report seven losses). In the process, he defeated such men as Bob Fitzsimmons, Tommy Burns, Joe Choynski, Al Kaufman, Charles McKeever, Jack (Twin) Sullivan, Joe Butler, Young Peter Jackson, George Cole, Tom Tracey, Frank Craig, Al Neil, Billy Stift, Mike Schreck and Kid Carter.”

O’Brien’s positive influence also extended beyond the ring, as Tracy Callis points out: “Due to his personal conduct and social standing, O’Brien was a tremendous ambassador for boxing. Jack had as his friends some of the socially prominent men in Philadelphia, who considered him a fine character and a man of very good influence in the community.

“O’Brien had a taste for the rough and rowdy. He took care of himself well and mixed it up splendidly in the ring.

“But he appreciated the finer things in life too. He dressed well, played the violin, frequented the symphony and opera and associated with the social elite of Philadelphia. His private life was exemplary too. Anthony J Drexel Biddle and other men of high distinction considered O’Brien to be their friend.”

In the ring, Philadelphia Jack O’Brien was never loved like Sam Langford or lionised like Stanley Ketchel. Indeed, many writers enjoyed poking gentle fun at Jack. Much like Tunney, who in many ways was O’Brien’s cerebral successor, Jack just happened to carry an unfortunately superior air about him. It was a great source of gratification to many when an earthy fellow like Ketchel belted O’Brien flush and mussed his nice hair.

Respect, however, carries far more weight than popular appeal, and Philadelphia Jack O’Brien commanded huge respect as one of the great masters of the roped square.

Then he did something quite remarkable that threw his entire career under the microscope. In 1907, two years after winning the light-heavyweight championship from the great but ageing Bob Fitzsimmons, O’Brien signed a written statement in which he declared that nearly all his fights were faked. The statement was published in a San Francisco newspaper and naturally hit many fight fans with all the dizzying force of a cleverly tossed curve ball.

Faked or fixed? That was the big question, for, as we know, there can be a subtle but big difference between the two. We should remember too that Philadelphia Jack was well known for his sense of humour and his love of an elaborate joke, most especially when it came to baiting members of the fourth estate.

As boxing writer Dan Daniel noted some years later: “As Philadelphia Jack had as many as 180 fights, he must have perpetrated the most colossal series of barnies yet charged to any fighter since the boys wielded the cestus in the Coliseum in Rome.

“The odd feature of the O’Brien confession was that it did not mark his retirement from the ring. As a matter of fact, he never quit. Death came to Jack on November 12, 1942, after an operation in New York, thirty years after he had climbed through the ropes for the last time.

“When O’Brien issued that signed confession of fakery on a grand scale, the suspicions aroused by quite a few of his fights were confirmed. But some of the matches he listed as barnies fooled even the experts.”

Dan Daniel went on to pose some pertinent questions: “Why did O’Brien issue that startling statement? How much of it was based on truth and how much on his hatred of Tommy Burns, whom he named as a fellow conspirator who had given him the double cross?”



O’Brien twice challenged Burns for the heavyweight championship, both fights being staged at the Naud Junction Pavilion in Los Angeles. In November 1906, Burns drew with Jack over 20 rounds in a match refereed by former champion, Jim Jeffries.

O’Brien had no quarrel with that verdict, although there was more than the odd whiff about the fight itself. Jack’s weight for that fight is nearly always listed as 163lbs in today’s records, but it was more likely the 153lbs claimed by Dan Daniel and other contemporaries. Burns, at 172lbs, would have therefore had a significant weight advantage. It is important to remember that the diminutive Burns, who was really a natural middleweight like Jack, was an exceptionally fine fighter whose achievements in the heavyweight class were worthy of much praise. Tommy was a terrific puncher for his weight, and while the challengers to his throne were not of the most sterling quality, his star has really only diminished in recent years. He was fast, foxy and very dangerous.

But it was the second match with Burns that so chafed with O’Brien. Tommy won a 20-rounds decision, but according to Jack, that wasn’t the way it was meant to go!

