Ollie O’Mara gambled that he was good enough to play baseball professionally – leaving his family in St. Louis to try his hand at playing for Scrappy Bill Joyce in Missoula, Montana.  Early in his career – before leg and ankle injuries sapped him of his speed – Ollie was a gambler on the base paths.  He would gamble most springs that a hold out might lead to bigger contracts.  He kept taking chances to improve his lot – ditching a minor league team for a chance to earn money playing outlaw baseball in Pennsylvania and again in the Midwest League playing in Racine and Kenosha.  He gambled on himself by starting his own business and then by integrating himself into a world of Chicago gamblers.  Finally, when his lifetime of gambling got the best of him, he disappeared.  For more than 15 years.

Oliver Edward O’Mara was born to William O’Mara and Mary (Bartley) O’Mara on 08 March 1891.  William was a second generation Irish immigrant.  Mary’s father was born in Massachusetts but her mother was born in Ireland.  Years later, Oliver would join the Sons of Erin, a social group dedicated to Irish heritage.  William was a teamster, but he also spent a lot of years working as a stable foreman.  Oliver was the fifth of seven children – which meant that Mary was busy caring for a large and active family.

Oliver only completed the fifth grade – but he was a bright, energetic, and motivated boy.  Raised in the Kerry Patch district of St. Louis, his was a rough and tumble life.  He once broke a leg jumping off a lumber pile, and he would get in fights.  One fight resulted in his breaking a knuckle (the other kid was also hospitalized), but the finger wasn’t set right, so they broke it a second time.  Ollie was also a reckless and aggressive athlete who played baseball in the St. Louis Trolley League as a kid and was coached by St. Louis Browns scout Charley Barrett.

Old time Brooklyn ball players remember him as a red headed pest, who used to hang around the grounds of the St. Louis Cardinals and chase flies. In those days the visiting teams used to ride to the grounds in buses, something now utterly beneath the dignity of the high-priced athletes. Hitching on behind the buses and making jeering remarks about the inmates was one of the cherished traditions of the town boy, and a persistent hitcher was O’Mara. He was on the step of the Brooklyn bus one day and indulging in a particularly fine flow of comment about the visitors, when one of them firmly, and not at all gently, grabbed him by the scruff of the neck and dropped him upon the highway. Dusting himself off the kid yelled at the Superbas:

“Yah, yer big stiffs. I’ll be up there some day in the big league, when you guys are in the bush again!”

Rice. “Ollie O’Mara is Once Again A Signed And Sealed Superba” The Brooklyn Daily Eagle, 04 March 1918, Page 8.

In 1911, he got his first shot playing for a team in Missoula, MT under Scrappy Bill Joyce.  According to local sources, he was still a bit raw – aggressive in the field and on the base paths, but didn’t hit much.  Joyce decided to go in a different direction and released O’Mara who was hitting just .226 in 22 games.  Undeterred, O’Mara found a team a bit closer to home in Hannibal, MO.  Playing for Jake Beckley, the “speedy Cannibal shortstop” was especially solid in the field and was so confident in his ability that he was a hold out at the beginning of the 1912 season.

“O’Mara tended to that territory last season in great fashion and several Central Association managers said he was the fastest and most sensational shortstop in the league. Ollie’s hitting was not up to the standard. However the midget swatted the horsehide…there was a fielder under the ball most all the time. O’Mara expects a change of luck next season. His highest ambition is the big leagues which he expects to enter in a few years…

“Two Hold Outs Join The Ranks”, Daily Gate City, 20 February 1912, Page 7.

In weeks after the season started, O’Mara started hitting, too.  He swatted a ball off a Bull Durham sign in Ottumwa, IA, winning 1440 packages of cigarettes.  Originally hitting in the seventh or eighth spot, he now was batting near the top of the order – and instead of playing second base, he was the regular shortstop.  As if his meteoric rise in a low level minor league wasn’t enough – at the end of the 1912 season, Hughie Jennings called him to Detroit to get a look with the Tigers.

“The biggest thrill I got was when I joined the Detroit ballclub in 1912,” O’Mara remembered.  “I’d been dreaming of the major leagues, and I was just thrilled to be there, especially on the same team as Ty Cobb.

