Dan O’Leary

If God had not created Hustling Dan O’Leary, Damon Runyon would have. O’Leary is not well known today but he was well appreciated by the sportswriters of his time, as he was usually involved in something that would make an amusing story. He danced on the edge of fame and infamy, and even The National Game, one of baseball’s earliest histories, couldn’t resist telling a tale on Dan, attributed to player, manager, and later sportswriter Sam Crane. The gist of this story is that while managing in Scranton, Pennsylvania, O’Leary “motivated” his players by betting the payroll on a game. If they won, they would get their pay plus dinner and free drinks all night, but if they lost. … It’s almost needless to say his team played one of their best games ever and slaughtered the opposition. [1]

Daniel O’Leary was born on October 22, 1856, in Detroit. And he died in Chicago, at the age of 65 in 1922. These “facts,” like so many things about Dan O’Leary, are of questionable reliability. This may be because they came from a very questionable source: Hustling Dan himself. Never at a loss for a story, an angle, or a scheme, O’Leary claimed to be involved in some way in many of the important events that occurred in his lifetime.

A Daniel T. O’Leary, age 26, living in Detroit with his mother and a sister in 1880, may be our subject. If so, his mother’s name was Mary and she was a widow at the time. She and her husband were natives of Ireland. The sister’s name was Margaret T. O’Leary and her age was listed as 28.

O’Leary is reputed to have come to Chicago with the Detroit Fire Department to fight the Chicago Fire of 1871, remaining in that city afterward. [2] While it is not impossible that a firefighter of this era could have been as young as 15, it seems more likely that he was 18, lending some credibility to an 1853 birthdate. He may have claimed to be younger at some time, very possibly to further his baseball career. Detroit Engine Companies 3 and 6 traveled with their apparatus by train to the Chicago Fire. Their rigs were stuck on trains outside of town and there is some question whether they were actually able to reach the fire without their equipment.

The Detroit Historical Society has an 1871 picture of Engine Company 6 with its members identified. O’Leary is not among them. The Historical Society also has an 1871 picture of Engine Company 3 but none of the members are identified. Comparing this picture to a newspaper drawing of O’Leary that accompanies his obituary, and his height and weight statistics at baseball-reference.com, there is a member of Engine 3 who may well be O’Leary. If this is Dan, he appears to be at least 18 years old at this time.

Dan was playing ball with the Cass club of Detroit in 1876. He was elected president of the club in April 1877 and was expected to be the team’s catcher. The club planned to sell season tickets for $3 to support the effort, an undertaking that was met with skepticism as to its practicality. The team hoped to be a member of the League Alliance. [3] These plans do not appear to have materialized and by June, O’Leary was on the Minneapolis Browns team, a member of the League Alliance. The Browns finished with a record of 20 and 23 and were out of business by August 22. [4]

In 1878, O’Leary moved on to Lynn of the International Association. He played the outfield with Lynn in April and May. His next stop was Lowell, also of the International Association, where he had a brief stay, from June 4 to 6. In the June 5 game, against the Syracuse Stars, O’Leary had a hit during a five-run ninth-inning rally that led to a 7-5 come-from-behind victory for Lowell. [5]

He then played with Manchester, another International Association team, from June 7 to August 23. O’Leary’s talent for obtaining publicity showed itself while he was with Manchester. The Washington Post of July 8, 1878, reported that Dan had played in 13 games, had 19 base hits, 17 putouts and 3 assists, scored 5 runs, was left on base 10 times, and had not had an error until his 13th game. Quite a lot of coverage in a distant city for a player with limited tenure on any team. 

Dan returned to Lowell in August, and played until the end of the season in October.