“Jack insisted that the second fight was to have been a swindle,” wrote Dan Daniel. “He also called his fights with Peter Jackson, Tommy Ryan, Bob Fitzsimmons, Joe Walcott and Sam Berger plain fakes.”

O’Brien was indeed the master puzzler. For how do we define that word ‘fake’ in his case? He was plainly a boxer of outstanding talent and world class, a middleweight who masqueraded as a light-heavyweight and heavyweight and beat some of the finest fighters of the age. At thirty-one years of age and near the end of the trail, the masterful Jack was still able to give the prime Stanley Ketchel the fight of his life and very nearly beat him in their classic first match in New York. Two years after that and virtually fighting from memory, O’Brien displayed exemplary courage and skill before being swept under by the young tiger that was Sam Langford.

Were all of Jack’s wins fixed or faked? Of course they weren’t. O’Brien was a very intelligent man with a clever and inventive mind, but he would have held a top job with the government if he had been able to hoodwink the enemy on such a grand scale.

God alone knows why Jack issued his off-the-wall declaration, but Sam Berger was one man who took exception to the charge after fighting a six-rounds no-contest with O’Brien in Jack’s hometown of Philadelphia in 1906.

According to O’Brien, that fight was so rigged that he and Sam had rehearsed their moves the night before in a barn. Berger was furious and issued a statement of his own in which he slammed Jack as ‘a lying, conceited ass’.

Here was what Sam had to say: “I will allow the fight in Philadelphia to speak for itself. The representatives of the New York press who witnessed the contest proclaimed the fight one of the fiercest ever seen in the East.

“Jawn (Jack) O’Brien had to visit the hospital to have his eyes stitched, and at the conclusion of our bout could hardly stand and was covered with blood from head to foot.

“It is certain that if it was necessary for O’Brien to take this punishment in order to perpetrate a fake, he would be more inclined to fight on the square.”

Well, according to ringsiders, Jack was never so hapless that he was bleeding from head to foot. But the fight with Berger certainly seemed to be a genuine and hard fought battle.


Walcott and Fitzsimmons 

Far more odious were Philadelphia Jack’s curious affairs with Barbados Joe Walcott and Bob Fitzsimmons. Walcott, as a black man, was far more philosophical about the shenanigans of his era and saw little reason to be shy about them when probed.

After a highly suspicious and none too taxing dance with Philadelphia Jack at the Grand Dime theatre in Boston in 1903, Walcott told reporters, “I could have knocked Jack out any time I wanted but I had an agreement with him that he would last ten rounds and I kept it.”

Those who had witnessed the event might have been tempted to say, “No kidding.”

The scene was set when referee Rube Waddell, a celebrated pitcher for the Philadelphia Athletics, declared that he would call the fight a draw if both fighters were on their feet at the conclusion. “What the Rube knew about boxing,” wrote Dan Daniel, “could have been stuffed into a small pill box.”

Daniel insisted that O’Brien’s victory over Fitzsimmons for Bob’s light-heavyweight championship had been marked down as a fake long before Jack issued his shocking admission.

A Philadelphia newspaper explained the curious terms of the fight: “O’Brien insisted that the articles prohibited fighting in clinches. All he had to do was to lead at Fitz and, whether or not he landed the punch, grab hold. Fitzsimmons thus was prevented from punching back at short range.”

As Dan Daniel asked: “Whoever heard of articles barring punching in clinching? In short, the fight with Fitz was checked off as a fake long before O’Brien came out with his confession of multiple swindles.”

These are fair and sound points, although it should be noted that Bob, a true killer of the ring from any range right into his fistic dotage, later admitted that he simply couldn’t trap the clever O’Brien. When asked by a friend if he had hurt his hands in the fight, Fitz replied, “’Ow could I ‘urt them? I never ‘it ‘im!”

As ever in this life, it all depends on how you see it. Eddie Smith, an excellent boxing writer of the era, was well familiar with Philadelphia Jack’s chicanery and acknowledged it as a permanent black mark against the skilful Quaker.

Yet Smith wrote: “Philadelphia Jack O’Brien is one of the fastest workmen in the ring today, a lightning striker for fair when started, and his clean-cut work with Bob Fitzsimmons and Al Kaufman will go down in history with the best exhibitions ever seen in San Francisco.”