“I remember seeing Cobb right after they farmed me out. He saw me carrying my bag when I was coming down the steps. All he said was, ‘you’ll be back.'”

Robinson, Dave. “Ollie O’Mara Remembers Cobb, Stengel – Old Timer Knew ’em All”, Nevada State Journal, 11 September 1975, Page 7.

The Tigers maintained his rights but let him go after letting him play one game – but let him choose between heading to Providence for a couple of weeks or heading home.  Ollie went home for the winter, but back to Providence for the spring of 1913.  He didn’t last long – though, Providence farmed him to Durham, but Ollie was so good there Providence called him back.  His second chance at Providence was a disaster – hitting just .235 and making an error every ten chances he lost his nerve and got discouraged and wound up jumping the team.  However, he later apologized for his rash behavior and Patsy Donovan, the Providence manager, agreed to dispatch O’Mara to Evansville, Indiana.

O’Mara found his way in Evansville – in one game he handled thirteen chances cleanly but apparently wasn’t always in the good graces of the Evansville fans.  One assumes that the fiery O’Mara didn’t take this sort of thing kindly – but he played well enough for Providence to take him back for a few days.  It didn’t work – Providence traded him to a team in Fort Wayne, Indiana.  There, the chip on Ollie’s shoulder as big as ever, he got to play against his old Evansville teammates and put on a show.  He scored three runs, including smashing a homer.  He showed speed on the paths – O’Mara was known for taking wide turns around first base and regularly trying to draw throws or race into second base.  And, he fielded his position perfectly.

“…Ollie is always on the jump, taking frightful leads off the bases and always trying to tempt a catcher or an infielder to make a shot to drive him back.”

“Gets Real Dash Into Play in Bases”, Fort Wayne Journal-Gazette, 27 August 1913, Page 6.

O’Mara, whose season was blurred by poor play, nerves, and bouts of anger mixed in with moments of exciting play and unusual quickness in the field and on the bases, suddenly was drafted a second time – this time by Brooklyn.  This came as a surprise to some, including Fort Wayne writers, who noted, “However, it’s surely possible that in a year’s time he will have developed so that he will be fit for the big league. At any rate the fans will closely watch his work with the Brooklyn club next spring.”

1914, the Federal League was competing with the National and American League for talent.  So, even though Brooklyn held O’Mara’s rights, he was not necessarily a lock to sign a contract.

Essentially a tale of how serious the salary war is – Wilbert Robinson has to travel to St. Louis and meet with O’Mara out of fear he will go to join Pittsburgh. After O’Mara says he’s been keeping in good shape and running a pool room in St. Louis, Robinson asks O’Mara if he had received any contracts from Federal League teams. O’Mara admits he has – from Pittsburgh – and actually shows the contract to Robinson, who agrees to match the contract and warns O’Mara not to jump. In the imagined conversation, Robinson tells O’Mara. It would be a very grave mistake for you to do anything rash, such as jumping. I know what it means, as I have been through the thing myself. You may jump and get a little more money for awhile, but in the end you will have to come back to organized baseball and a salary in accordance with your playing ability.

O’Mara signed with Brooklyn.

“Are Big Leaguers Worried? Listen To This Conversation”, Nashville Tennessean, 17 January 1914, Page 10.

It took a little while for Wilbert Robinson to warm to the idea, but finally in June he put O’Mara’s name in the lineup as a regular shortstop.  He continued his fine play through the summer, earning a two-year contract extension.  O’Mara was hitting .263 with 14 stolen bases when his luck ran out.

O’Mara scratched a hit to Martin in the first inning and was sacrificed to second by Daubert. He played off second and Rixey undertook to catch him napping. O’ Mara ran between Martin and the throw in such a clever manner that he confused Martin, who let the ball go through his legs to center field, O’Mara promptly hustling to third.

Wheat lifted a fly to Becker in medium short center. It would have been folly for any other member of the team to have tried to score, but O’Mara is so fast and is so shifty in his sliding that he was sent home on what proved to be a costly gamble. Becker made a good throw to the plate and O’Mara arrived almost exactly with the ball, but he was blocked by Billy Killifer, and had not yet touched the rubber.