In 1887, Charles “Curry” Foley, a teammate in Lowell, told how, on a trip through New York state, O’Leary had been playing poorly. Desperate, Dan asked his roommate Foley to kneel and pray with him before they left their hotel room for the ballpark in Utica. “After rising Dan said to me: — Charley, it is about time our hard luck should change.” Their luck did change and Foley recorded the following conversation O’Leary had with himself on the walk home from the park: “It is a big mistake for anyone to think that Dan O’Leary can play ball a little bit, ain’t it? Oh, yes; Oh, yes. Dan O’Leary couldn’t hit a flock of geese with a shotgun, could he? Oh, no; oh, no. It takes them fellows from Sabattisville or the town of Dungaree to hit the ball, but Dan O’Leary couldn’t hit a big balloon, could he? Oh, no; oh no. My ‘cabaser’ is out of joint and I am away on my ‘blooming chump,’ ain’t I, Charley? Oh, yes; oh, yes.” He rambled on about his qualities as a good Catholic, Paul Hines singing The Irish Washerwoman on top of the Washington Monument, Spike Brady as a hitter, Brady’s complaints about Chadwick, Caylor as a pitcher, and Anson’s fighting for his men and a suggestion that Anson be used to protect American fishermen who were complaining about a lack of protection by the US government in foreign waters, etc., etc. Back at their room, O’Leary said “Charley, infidels and (sacrilegious) people can talk as they like, but I tell you, me ‘Old Bard of Tara,’ that God is good to the Irish after all.” Dan pointed to the bed and they knelt to pray again. [6]  

The 1879 season found O’Leary with Springfield of the National Association. The International Association had changed its name after its Canadian members had withdrawn. The stop in Springfield introduced O’Leary to Sam Crane, another Springfield player who shadowed Dan during his managerial career and frequently wrote about O’Leary’s exploits after Crane retired and became a sportswriter.

While with Springfield, O’Leary played in 44 games and was tied at the end of the season for seventh in the league with a .315 batting average. [7] Newspaper coverage of Springfield from time to time highlighted his work in the outfield and at bat. On September 1, it was reported that he had been given his release. [8] On the 8th, the Springfield team folded. [9]

After leaving Springfield, O’Leary made his major-league debut on September 3, with the National League-leading Providence Grays. In seven at-bats in two games, O’Leary had three hits, drove in two runs and scored one. (Much of his career consisted of playing fewer than 10 games for his teams.) As players were frequently required to collect tickets and perform other such functions at this time, O’Leary may have already been showing his skills in the business side of baseball during his playing days.

O’Leary caught on with the Boston Red Caps of the National League in 1880, playing in three games. He returned to his hometown of Detroit in 1881 to play for the Wolverines, but played in only two games. On June 30, O’Leary struck out and dropped a fly ball in the eighth inning, which led to a Providence rally and a 7-3 victory over Detroit. [10]

One of his teammates in Detroit was Ned Hanlon, who, like O’Leary, shared a name with another famous athlete of the period. Another Dan O’Leary was a famous race walker in the 19th century, when such races were very popular. Edward “Ned” Hanlan was a Canadian who may have been the greatest individual sculler of all time. He began his career in 1874 and became the world’s professional rowing champion in London in 1880. In 1884, Dan the ballplayer bragged that he bought Hanlan his first shell, at an undisclosed time when Dan claimed to be managing a Toronto team. “Hanlan was around a good deal with the boys, and was always talking about rowing. He was a poor young fellow and had no money, but was constantly saying: ‘You mark my word, I’ll beat them all some day.’ ” Finally O’Leary and some others started a paper and raised enough to buy the ragged but ambitious young rower a shell.” [11]

If O’Leary was involved in buying Hanlan’s first shell, it would most likely have been in 1874 or earlier, as Hanlan, who was born in 1855, was rowing by the time he was 18. Even if O’Leary was born in 1853, rather than 1856, which appears likely, he would have been 21 or younger when he was managing baseball teams in Canada and buying racing sculls. Such tall tales were a frequent part of Dan’s repertoire and a famous event or person rarely popped up that Dan did not claim some connection to them. 

The Worcester Ruby Legs of the National League were Dan’s 1882 team. He appeared in six games in early June. O’Leary had limited success at bat and did even worse in the field. A June 9 report that “The Detroit Free Press call the Worcester Dan O’Leary’s nine” may have offended his teammates and management. [12] On June 13, it was noted, “O’Leary’s ancient glory as a batter seems to have departed.” [13] Tom O’Brien replaced O’Leary in the lineup.

