A History of Early 20th Century Crime Bosses in North Omaha

Billy Crutchfield and Harry Buford North Omaha Nebraska

In a time of mobland gangsters, illegal booze, dirty gambling halls and open prostitution, several African Americans rose high enough in Omaha’s criminal underworld to become the crime lords of North Omaha. They included Ollie Jackson (1865-1934), Jack Broomfield (1865–1927), Billy Crutchfield (1875–1917), and Harry Buford (1890–1951).

The mayor during these years, “Cowboy” Jim Dahlman (1856–1930), openly flaunted his connections with the city’s criminal boss, Tom Dennison (1858–1934). Dennison bought off judges, politicians, high society leaders, and others throughout Omaha, and made a point of having co-called Black lieutenants around the city on his payroll to make sure he controlled all corners.

Reading the history, it seems like a lot of people were involved in Omaha’s criminal underworld back in the day, including politicians, judges, police leaders and policemen, and a lot of other people. In 1906, the Omaha World-Herald wrote,

“The policy of our police department is bearing legitimate fruit. A gang of desperadoes has been encouraged to make Omaha it’s haven of refuge and it has educated a lot of young men in the ways of crime. The doctrine that ‘when permitted to live in Omaha they commit all their misdeeds outside the city’ is almost as false as it is immoral.”

-from the Omaha World-Herald (1906)

Here are the stories of those men.

Tom Dennison

Tom Dennison North Omaha Nebraska
Omaha’s most hyped political boss, Tom Dennison, lived at 1507 Yates St in a two-story wood house from 1902-1919. He also lived on Florence Boulevard after that, but only for a few years.

None of the following stories are complete without digging into the Old Grey Wolf himself. You see, Tom Dennison was a North Omaha boy. His father moved the family from rural Iowa to Omaha when he was a kid, and after he’d traveled the West to sow his wild oats, Dennison came back to the city to make his name.

Omaha’s most hyped crime boss lived at 1507 Yates Street in a two-story wood house from 1902-1919. The house sat on the edge of a cliff, and surely had a tunnel that routed out to the Belt Line Railway and the road below. During that time, he rigged elections, managed the city’s entire crime syndicate, and started Omaha’s worst riot ever.

When his fortunes improved, Tom Dennison moved to a swank North Omaha house at 6141 Florence Boulevard. This house gets a lot of press for Dennison’s time spent there, but in reality he only lived there for three years. Built in 1915, Dennison and his wife Ada moved in 1919. However, in 1922 she had a stroke and passed away suddenly. Dennison moved out soon after.

Dennison moved on after that, eventually getting to a swanky address in northwest Omaha. However, his most deviant days were spent in North O. And he set up everyone else who follows, too.

Ollie W. Jackson

Ollie Jackson (1865-1934), North Omaha, Nebraska
This was Ollie Jackson (1865-1934), an African American criminal figure, in 1898 while he was sitting in the Omaha police court while working as a bondsman.

Born in 1865, Ollie William Jackson was an old-time Old West criminal, involved in sophisticated messes and mastering simple destruction. A reputed burglar, stickup man, robber and strongman, Jackson was also a political muscle who steered votes; a charity guru who helped set up operations; and an early lieutenant of crime boss Tom Dennison who helped secure the Black community’s support for a variety of enterprises, both criminal and otherwise.

My research shows no fewer than 20 arrests by the Omaha Police Department; however, it also shows how Jackson was regarded as one of the “men of influence,” as Jackson was a bondsman and seen as a generally significant individual.

When he died in 1934, Jackson was lavished with a large funeral by the Black Elks in North Omaha and he was buried at Forest Lawn.

Vic Walker

Victor Walker (1864-c1924)
This might be Omaha’s Victor Walker (1864-c1924), pictured in 1914 when he was living in Denver.