O’Mara started to slide. As he hit the dirt his spikes hung him, and, in addition to that jolt, his left leg brought up heavily against Killifer’s shinguard. His impetus carried him around and beyond Killifer, but, as he came into the catcher, the breaking of the bones in O’Mara’s left leg could be heard distinctly far above in the press stand. The sound was remarkably clear and was exactly that of breaking a small, dry stick sharply over the knee.

… Physicians carried him from the field; he was taken to St. Mary’s Hospital… treated by Dr. Kennedy, who predicted that, because of O’Mara’s youth and clean living, he would experience no permanent ill effects from the injury.

Rice. “O’Mara Breaks Leg In Worst Game Ebbets Field Ever Saw”, Brooklyn Daily Eagle, 15 August 1914, Page 14.

If O’Mara wasn’t going to feel permanent ill effects, it surely must have felt like it as when he was still using crutches in November.  Usually he played basketball in the winter – this winter he watched from the sidelines.  “(I) feel like an old man to have to sit on the bench and watch the fellows tear around the floor having the time of their lives, ” O’Mara told a wire service reporter in January.   His ankle wasn’t healing even though the break in his leg healed correctly.  And his frustration got the best of him when out on a date.

“Ollie O’Mara, shortstop of the Brooklyn Nationals, whose home is in St. Louis knocked the head of a street car motorman through a car window last evening, and when he appeared in court today the United Railways Company refused to prosecute him. He was allowed to go in a hurry, too, when he said he was in a rush for a conference with President Ebbets of the Dodgers, who was in the city.

“O’Mara told the police that he was on his way to a theater with a young woman. When the car stopped to wait for a faulty switch to open the motorman, Richard O’Connell, refused to open the door and let them out. O’Connell, according to O’Mara, struck at him when he insisted.

“‘Then,’ remarked Ollie, ‘I got mad and poked his head through the glass.’

“O’Connell, who showed signs that it was some poke, admitted that he had refused to open the door until the switch would work and he could pull up to the regular stopping place. The motorman is a rabid fan and when he learned whom O’Mara was he shook hands with him in court.

“Dodger’s Infielder Becomes Real Rough”, Washington Times, 28 January 1915, Page 12.

Wonder what his date thought of the incident?  To Ollie, it may not have mattered – he was popular with the fairer sex when a ballplayer.  “The Dodger home attendance perked up wonderfully last spring while Ollie was cavorting on the green and quite a bulky portion of the increased patronage came from the shy, sweet maidens that blossom in Brooklyn,” told a wire copy article.  That same article said that while he was laid up in the hospital after his injury, he received a number of visits from his female fans.

O’Mara still had some influence with Brooklyn as a player, too.  He helped arrange a meeting between Charles Ebbets and Casey Stengel that allowed Brooklyn to keep their star outfielder and avoid having him leave for Kansas City or Chicago in the Federal League.  Ollie would retain a good friendship with Stengel over the years and tell stories about Stengel for the rest of his days.

When spring training began for the 1915 season, O’Mara was still favoring his leg.  In time, the shortstop would play second base – until it was obvious he wasn’t mobile enough to play there either.  O’Mara would settle in and play a number of games at third base, too.  Two other things were keeping Ollie from being a better baseball player.  He thought he was a much more accomplished player than he really was – and he couldn’t keep his anger and emotions in check.  In one case, he chose to argue with an umpire when he had actually bunted a ball in fair territory.

Coombs opened the third inning for Brooklyn with a single to left. He moved to second on a single to right by Hi Myers. O’Mara laid down a bunted third strike, and the bunt was fair.

Then comes a difference of opinion and statements. Hank O’Day was umpiring behind the plate, and says he did not declare O’Mara was out. O’Mara persists that Hank did call him out. Anyhow, Ollie ran half way to first base, became convinced that Hank had done him a great wrong, and turned back to talk it over with Hank – an utterly foolish task.

Meanwhile, Charley Dooin had picked up the ball and thrown to third to snag Coombs, which was a simple little manner on its face, but Charles’ throw was wild, going to left, and costing Charles one error. In left field the unusually competent and expedition George Burns let the ball go through his legs for an error. The combined circumstances allowed Coombs and Myers to score, and bring us back to O’Mara.