The replacement of media darling O’Leary was condemned in the New York Clipper. “The Worcester had out their strongest pitcher and catcher, too, but by a managerial blunder the field support given the latter was marred by the presence of a mere tyro in professional playing named O’Brien, who was comparatively useless as an outfielder for strategic pitching like that of Richmond, while his play at the bat was also very poor. To replace so fine a fielder and effective a batsman as the veteran Dan O’Leary with an inexperienced amateur like O’Brien was a decided mistake. From what we can learn, however, Mr. Brown labors under the disadvantage of official interference in his business of running the team, and possibly this is a sample of the handiwork in question. If so, it accounts very plainly for the milk in the coconut of Worcester’s non-success this summer.”[14]

While Worcester was losing money that year and, along with Troy, was forced out of the National League before the next season, to be replaced by Philadelphia and New York, the loss of Dan O’Leary was hardly the cause. O’Leary’s “ancient glory as a batter” seems to be based solely on his .315 average in Springfield in 1879. While with Worcester, he had a .182 batting average and an .800 fielding average. His replacement, O’Brien, batted.202 and had a .789 fielding average as an outfielder. Neither was stellar, but it was not unreasonable for Worcester to try to improve itself by replacing an underperforming O’Leary.

O’Leary made his name as a manager in 1883 with an independent team, Indianapolis. The team struggled in early games against Detroit and Chicago of the National League. In one game, Dan’s boys seemed to be holding their own, losing 4-1 to Detroit in the seventh inning. But Detroit scored 10 runs in both the eighth and ninth innings, going on to a 24-3 victory. [15] O’Leary’s team was reported to be scheduled to play Fort Wayne under electric lights for the state championship. “The grounds will be lighted by twelve lights at the corners and sides of the grounds on poles forty feet high from the ground,” The press reported. [16]

Playing local independents and acquiring new players like former and future major leaguer Jerry Dorgan improved the team’s record and showed O’Leary’s ability to recruit quality players to Indianapolis. Other high-class players drawn to O’Leary’s banner included Jim Keenan, who had played major-league ball before 1883 and went on to a seven-year career with Cincinnati after leaving Indianapolis in 1884; John Kerins, who had a seven-year major-league career, primarily with Louisville of the American Association; Larry McKeon and John Peltz, who each had three years in the majors; And Pat Callahan, who played with Indianapolis of the American Association in 1884.

A frequent rival of Indianapolis in 1883 was the Shamrocks of Cincinnati, who played on the Reds’ grounds, usually when the major-league team was on the road. Leading up to the teams’ their first game in Cincinnati, it was reported that “the great O’Leary himself” would play and that his team “has won forty-one games out of forty-five played by them within the last two months.” [17] The Shamrocks usually won in Cincinnati and O’Leary’s team was usually victorious in Indianapolis. These games drew fairly well with over 1,000 spectators often reported. An unusual bet was made on the fourth game between the two clubs in Cincinnati. If defeated, O’Leary would have to buy 10 barrels of flour for the relief of Cincinnati’s poor, and if the Shamrocks were defeated, team president Stearns would have to do the same for the poor of Indianapolis. O’Leary again inserted himself in the lineup and, as frequently happened when he bet on his own team, Indianapolis was victorious. [18] While Dan had many flaws, his generosity to those less fortunate was frequently commented on throughout his life.

Future Hall of Famer Sam Thompson was an O’Leary discovery. Indianapolis was to play in Danville, Indiana, and the mayor of the town told O’Leary that his team could beat Dan’s if farmer Thompson could play for the home team. Interested in discovering a new talent, Dan rented a rig and he and the mayor went out to find Thompson. Sam said he’d like to play but he needed the $2.50 he was being paid for roofing. Dan paid Thompson $5 to play ball instead and Danville beat Indianapolis.Dan later claimed that he then signed Thompson to play with Indianapolis and that the next year Detroit acquired Thompson. Existing records show that Thompson went to Evansville in 1884 and was purchased by Indianapolis at the end of the ’84 season and then went to Detroit in June 1885. [19] Dan may have made the purchase from Evansville.

By the end of the 1883 season, Indianapolis was a highly respected team. The New York Herald wrote, “The Indianapolis have met with much success during the past season under the able management of Mr. Dan O’Leary, who once figured in baseball circles in this City. The Indianapolis team have done the best of any club in the west outside of the League and American Association clubs.” [20] This reference to baseball activity in New York City is one of the tantalizing hints at O’Leary’s unrecorded movements when he was not engaged as a player or manager.

