Historic Omaha

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Above: “Cowboy Jim” Dahlman, flamboyant
mayor and mouthpiece for “Boss” Tom
Dennison, served for all but three years
from 1906 until his death in 1930.
COURTESY OF THE DOUGLAS COUNTY HISTORICAL
SOCIETY COLLECTIONS.
Right: Heavyweight boxing champion Jack
Dempsey is greeted at the railroad station
by long-time Omaha Mayor James C.
Dahlman in 1923.
COURTESY OF THE DOUGLAS COUNTY HISTORICAL
SOCIETY COLLECTIONS.
HISTORIC OMAHA
46
of Assignation” highly lucrative, averaging
$17.5 million annually in collective profits
between 1905 and 1911.
During most of this time, Omaha had as its
mayor James “Cowboy Jim” Dahlman,
Omaha’s mayor for all but three years from
1906 until his death in office in 1930.
Dahlman was a hands-on mayor, rarely
delegating even the smallest decisions to his
staff. He would personally speak to a
constituent with a problem or visit a citizen in
jail. Frequently, Dahlman pardoned an inmate
convicted of drunkenness or some other
“trivial” offense. He once commented, “If it
was the man alone who paid the penalty for
the offense, I would let him stay in jail. I
cannot see a mother and children suffer
because the husband and father drank a little
too much.”
His popularity with the citizens of his
community was part of the secret to Dahlman’s
longevity as mayor, a longevity that earned
him the title, “The Perpetual Mayor of
Omaha.” The major factor in his long run as
mayor was the support he enjoyed from
Omaha’s political “boss,” Tom Dennison.
Dennison, also known as “The Old Man” came
to Omaha in 1892 at age thirty-four. This
nickname changed to “the Old Grey Wolf” in
1933, during Dennison’s last campaign, when
his opponents sang “the old grey wolf he ain’t
what he used to be”, but to his followers, he
was always The Old Man. As George Leighton
of Harper’s Bazaar tells it, Dennison showed
up with $75,000, which he deposited at a
local bank, telling the banker that $50,000
was for the banker to use as he chose.
Within a few years of his arrival in Omaha,
Dennison had launched an enormously
successful gambling business and made
connections with nearly all of the City’s
powerful elite. Although gambling wasn’t
actually legal, it was a common sight to see
Dennison being escorted throughout the town
by members of Omaha’s police force. The
gambling houses, which suffered from the
most frequent and destructive police raids,
always seemed to be those owned by
Dennison’s fiercest competitors, while his own
establishments escaped unscathed.
Keeping his business interests alive was
Dennison’s greatest concern, and he showed a