Born in 1864, Victor B. Walker was a soldier, political activist, lawyer, civil rights activist, police officer, saloon owner, journalist, and gangster in Omaha. Before coming to Omaha, he served as a Buffalo soldier, and when he first got to the city, he worked as a police officer.

Walker moved to Denver after that. There, he ran a nightclub, was appointed deputy sheriff, and briefly ran a weekly newspaper. He was heavily involved in criminal activity there, and was known as the “King of the colored underworld” in Denver. Last arrested in Denver in 1924, the date of Walker’s death is unknown. He is buried in the historic Riverside Cemetery in Denver.

Jack Broomfield

The Broomfield Rowhouse at 2502 Lake Street was designed by Clarence Wigington and built in 1913.
The Broomfield Rowhouse at 2502 Lake Street was designed by Clarence Wigington and built in 1913. It was owned by Jack Broomfeld, Billy’s partner. Crutchfield owned one identical to it just to the west.

After Walker was ridden out on a rail, Jack Broomfield stepped into the position of the political leader of Omaha’s African-Americans.

Born in 1865, Jack Broomfield was once a Pullman porter. His career with the railroad ended he was in a train wreck that resulted in the loss of his leg, but left him with some money when he arrived in Omaha in 1887.

Around 1904, Omaha’s boss, Tom Dennison, gave Broomfield co-ownership of the Midway. In a report on the city in the early 1910s, suffragette leader Elizabeth Cady Stanton called the Midway the “most notorious dive in Omaha.”

We only have to look at the 1912 raid on Broomfield’s Midway to see how corrupt Omaha was. Storming the joint in full force, Broomfield and several of his customers were cited and ordered to show up for court. Broomfield’s four trials were held in the Douglas County Court, all of them ending in hung juries. At the last one, when a juror didn’t show up, a substitute was chosen from the crowd. Coincidentally, he became the only member to vote to acquit Broomfield. After a grand jury ordered the case moved to district court, two more trials ended in deadlock, and the case was dismissed.

By 1916, the Omaha World-Herald was barking again and calling Broomfield’s Midway, “the … most vicious of gambling and liquor joints to be found in this or any other city.”

Omaha’s African American community wasn’t especially proud or congratulatory of Broomfield or his actions. During his more than two decade reign over the Near North Side, newspapers such as The Monitor and The Enterprise complained that Broomfield was more interested in promoting his own interests than promoting the interests of his community. Broomfield was slipping: He said he would wrangle votes to keep Blacks in office, but allowed many positions formerly held by African Americans to be taken by whites.

In early 1919, a Dallas newspaper reported that Broomfield was an advisor to an all-African American owned oil company based in Kansas City.

It was also under his watch that the lynching of Will Brown occurred. While it is difficult to say whether any African-American leader could have prevented such mob terrorism, its not impossible to see Broomfield’s role. He apparently did nothing to prevent the subsequent redlining of the Near North Side and other forms of segregation throughout the city, too.

Broomfield is remembered today because he contracted local African-American architect Clarence W. Wigington to build the Broomfield Rowhouse at 2502-2504 Lake Street in 1913.

Broomfield died on September 7, 1927. Upon his death in Lincoln, the local paper there said he was, “supreme dictator of negro politics in Omaha.”

Dennison was a pallbearer at Broomfield’s funeral, where he said Broomfield was,

“one of the old school of political workers and he could always be depended upon to take care of the colored vote and he never failed… [Jack] was true blue and always loyal.”

Billy Crutchfield

Billy Crutchfield North Omaha Nebraska
North Omaha crime lord Billy Crutchfield (1875-1917) circa 1910.

Born on May 8, 1875, Billy Crutchfield was a significant leader in Omaha’s crime world.

An Omaha Bee article from 1898 shows that William Crutchfield was involved in crime for a long time. That year, his house was bombarded with gunfire when it was being raided by police. Often called Billy, Crutchfield was Jack Broomfield’s partner for a long time. In 1903, when Tom Dennison positioned Broomfield as the owner of The Midway saloon, he made Crutchfield part-owner. When Broomfield commissioned Wigington to design his rowhouse, Crutchfield built an identical one next door.