The impending admittance of Indianapolis to the American Association was frequently reported on at this time. O’Leary had established a team that was about to make the transition to major-league status. But the transition back to the majors did not go smoothly for Dan. O’Leary was among the representatives of the team at the American Association meeting in Cincinnati on December 12, 1883, when the team was, as expected, admitted to the Association. [21] A month later it was reported that O’Leary had been released from Indianapolis for “expressing his mind rather plainly to a local ball player by the name of Locke, who dragged part of the conversation to one of the Directors.” [22] The report credited O’Leary for all of the success achieved by the team to date and hoped the problems between club and manager would be settled. This wish came true for a while and O’Leary was reinstated before the end of January. [23] In early February, O’Leary was the team spokesman when it challenged local ordinances banning Sunday baseball. [24]

But the hoped-for reconciliation was a thing of the past by March. “Dan O’Leary has been off and on the Indianapolis club a dozen times. Just at present he is off,” the Washington Post reported. [25] Shortly after being released, [26] O’Leary sent a telegram to the Cincinnati Union Association club “agreeing to join the nine.” [27] The American Association blacklisted O’Leary, reportedly for refusing to pay the Indianapolis club an amount under $200 the team alleged he owed. [28]

The Cincinnati team, which is now frequently called the Outlaw Reds, started strongly under O’Leary’s guidance, winning its first four games and stretching its record to 18-9 by May 30. Despite this, attendance was poor.

Cincinnati was the only Union Association team that gave any challenge to league founder Henry Lucas’s St. Louis Maroons. After an eight-game series between the two teams in which Cincinnati won only two games, O’Leary was replaced as manager by Sam Crane. Lack of discipline and leadership, with reports of O’Leary drinking with his players and betting on their games, were blamed for his dismissal. [29] O’Leary’s final record as manager was 20-15. Sam Crane added 49 wins against only 21 losses and the Outlaw Reds finished second to St. Louis. A tale from this period illustrates management’s concern with O’Leary. After a game Dan “sent a small boy out for a pitcher of beer. Meantime the president of the club arrived on the scene. When the boy returned Dan poured the beer over the boy, saying, ‘The next time I send you for milk, get it.’ ” [30]

In later life O’Leary claimed to have had a hand in the downfall of the Union Association by “going over to the Cleveland club of the National League and taking some stars with him.” [31] Henry Lucas bought the Cleveland club in order to make room for his Maroons in the National League, and Cleveland manager Charlie Hackett took key players with him to Brooklyn.

By August, the Indianapolis team of the American Association was trying to get O’Leary removed from the blacklist. [32] No one seems to have been able to stay mad at Dan for very long. O’Leary returned to National Agreement baseball in 1885 as manager of Toledo of the Western League.

By March 18, O’Leary had raised subscriptions for all but $450 of the amount required to finance his team. He expressed his confidence in Toledo as a baseball town and in the community leaders’ willingness to invest in his effort. The local correspondent endorsed this effort. [33]

O’Leary bet Cleveland manager Tom Lawrence a suit of clothes that Cleveland would not win more than three of their first eight-game series between the teams. It was also reported that Dan had taken up roller-skating. [34] Later in the season, Dan and some of the Toledo team were involved in a baseball game on skates against the Milwaukee team. There was a close relationship between the Cleveland and Toledo franchises from the start. O’Leary represented both clubs at a schedule committee meeting in St. Louis on March 27. [35]

As his team solidified, Dan expressed his confidence: “Dan O’Leary of the Toledos says he wants the Western League pennant, and Ted Sullivan of the Kansas City (and president of the Western League) retorts that the only way he can get it is to steal it. The Toledo uniform was also reported on, being cadet gray pants and shirt, blue socks, and a gray cap with a blue band. [36]

There were frequent reports of O’Leary and team President W.H. Cook signing quality players. The Toledo team was thought to be a strong nine but in need of some seasoning as the pennant race began. Around this time Dan was credited with giving Silver Flint his nickname. It was thought to have been a play on Flint’s middle name, Sylvester. [37] O’Leary also gave his team its nickname, the Avengers. 