Ollie, thinking he had been wrought a great injury by H. O’Day, was bent on arguing with that placid personage. He did not get far. He was grabbed by Ivan Olson, who took a firm hold on the shoulders and ears of the shortstop and sought to shoot him to first, willy nilly. Ollie refused to be shot. He preferred to talk. To help Ollie get next to himself, three other athletes joined Olson, who was now in a berserker rage, and against the Irish root and branch. Ivan grabbed Ollie by the neck and gave him a kick in the pants and also in the general direction of first base, telling him that he was safe and to keep going when the going was good. Ollie kept going – back to H. O’Day, where the going was extremely bad. He pulled himself out the clutches of our irate Scandanavian and was hurtling toward O’Day, when a relay from Burns to Hans Lobert to Brainard put him out at first, which relay set a new mark in the peculiarities and uncertainties of the pastime.

Rice. “Beating the Giants Becoming Habit”, Brooklyn Daily Eagle, 14 August 1915, Page 14.

His decline in play and his problematic behavior eventually led to his release to the minors.  After hitting .263 prior to breaking his leg in 1914, his average fell to .244 in 1915 and .202 in 1916.  For 1917, he was dispatched to Atlanta in the Southern Association, where he played well enough at shortstop to earn one more shot with Brooklyn in 1918.  He now wintered in Brooklyn, having married Mabel V. Kearney, and was working in a naval shipyard when he received his contract.  The war effort was attracting ballplayers, including O’Mara, and some were paid better there than on the field.  Writers knew, however, that O’Mara was fortunate that his old team had openings and held out hope that he had outgrown some of his immature behavior.

Ollie’s future depends upon whether he will be able to play as well at Ebbets Field as he plays at other fields. Many baseball performers shine only with the support of the home town fans, while others are oppressed with the feeling at home that they must do something extraordinary every little minute to keep up their reputation with the folks who know them by their first names, and who make coarse comments upon how they part their hair. O’Mara belonged in years gone by to the latter class, but his is considerably older now than he was when he first came to Brooklyn as one of the freshest kids in captivity in 1914. If he has acquired steadiness with age he should be a great comfort to Flatbush and environs, and the reports of his doings in Atlanta are all to that effect.

Rice. “Ollie O’Mara is Once Again A Signed And Sealed Superba” The Brooklyn Daily Eagle, 04 March 1918, Page 8.

O’Mara didn’t hit well in 1918 and his fate was sealed.  A pay cut for 1919 didn’t make Ollie happy either and Brooklyn was more than happy to pull their contract offer and waive him.  By early 1919, he was released to Oakland, which didn’t work out, and then Indianapolis in the American Association, which did.  Chatting up a veteran hitter, he was told to stop guessing what kind of pitch would be thrown.  Instead, he would look for a curve ball figuring he could catch up to fastballs. In 1919, O’Mara would hit .340 and started the 1920 season hitting .381.  O’Mara figured he would be given another chance in the majors, but that never happened.  Instead, in 1920, he jumped to an outlaw independent league in the Pennsylvania oil country.  As O’Mara later explained, “…it was a bunch of rich oil men who wanted to have baseball teams for a while.”

Being an outlaw suited O’Mara.  Teams were formed in Oil City and Franklin, PA.  A bunch of major leaguers took the money and ran, guys like Doc Wise, Mike Cantwell, Steve Yerkes and even George Sisler (briefly).  When that league ran out of gas, he played in another outlaw league – the Midwest League.  This league operated in the early 1920s in the smaller cities around Chicago, including teams in Racine and Kenosha.  Others who played in this league were Dick Kerr, Bert Gallia, Jim (Hippo) Vaughn, and Frank and Bob Roth.

Over time, Ollie missed playing in professional baseball and wanted to prove that he could still play.  Repeatedly he asked to be reinstated and eventually, in 1928, he was allowed to be a utility player for Milwaukee in the American Association.  He only played in about a dozen games, but he hit. 270 in his limited action.  And then, his professional baseball life was over.  He’d stay active in baseball, but in the amateur ranks of his new home city.