Dan Daniel, who was a close friend of Nat Fleischer, wrote for The Ring magazine for decades and established an equally fine reputation as a baseball writer and expert. Not lightly did Mr Daniel lay into the heroes of his day.

Yet he was quite scathing in his ultimate summation of Philadelphia Jack O’Brien, albeit greatly respectful of Jack’s undoubted ability and greatness as a fighter.

“In short, O’Brien was the arch ring faker of all time. Let nothing be taken away from him as a clever, crafty boxer. When he was levelling, he was a great scrapper to watch.

“O’Brien is cited as one of the horrible examples of our old-time ring heroes by Jim Jacobs, who has been showing excerpts from old fight films to prove his contention that the top-rated fighters of the long ago were bums.

“Jacobs must have picked some of Jack’s shady appearances to demonstrate the fistic fashions of the long ago.

“Looking over O’Brien’s long record, you wonder which of his fights were the real things.

“When he gave out that confession of wholesale fakery, O’Brien’s friends defended him with the statement that he was so far superior to the vast majority of his opponents that he had to make ‘arrangements’ in order to lure them into the ring.

“Let it be said that this was plain bunk. He was a man who lasted a long time in the ring, made a lot of money in it, and, but for his confession, would have gone into the history of the roped arena as a great fighter and grand benefactor of boxing.”

This is tough and bitter medicine indeed for fans of Philadelphia Jack O’Brien to swallow. Yet is the case against Jack really as cut and dried as that?

Tracy Callis has never believed so, maintaining that O’Brien’s intelligence and clever wit were never truly understood by many and therefore often misconstrued. There was another mischievous trait to Jack’s character. Far from dreading adverse criticism, he seemed to embrace it and relish it in much the same way as a challenging foe.

“Jack liked to tease with newspaper reporters as much as he liked to toy with foes in the ring,” explains Tracy Callis. “He made a number of statements during his career that were clearly incorrect and never seemed to worry about their impact, such as drawing ‘the color line’ on his future opponents and then proceeding to fight several blacks, and of course mentioning ‘fixed’ bouts he engaged in. When interrogated by writers, he said all of his contests were rigged. They were fixed all right, in the sense that the verdict was set – victories for O’Brien due to his dazzling skills.”

Like so many other fighters of his time, O’Brien is something of a lost and neglected soul in the modern age due to the lack of hard evidence in his favour. Today’s fans want to see a film. They want to see a DVD. That is not entirely their fault. Many have never known any other way of judging fighters and don’t particularly care for learning new tricks. Tell them to seek out books and original newspaper articles and they will baulk at the task of having to take a trip to the local library.

Limited film of Philadelphia Jack O’Brien is certainly available, but of very poor quality. Movie techniques were in their stumbling infancy and unable to cope with ever shifting action.



On this subject, Tracy Callis says: “The most negative comments about O’Brien involve the film clip of his first title fight with Tommy Burns in which Jack was on the run for most of the available footage, and his two fights with Stanley Ketchel. O’Brien finished flat on his back in the first of those fights and suffered a quick knockout loss in the second. Let us consider these points.

“To begin with, the film footage in the first Burns bout is limited and only parts of the contest are shown. From this bit of film, it can be seen that O’Brien actually jogged around the ring to avoid Burns. Not only did Jack trot around the ring, but he did a turnaround, circled in front of Burns, moved away and threw some punches.

“In addition to using his fast feet and quick hands in the usual fighting manner, Jack often did a number of antics in the ring to disrupt a foe’s rhythm, including jumping up into the air and hopping around at times. But, all in all, he was mobile and possessed very fast hands with good power in his blows. Even in the Burns clip, it can be seen how he was agile, light on his feet and limber in throwing punches.”

Tracy Callis quite rightly praises O’Brien for his heroic stand against the fearsome Stanley Ketchel in the first of their two duels, which Jack came within seconds of winning. Ketchel, in typical storybook fashion, knocked O’Brien unconscious with eight seconds left on the clock after a ferocious, last-gasp offensive.