There continued to be reports of new signings right up until the end of May. Despite this, by June 7 Toledo had managed a record of only 8-21. Cleveland at 13-16 had disbanded and Keokuk had replaced Omaha on June 6. With its close rival gone, Toledo itself disbanded on June 11. The players were good enough that other teams quickly picked up most of them. [38]

O’Leary was not as lucky as his players. He returned to his home in Detroit after the Toledo club ceased operations, lamenting that there was “nothing left of the Toledo club save the debts. They are more substantial then ever. Sunk $8,000 on the season. Best season I ever saw – for losing money. Had a nice time in Toledo. Town very attached to me – attachment awaiting me on every corner.” [39]

In late March of 1886, O’Leary was in Elmira, New York, bearing plans for a professional baseball club. All the citizens had to do was raise $2,500 for stock in the team, and O’Leary promised to buy $500 of those shares.

Early efforts to sell stock resulted in a number of subscriptions being taken and even some of the stock being paid for in cash. With these funds, O’Leary headed to New York City in mid-April to hire players. Although it was late in the season to be organizing a baseball team, O’Leary was quite successful in signing impressive players for a small-city team. Among the more familiar players on the team were Frank Devin, Eddie Kennedy, Grayson S. “Gracie” Pierce, and John “Dasher” Troy. Devin pitched for Baltimore of the American Association in 1883 and finished 1886 with New York of the National League. Kennedy was one of the original independent Metropolitans of 1880 and stayed with the team through their move to the American Association in 1883, then joined Elmira in 1886. He returned to the majors at the end of the 1886 season with Brooklyn of the Association. Pierce had spent time with Louisville, Baltimore, and Columbus of the American Association, went over to New York of the National League, and then returned to the Association with the New York Metropolitans in 1884. Troy played with Detroit, Providence, and New York of the National League before joining the Metropolitans for 1884 and 1885.

The easy availability of so many players from the Metropolitans may have been in part due to the speculation between the 1885 and 1886 seasons that the American Association was going to expel the Metropolitans because of problems with John B. Day’s ownership of both the National League and American Association New York franchises.

In Pennsylvania, the Williamsport Grit reported that local people were promoting the formation of a Pennsylvania State Association. On April 28, it was cheerfully reported in Elmira that O’Leary had secured the league’s Scranton franchise.

By May 5, the Scranton area was under the impression that the Elmira team had been moved to Scranton. In Elmira they were under the impression that the Elmira team was only playing under the Scranton name in Pennsylvania, and that O’Leary would soon develop a separate Scranton team and their Elmiras would return to playing exclusively for their city. O’Leary explained the need to sign the players to contracts under the Scranton name as a necessity because any player who broke a state league contract could be blacklisted, while the independent status of Elmira left him without such protection.

During mid-May, O’Leary pressured Scranton-area supporters to provide his team with adequate playing grounds. He whetted the appetite of the Scranton fans with the thing they desired most, a series of victories over neighboring Wilkes-Barre. O’Leary’s team was seen as so superior to their main Pennsylvania State Association rival that Wilkes-Barre would have to recruit a whole new team to hope to match it.

The Elmira papers reported these games, although what was called the Scranton team in Pennsylvania was referred to as the Elmira team in New York. It was also reported in Scranton and Elmira that the team would play its next three games in the New York community. Scranton fans were reassured that as soon as suitable grounds were provided, the team would play its league championship games in the Pennsylvania city.

On May 24, O’Leary’s first monthly financial statement to his Elmira backers was hailed as an example of good management, and the local citizens were told that the success of their team rested solely on their willingness to support it. At the end of May, O’Leary secured grounds off Providence Road in Scranton from the Delaware, Lackawanna & Western Railroad that he planned to fit out as a ballfield.

Meanwhile, back in New York, the team was still referred to as the Elmiras, but the inability of being able to identify the next date on which they would play in that city was beginning to become a concern. Despite this, O’Leary’s Elmira supporters expressed their thanks to Scranton for providing another source of income and support for O’Leary’s efforts so that the manager’s undertakings might be profitable, a shared team apparently being preferred to no team at all.