Ollie O’Mara was an established business man in Kenosha, Wisconsin, frequently working with his brother, John.  He ran a billiard parlor with his wife, Mabel, and they raised six kids – three sons and three daughters.  They lived a comfortable life, involved in the community in many ways, for the next two decades.

Soon after becoming a senator in 1948, Tennessee Democrat Estes Kefauver was put in charge of a committee to investigate organized crime.  His committee aggressively went after major gambling and crime families of all shapes and sizes, and brought down the politicians who enabled or ignored the actions of organized crime in their cities and states.  When going after a bunch of the crime families of Chicago, the investigations turned to satellite organizations in Kenosha and Racine.  A key witness in one investigation was John O’Mara, Ollie’s brother.  In July, 1950, four coordinated raids hit the Lake Shore Restaurant, the Kenosha Athletic Club, Ebner’s Place, and the Brunswick Billiards parlor – the last one operated by Ollie O’Mara.

John O’Mara apparently told everything – laying out the history of gambling in Kenosha since 1935, and included liquor distribution and a bunch of bribes paid to the city council president, Felix Olkives, a city councilman named Howard Coates, and the police chief, Stanley Haukedahl.  Bribes were used to help influence votes on parking meter installations, city manager votes, and looking the other way in terms of gambling.  In addition to charges brought against Olkives, Coates and Haukedahl, the sheriff, Leonard Jenson, was also indicted for bribery and perjury, while the district attorney, Urban J. Zievers, was tagged for neglect of duty.  Though it was never explained, John O’Mara had a falling out with Ollie prior to his initial meetings with the Kefauver committee in 1950 – and he turned on his brother and his associates.

The three gamblers called out were George Ebner, Frank “Ditchy” Greco, and Ollie O’Mara.  Each were indicted for bribery and bookmaking (Ollie was also indicted for maintaining an illegal race track wire service) – but only Ebner turned himself in.  He was arraigned and set free on $8500 bond after pleading innocent.  Greco briefly went into hiding, saying he spent nine months working for the Merchant Marine.  Eventually, however, he turned himself in.  Ollie O’Mara was first rumored to have been hiding in Chicago.  Then he was gone.  When asked about the whereabouts of his brother, John O’Mara said, “So many people are missing nowadays.”  Ollie was never located.  Another arrest warrant went after Ollie’s son, James, who was arrested in Racine for gambling charges.  The court system processed everyone involved – except Oliver O’Mara.

Years passed.  In 1966, more than fifteen years later, a reporter for the Milwaukee Journal followed some leads and found Ollie O’Mara living in Las Vegas.  He also interviewed Ollie – and then reported this information to then Sheriff-elect William P. Schmitt.  Schmitt explained that the warrants were still active and the charges were still valid.  However, so much time had passed O’Mara’s lawyers were able to get charges dismissed claiming that the prosecution had abandoned the case years ago.  Ollie was never brought before a judge; he was allowed to continue to live his life in Las Vegas.  He had been protected by gambling interests there in part because he used to provide protection for Chicago gamblers in his past.  After a few years, he moved in with his son Bill, a lawyer in Reno.

In retirement, Ollie liked to watch and talk about baseball (usually telling stories about Casey Stengel) and he spent afternoons making modest bets on horse racing and ball games.  Barry Halper reached out to O’Mara, and O’Mara was able to help Halper acquire uniforms worn by O’Mara, Dan Brouthers, Hughie Jennings, Willie Keeler, Wilbert Robinson, and Joe Kelley, among others.  In 1981, Ollie was invited to throw out the first pitch on Opening Day for the Los Angeles Dodgers.  He celebrated his 90th birthday with a large family party.

Ollie continued his active retirement until passing away on 24 October 1989.  At 98, he was the second oldest living player at the time of his death.  Ollie had cheated the odds and cheated the law – but he couldn’t cheat death.

SOURCES:

New York Marriage License
Nevada Death Records
1870 US Census
1880 US Census
1900 US Census
1910 US Census
1915 New York Census
1920 US Census
1930 US Census
1940 US Census
WWII Registration Card
Baseball-Reference.com
FindaGrave.com

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