Crutchfield co-owned the Midway with Crutchfield until 1914, when he opened his own establishment in the Sporting District. The Midway was known nationwide and apparently catered mostly to African-Americans. They served alcohol and gambling of all sorts, including poker, blackjack and craps, as well as faro, roulette, dice and cards. At one point there was a sign in the Midway that said, “If you have a family that needs your money, don’t gamble here.”

A visitor to the city in 1915 said Crutchfield was a big time politician. He successfully invested in real estate throughout his life, and when he died he left a $10,000 dollar estate, including giving his family home at 2517 Patrick Avenue to his wife, who was a white woman.

The Crutchfield Rowhouse, which was immediately west of Broomfield’s at 2506-2508 Lake Street, was destroyed in a fire that happened in 1986.

Crutchfield died on November 15, 1917, and was buried in Forest Lawn. His family home still stands today.

Harry Buford

Harry Buford, North Omaha, Nebraska
This is a feature on Harry Buford from the November 6, 1915 Monitor newspaper.

Harry Buford was born in 1890, and was a much more highly regarded leader in North Omaha than his predecessors – but no less wound up in the shady crime world. He grew up in North Omaha and was a determined man, which led to him becoming a policeman.

After starting with the Omaha Police Department, Buford became an acknowledged lieutenant of Tom Dennison for more than 20 years.

While working as a police chauffeur, he routinely carted around Dennison, who deliberately positioned him to become the crime boss of the Near North Side. While on duty in 1913, Buford hit two children playing in a street along South 10th Street. He faced no charges. Referred to as one of four “ward heelers” in the city, Buford was used to control over the Black neighborhood in North Omaha.

By 1930 Buford had worked his way up to become a police lieutenant, and by 1940 he had become a detective for the city police department. He retired from the Omaha Police Department as a sergeant detective.

Harry Buford House, 1804 North 30th Street, North Omaha, Nebraska
This is the Harry Buford House at 1804 North 30th Street in North Omaha. Its remarkable for breaking the redline for African Americans in Omaha. Today its listed on the National Register of Historic Places.

Harry Buford became so successful in Omaha that he broke the race line. In 1929, the location of his family’s home on the west side of North 30th Street indicated the status of the Buford family because it was outside the redlined Near North Side neighborhood. It was designated an Omaha landmark in 1983.

Buford died in 1951.

Remembering Criminals

As several of these mens’ stories show, the lives of historic criminals weren’t always straight lines from birth to crime to death. Instead, they are complicated people who lived in complicated ways. Vic Walker was a policeman before he became a crook; Buford worked for the police while he was a crook, and was lauded by the Black press for being a success. Walker even fought for civil rights in court!

However, Broomfield and Crutchfield come off as criminals who started badly, and ended that way too. Getting eulogized by Tom Dennison might’ve been an honor at the time, but today we know it was a signal that these were mob men.

This article isn’t meant to be a tribute to these men. Instead, it’s a reminder that the forces of crime and capitalism have been tugging at the heart of North O for more than a century. Let’s not forget the lessons we need to learn.

You Might Like…

Elsewhere online

  • Victor B. Walker” on Wikipedia
  • Jack Broomfield” on Wikipedia
  • “Harry Buford, Police Chauffeur Making Good,” The Monitor. November 6, 1915 (see below).
  • John Kyle Davis, “The Gray Wolf: Tom Dennison of Omaha,” Nebraska History 58 (1977): 25-52.
  • Special thanks to Wikipedia editor User:Smmurphy for their volunteer labor on behalf of North Omaha.


Monarch Billiard Parlors, 111 South 14th Street, Omaha, Nebraska
Jack Broomfield owned the Monarch Billiard Parlors in downtown Omaha.


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