The term “O’Leary’s Indians” was also beginning to be used in Pennsylvania to identify the team; similar to the way the Elmira press began to distance the community from the team.

Difficulties with the players began to surface. There were reports that Captain Troy had resigned, with Kennedy, a native of nearby Carbondale, expected as his replacement. Troy did not follow through with his plan and maintained his position for a time.

A bright spot of the period was the naming by the Grit newspaper of an all-star team based on batting that included five Scranton players. They were Bagley at catcher, Helfer at first, Troy at second, and Waters and Brill in the outfield. The good team O’Leary had promised both cities was there, but some of the manager’s practices were beginning to wear thin with players, stockholders, and fans on both sides of the state border.

O’Leary’s need for funds was the reason given for a July Fourth weekend that included an exhibition game in Wilkes-Barre on Saturday, two games in the Brooklyn area on Sunday, a train trip from there back to Scranton, another train trip and a game in Wilkes-Barre on Monday morning and a return trip to Scranton and another game with Wilkes-Barre in the afternoon. When both championship games with Wilkes-Barre were lost, Scranton fans felt misused and Troy, Kennedy, and Diven demanded their release, which they were granted. Helfer also tried to resign but O’Leary refused his request. O’Leary blamed the Scranton club’s directors for his problems with his players, making a bad situation worse and leading to the president of the club calling the manager a liar in print. The situation was defused somewhat when Troy and Kennedy changed their minds and returned to the team. Criticism surrounding this incident was strong in both cities but Elmira’s feelings against O’Leary were expressed more bitterly in local coverage. By July 11, the statement was printed, “Elmira no longer has a ball club.” [40]  

The team continued to win games but was struggling. Criticism of team discipline and the condition of the players began to circulate more regularly. On July 24, the roof caved in on O’Leary. He could pay neither his room and office rent nor his players, and the landlord seized the bats and other available assets of the club. The Scranton club directors fired O’Leary and the “O’Learys” disbanded. The Scranton directors were successful in getting the State Association to accept a new team they formed without O’Leary and to allow it to pick up where the old team left off. Sam Crane became manager of the Scranton team in 1888.

The Elmira Telegram of August 1 printed a scathing yet accurate article regarding O’Leary’s adventures in Scranton and Elmira. The paper took a bow for its earlier warnings against O’Leary. It also reported that O’Leary and his assistant in this adventure, Dave Wheeler, “had a set-to with a woman of ‘fairy’ reputation” [41] who assaulted both men.

On August 22, reports begin to appear of O’Leary’s arrest in New York City on a warrant sworn out by an Elmira landlord. O’Leary was taken back to Elmira to settle the debt after failing to raise the needed funds from his New York City friends. The reluctant landlord accepted $40 plus O’Leary’s watch and overcoat after it became apparent that other Elmira creditors with superior lien positions were about to secure warrants against him. The “Hustler” was left enough money for train fare to New York and left the upstate community in a hurry.

After the Elmira-Scranton fiasco, O’Leary was expected to be managing in New Orleans in 1887. This turned out to be a theatrical troupe. As Dan was frequently at liberty during the baseball season, his theatrical adventures may have sustained him both during and after the season. Also during 1887, he arranged a benefit for the Irish Land League. It did not have the desired results and Dan complained, “So help me ginger, if you would have fired a gatling gun through the house last night you wouldn’t have hit a Fenian” [42] Later in life he continued to frequent the theater and give other theatrical managers both wanted and unwanted advice.

O’Leary’s baseball and theatrical careers were soon replaced by a new undertaking. Starting around 1887, O’Leary became a free-lance police reporter in Chicago’s Twenty-First Ward. He was owner and sole employee of the O’Leary News Bureau at the East Chicago Avenue police station. He continued in this work until his death 35 years later. He may have tried his hand at both baseball and theater productions later in life but this is evidenced only in offhand comments in articles reminiscing about his earlier adventures. One example is a picture of O’Leary in the uniform of a team called the Pittsburgh Browns listed in the SABR Baseball Encyclopedia. There is also a story about O’Leary running the bases the wrong way that is sometimes said to have happened when he was playing with this Pittsburgh team in 1883, although ’83 is one of the rare years when Dan seems to have been employed by the same team for an entire season.

