Time Machine: Omaha crime boss

Thomas Dennison, who would grow up to be an Omaha political and crime boss, was born on a farm in Delaware County in 1859.

His first job was putting in wastepaper boxes in Des Moines in the early 1870s. He worked on Iowa farms from 1873 to 1879, when he headed to Colorado to work in the silver mines. He then became a professional gambler in Leadville, Colo., later buying into the Arcade gambling house in Denver.

In 1890, Dennison moved to Lincoln, Neb., and then on to Omaha within two years.

Dennison became a protégé of Omaha Bee Editor Edward Rosewater, who ran the Republican political organization in the city. When Rosewater became more interested in state and national affairs, Omaha became Dennison’s domain.

Under Dennison, the organization transitioned into criminal enterprises, operating out of the city’s Third Ward, where gambling, drinking and prostitution flourished.

Iowa train robbery

The defining episode in Dennison’s career — and the one that almost sent him to prison — was a daring train robbery on Nov. 4, 1892, in western Iowa.

As the Sioux City and Pacific Railroad train out of Omaha drew near California Junction, a settlement in Harrison County, Iowa, just across the Missouri River from Nebraska, a ruthless young robber jumped off the train, rolled down an embankment and disappeared with $15,000 in diamonds taken by brute force from traveling salesman W.G. Pollock of New York. The diamonds would be worth more than a half-million dollars today.

William A. Pinkerton, from the famous private detective agency, interviewed witnesses on the train, who identified the robber as James Burke, alias Kid McCoy, alias Frank Shercliff. Shercliff was arrested, convicted and sentenced to 17 years in the penitentiary at Fort Madison.

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Shercliff had the reputation of being ready to carry out any crime requested of him and was therefore valuable to Dennison.

Political pressure was applied to Iowa Gov. Frank Jackson to have Shercliff pardoned, to no avail. Rich gamblers in Denver and Omaha tried again to get Shercliff pardoned when Iowa Gov. Francis Marion Drake (for whom the university is named) took office, again without success.

Shercliff finally was released on parole by Iowa Gov. Leslie M. Shaw on Nov. 28, 1900. Shaw was under the impression that the presiding judge, A. Van Wagenen of Sioux City, approved. He didn’t.

The only letters in favor of the parole came from John Baldwin of Council Bluffs and Judge N.M. Hubbard of Cedar Rapids, who said he was returning a favor for Congressman David Mercer of Omaha, who “had been very useful to him in getting a bill through Washington,” The Gazette reported.

Dennison charged

Shercliff, who by then identified as Sherman Morris, son of Marshall County stockbroker W.H. Morris, returned to crime almost immediately after being released and was caught attempting another diamond robbery. He was returned to prison to complete his original sentence.

He asked Dennison for help, but Dennison wasn’t interested this time. Shercliff, in turn, decided to provide state’s evidence incriminating Dennison, saying Dennison had received the stolen diamonds in the 1892 train heist and in a 1902 diamond robbery in Clinton.

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In April 1904, a Harrison County grand jury indicted Dennison on charges of receiving the stolen diamonds from the Pollock robbery in 1892. Dennison was accused of trying to defeat the Harrison County attorney in the 1904 election. Shercliff, in fear of his life, was put under police protection in Harrison County.

The Des Moines Capital newspaper interviewed Dennison, who admitted putting up money to secure Shercliff’s parole in 1900. “Of course, political influence entered into the case,” he stated. A document also surfaced that showed Dennison had hired H.G. McMiller, an attorney and editor of the Cedar Rapids Republican, to serve as Shercliff’s lawyer.

But at Dennison’s trial in June 1905 — moved to Red Oak on a change of venue — Dennison denied knowing Shercliff other than as a gambler in Salt Lake City. The jury acquitted Dennison on any role in the diamond robbery.

Three years later, in September 1908, Dennison testified against Shercliff, who had been charged with second-degree murder in the killing of a Leadville, Colo., saloon keeper in 1893. Shercliff was convicted and sent to prison again.

Still in power

After his acquittal, Dennison resumed control of his Omaha organization, which was credited with electing “Cowboy Jim” Dahlman mayor of Omaha eight times.

Documents showed he’d paid to have Blacks transported from Council Bluffs to Omaha to pad the vote in a senatorial election. He also was suspected of ordering the dynamiting of an opponent’s home.

In 1918, Omaha voters had had enough and elected Edward Parsons Smith as mayor on a reform ticket. Dennison is thought to have incited the Omaha Race Riot of 1919 in retribution.

The new mayor began targeting Dennison’s crime operations, but for three years his efforts were undermined by violence. Dennison and “his” candidate once again took control of the city in 1921.

By 1932, during Prohibition, Dennison was 73 and in federal court in Omaha as a defendant in a liquor conspiracy trial. Witnesses testified he’d visited gangster Al Capone in Chicago to learn how to modify Omaha’s liquor syndicate to mirror Capone’s. The federal jury deadlocked, and Judge J.W. Woodrough declared a mistrial.

With his health declining, Dennison retired in 1933, ending his 30-year reign in Omaha, and the Independent Voters’ League came into power.

On Feb. 14, 1934, Dennison, who was never convicted of a crime, died in San Diego, Calif., from injuries sustained in a Jan. 27 car accident. His body was returned to Omaha for burial, with hundreds attending his funeral.

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