A Biography of North Omaha’s Ollie William Jackson

Ollie Jackson (1865-1934), North Omaha, Nebraska

The life of a “notorious negro police character” who was an “alleged dopester” that spent many years in “Class A” among Omaha’s “underworld elements” makes for good reading. Living at North 24th and Burdette, he was known as a pimp, a stickup man, a drug dealer, a gambler, and “the moving spirit of a pool room in the tenderloin district” who was also a lieutenant for the city’s crime boss Tom Dennison. This is a biography of North Omaha’s Ollie W. Jackson.

Becoming Notorious

Omaha, Nebraska 1890s
This was Ollie Jackson’s Omaha, looking north up N. 17th Street in the 1890’s. Within view would have been brothels, saloons, gambling houses, and other criminal enterprises he was likely tied up in. Pic courtesy of History Nebraska.

I can’t find where Ollie William Jackson was born in 1865, but regardless of where he was from, he was a man about Omaha. His name was regularly in the Omaha World-Herald, the Omaha Bee, the Omaha Monitor, and later, the Omaha Guide. He was associated with crimes of all kinds, including shootings, muggings, and more. Following are some of the stories I found with him in them.

As early as 1885, Jackson was implicated in crimes by the city’s newspapers. That year the Omaha Bee said he’d been arrested under suspicion of burglarizing a saloon downtown. One of four men to be arrested, the newspapers didn’t report the outcomes of the arrests.

In a detailed 1898 feature, the Omaha World-Herald referred to him as “the moving spirit of a pool room in the tenderloin district, and bondsman (limited).” In the feature, entitled “Men of Influence,” Jackson was said to be one of a “trio of colored habitues who lend dignity and style to Omaha’s police court and help draw attention to it.” Along with Vic Walker and Chase Green, Jackson regularly “perched his feet on the table, smoking rare cigarettes and Havanas” and mystified the newspaper reporter, who wrote glowingly about the men’s presence. The newspaper opined that the work of these men in court regularly led to, “the old sweet song, ‘I’ll discharge you this time, but don’t come in here again. I’ll give you thirty days on bread and water the next time.”‘

That same year, Jackson presided over a formal “colored Republican” gathering at Nate Brown’s restaurant at N. 12th and Capitol Avenue. Other luminaries from the Black community included Dr. Matthew Ricketts.

Constant Arrests

Omaha pool hall 1910
This is a 1910 image of a pool hall on Farnam Street in downtown Omaha. Courtesy of the Durham Museum.

Throughout the first decade of the 1900s, Jackson was the longtime janitor of the Omaha jail.

In 1903, Jackson was at the Midway when another Black man was shot. Implicated in telephoning a wagon to take the wounded man to the hospital, there were no additional notes about his role in the event. In 1906, he was arrested for on the charge of “being a suspicious character.” Attributed as “a well known colored character,” he was said to regularly “get friends out of jail.”

Jackson was arrested in 1909 for being part of a robbery while a woman “entertained” a customer. A man named Charles Falco from Reno, Nevada, had $2,000 stolen from him while he was “at the room of a colored woman” named Quedella Robinson. After the money went missing, Jackson voluntarily returned $800 to the police department and was promptly arrested. Jackson was eventually charged with receiving a $1,000 bill Robinson stole from Falco; he posted bail and there’s no further story, except that the remainder of the money was never recovered.

For many years between the mid-1900s and 1921, Jackson ran a real estate business at 2426 Lake Street. Likely a front for his other activities, he apparently retired that year and sold his business to someone else.

In the late 1910s, Ollie Jackson was one of the highest paid Black employees on the City of Omaha payroll. making $1,152 annually, its unknown what his job was. However, its important to note that he was hired by Mayor Jim Dahlman, a seven-time mayor who was controlled by Tom Dennison. So if Ollie Jackson was working for Dennison, he had a good salary to get the job done.

In April 1920, Jackson was arrested by the Omaha Police Department after shooting two men. Apparently there was a fight between Jackson and six men, including four white men and two Black men. The four white men had been harassing Jackson when they attacked him on a packed streetcar. None of the attackers were apparently arrested. Three of the men were reported as drunk, and the Omaha Bee reported that the shooting caused a “Near riot on street car as Negro shoots two men.” Since there was no follow-up story in any of the city’s newspapers, its fair to assume the charges against Jackson were dropped.

In 1921 he was charged with carrying concealed weapons, but the charges were dropped.

Charity and Politics

Dodge School, North 11th and Dodge Streets, Omaha, Nebraska
This is the Dodge School, once located at North 11th and Dodge Streets. It became the city’s jail in the 1890s and was demolished around the turn of the century. It was also home to the police court while Jackson was a bondsman and one of the “men of influence” cited in the Omaha World-Herald.

Lending his name to political campaigns and charity organizations was a known tactic among criminal leaders since it suggested the support and endorsement of the underworld for particular candidates and causes.

Jackson was a political influencer among African Americans and throughout North Omaha. He never ran for elected office himself. Instead, Jackson was regularly cited as a person who supported particular Black political candidates in newspaper ads for political campaigns.

Close friends with Amos P. Scruggs, from the 1890s through the late 1910s Jackson was a main member of the Elks when Scruggs was the leader of the fraternal organization. Jackson attended the national Black Elks convention as a representative of North Omaha’s post. Throughout his life, Jackson was regularly thanked in the media for donating to Black-led and focused organizations in North Omaha, including the Omaha NAACP, the Roosevelt Post of the American Legion, and other efforts.

Death

On January 26, 1934, Ollie Jackson reportedly died of natural causes. His funeral was at St. Benedict’s Catholic Church, and he was buried at Forest Lawn Cemetery. The Elks performed the funeral rites.

In a report after his death, the Omaha Guide wrote, “We are wondering what will become of North Omaha now, since Tom Dennison, Ollie Jackson, Jack Broomfield, James Jewell, Missouri Jack, and Ralee Jackson, who stood in Class A in wide world elements… are now all over God’s Kindom where there is no hate, no enemies to punish, no friends to protect, no troubles of any kind, and when they must love everyone and everything.”

I guess we know what happened after that.

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