O’Leary was a baseball camp follower throughout his life. He arranged a benefit for Fred Pfeffer in 1897. Dan did it up in grand style with a one-hour concert before a baseball game with the Chicago fire chief umpiring. In the game, old-time players including Cherokee Fisher, Ross Barnes, and Dick Higham faced a theatrical group from a production of Jack and the Beanstalk. After the game, “the Marquettes and the Unions, the two strongest City league teams, will come on for a championship game, with Fred Pfeffer umpiring.” [43]

Dan was included in an article on “the immortals of the game” that included references to Cap Anson and Tim Murnane and lamented the absence of Ted Sullivan, his old Western League opponent, at the event. In the article, O’Leary discussed the trademark carnation in his lapel. At this point, he was referred to more often as Carnation Dan than as Hustling Dan. A newspaper article said he wore the carnation in memory of a sister who had died. He said, “Sometimes I think I was responsible for the beloved (President) McKinley’s adoption of the carnation.” He said they had met at Cincinnati’s Gibson Hotel in 1884 and McKinley had commented that he thought wearing a carnation in the lapel was a beautiful idea and began wearing one himself. Admirers during this period were wearing carnations on the assassinated president’s birthday in his memory. [44]

In 1920, a couple of years before he died, O’Leary made news by commenting on the Black Sox scandal while standing outside the grand jury room. He was quoted as saying the players “can throw away their shoes and they know it.” [45] He was one of the early members of Chicago’s long-lived Old Timers’ Baseball Association, participating in reunions alongside the likes of Anson, Pfeffer, and Al Spink. At the time of Anson’s death in April 1922, O’Leary was listed along with Tom Foley and Frank Keefer as the group’s representatives at the funeral services. [46]

Dan did not last long after Anson. In mid-June of 1922, articles appeared about his hospitalization with heart problems. On June 24, he succumbed to “gastritis complicated by heart weakness” at St’ Joseph’s Hospital in Chicago. His pallbearers were newspapermen he had worked with, and his estate, consisting of $600 and personal items, was handled by Chicago Tribune reporter Clem Manning. O’Leary is buried in Mount Carmel Cemetery in Chicago. [47]

The sister for whom Dan wore his carnation had taken care of his widowed mother and Dan had taken care of them financially. They remained in Detroit. Once when he was younger, Dan had lost at the races while visiting Detroit and needed a loan from his sister. At the bank where he went to cash her check, a teller asked Dan for identification. Dan responded, “By the jump-up holy Judas Iscariot, is there a man in Detroit who don’t know Dan O’Leary?” The teller at the adjoining window responded “I never saw him in all my life, but that’s Dan all right.” [48]

Later in 1922, another sister died. Apparently realizing early in life that praying for Dan would be a full-time job, this sister had become a nun in the Society of St. Vincent de Paul in St. Louis. She had risen to be a mother superior before being stricken with paralysis five years before her death. [49]

Dan O’Leary was one of the true characters of the early days of professional baseball. Part player, part manager/general manager, and part conman, possibly from time to time by necessity, Hustling Dan grew to be forgiven and loved by most as Carnation Dan, and was admired at the time of his death for his generosity and lifelong friendships with people from all walks of life.


[1] Alfred H. Spink, The National Game, 2nd Ed. Carbondale and Edwardsville: Southern Illinois University Press, 2000, p.250.

[2] “Carnation Dan,” Reporter at 69, Fights For Life. Chicago Tribune, June 16, 1922.

[3] Chicago Tribune, April 22, 1877.

[4] Chicago Inter Ocean, August 22, 1877.

[5] Boston Globe, June 6, 1878.

[6] Sporting Life, February 9, 1887.

[7]Spalding’s Base Ball Guide, 1880

[8] Springfield Republican, September 1, 1879.

[9] Springfield Republican, September 9, 1879.

[10] Chicago Inter Ocean, July 1, 1881.

[11] Washington Post, July 13, 1884.

[12] Worcester Daily Spy, June 9, 1882.

[13] Worcester Daily Spy, June 13, 1882.

[14] New York Clipper as reported in Worcester Daily Spy, June 23, 1882.