“It must be remembered that many men lost to Ketchel, an all-time great, and ended up on their backs staring at the ceiling. Most of these fellows were outgunned from the very start of the fight, even in their primes.

“With O’Brien, it was different. He fought Ketchel near the end of his career when Jack’s skills were fading. Yet he schooled Ketchel brilliantly for most of the first contest, finally wearing down before Stanley’s onslaught.

“One account of this fight reports that Jack was two pounds over the agreed weight limit and that Willus Britt, Ketchel’s manager, said there would be no fight if O’Brien failed to lose the extra weight. So Jack immediately worked out – vigorously – lost the two pounds and boxed the contest.

“Shortly afterwards, in the second fight, the older O’Brien’s eroded skills were exposed and accounted for his quick loss in three rounds.”


O’Brien’s All-Time Ranking 

Tracy Callis believes that the high all-time ranking accorded to O’Brien by the more knowledgeable of boxing people confirms that Philadelphia Jack was indeed the real deal as a fighter even if a fair number of his fights were not the real deal at all!

Says Tracy: “Nat Loubet (former Ring editor) called Jack the number one all-time light-heavyweight. Billy McCarney also rated O’Brien number one, while Nat Fleischer and Laurence Fielding had him at number two. Charley Rose had Jack at number three, while writer John McCallum, who conducted a poll of old-time fight men, listed O’Brien at number four. Dan Cuoco, director of the International Boxing Research Organization (IBRO) sees Jack as the fifth best light-heavyweight.

“As one popular sportswriter of O’Brien’s time wrote, ‘He was equalled by few and excelled by none’.

“I concur and rank O’Brien as the number five all-time light-heavyweight, the number three all-time middleweight and the number nine all-time pound-for-pound fighter in boxing history.”

So how good really was crafty old Jack when he played it straight? Well, he was good enough to give the mighty Jack Johnson a very uncomfortable time in their heavyweight championship fight in the spring of 1909, which, somewhat strangely is rarely discussed. Let it be noted too that this bout was sandwiched between the Ketchel fights when O’Brien was indisputably on the slide.

The contest with Johnson proved to be a terrific draw for the National Athletic Club in Philadelphia. Fans poured in from New York, Boston, Baltimore, Washington, Pittsburgh and Chicago. The arena, which could house a crowd of 4,000, was full by eight o’clock in the evening, with box seats selling at ten dollars apiece.

Did Johnson take the bout seriously? There is every indication that he did and Jack was certainly as sharp as ever when it came to the business side of the promotion. He demanded his $5,000 cash guarantee immediately when he drove up to the arena in his big automobile. No five grand, said Jack, no fight. He told the management that he was in prime condition and that O’Brien would be given no chance to display his best form.

Jack was actually a little fleshy at 205lbs, while O’Brien looked superbly fit at 162 ˝. Stanley Ketchel got the crowd in the right mood when he was introduced to the ring to a thunderous ovation.

What transpired in the six-rounds fight surprised a lot of people. The following morning, the headline in the Syracuse Daily Herald read: O’BRIEN OUTCLASSES JOHNSON EXCEPT IN PHYSICAL STRENGTH.

The report that followed ran thus: “Jack Johnson, champion heavyweight of the world, did not cover himself with glory in his six-round bout with Philadelphia Jack O’Brien at the National AC here last night.

“The big Negro was outpunched by a small margin in a fight that was fast and interesting all the way. Johnson was as slow as cold molasses in getting after the fleet Quaker, and all his punches, when they landed, lacked championship power.

“He had many chances to show his strength but boxed like a second rater and missed countless opportunities. O’Brien, who was fully 40 pounds lighter, did much of the forcing. He landed nine clean blows and showed a greater knowledge of ring tactics.

“He made Johnson look foolish with his clever feinting and in every way appeared the master, except in point of physical strength.”

This, then, was Philadelphia Jack O’Brien. A master puzzler, a constant conundrum. You pay your money and you take your choice when assessing his overall standing in boxing history. Arch faker or misunderstood genius? In Jack’s case, the answer would appear to be a tantalising and befuddling combination of both!



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