[15] Cincinnati Commercial Tribune, April 20, 1883.

[16] San Francisco Bulletin, May 28, 1883.

[17] Cincinnati Commercial Tribune, July 15, 1883.

[18] Cincinnati Commercial Tribune, September 16, 1883.

[19] “Dan O’Leary Tells How He Discovered Big Sam Thompson,” undated article from unidentified source, in collection of information compiled by the Thompson family and SABR BioProject Biography of Sam Thompson by Don Thompson

[20] New York Herald, October 15, 1883.

[21] New York Herald, December 13, 1883.

[22] Cincinnati Commercial Tribune, January 13, 1884.

[23] Springfield Republican, January 24, 1884.

[24] Washington Post, February 17, 1884.

[25] Washington Post, March 16, 1883.

[26] Springfield Republican, March 9, 1884.

[27] New York Times, March 18, 1884.

[28] Springfield Republican, April 6, 1884.

[29] www.cincysports.net/OutlawReds.htm

[30] Chicago Daily Tribune, June 29, 1922.

[31] Chicago Daily Tribune, June 25, 1922.

[32] Boston Daily Globe, August 24, 1884.

[33] Cleveland Plain Dealer, March 19, 1885.

[34] Cleveland Plain Dealer, March 25, 1885.

[35] Cleveland Plain Dealer, March 27, 1885.

[36] Cleveland Plain Dealer, April 17, 1885.

[37] Cleveland Plain Dealer, April 28, 1885.

[38] Macon Weekly Telegraph, June 14, 1885.

[39] Cleveland Plain Dealer, June 30, 1885.

[40] Sporting Life, quoted in Elmira Morning Telegram, July 7, 1886.

[41] Elmira Morning Telegram, August 1, 1886.

[42] Unidentified clipping, May 18, 1887, in O’Leary’s Hall of Fame file

[43] Chicago Daily Tribune, September 19, 1897.

[44] Unidentified clipping, October 20, 1906, in O’Leary’s Hall of Fame file

[45] Chicago Daily Tribune, October 5, 1920.

[46] Chicago Daily Tribune, April 16, 1922.

[47] Chicago Daily Tribune, June 25, 1922.

[48] Unidentified clipping, January 14, 1905, in O’Leary’s Hall of Fame file

[49] Chicago Daily Tribune, December 31, 1922.

(Many of the papers listed were searched through www.GenealogyBank.com or www.proquest.com )


Johnson, Lloyd, and Miles Wolff, Editors. The Encyclopedia of Minor League Baseball, Third Edition. Durham, NC: Baseball America, Inc., 2007.

Nemec, David. The Great Encyclopedia of 19th Century Major League Baseball. New York: Donald I. Fine Books, Penguin Books USA Inc., 1997.

Petula, Nicholas E. A History of Scranton Professional Baseball 1865-1953. Scranton, PA: Self-published, 1989.

White, Sol. (Introduction by Jerry Malloy). Sol White’s History of Colored Base Ball with other documents of the early Black game, 1886-1936. Lincoln and London: University of Nebraska Press, 1995.

Boston Daily Globe, April 1886 to June 1886.

Carbondale (PA) Leader, May 1886 to October 1886.

Elmira Daily Advertiser, March 1886 to August 1886.

Elmira Morning Telegram, April 1886 to August 1886.

Scranton Daily Republican, May 1886 to September 1886.

Scranton Weekly Republican, May 1886 to October 1886.

The Sporting News, March 1886 to October 1886.

Williamsport Grit, February 1886 to January 1887.




SABR 19cbb@yahoogroups.com

Detroit Fire Department History at www.ci.detroit.mi.us

Detroit Historical Society November 2009 e-mails and pictures.

O’Leary Hall of Fame file.

Special Thanks to: Richard Hershberger for his input on early leagues; Joel Stone of the Detroit Historical Society for information on the 1871 Detroit Fire Department; Don Thompson for information on O’Leary and Sam Thompson; David Ball for information on the 1883 Indianapolis team.

Full Name

Daniel O'Leary


October 22, 1856 at Detroit, MI (USA)


June 24, 1922 at Chicago, IL (USA)

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