Gambling had been shut down in Seattle in April 1899, but in September it had been reopened with John Considine as leader of the gambling trust. While gambling was still illegal, it was permitted under certain conditions. The leading gamblers laid down the rules during a September meeting in the office of Police Chief Reed, and these rules were in place two months later when partners Earp and Urquhart opened their doors:

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No. 1 No minors allowed to participate.
No. 2 No drunks admitted.
No. 3 Must place door-tenders.
No. 4 No crap or blackjack games.
No. 5 Police to notify when fines are due.
No. 6 Doors to close at 3 a.m. except on
Saturday night. When business
must close at midnight.
No. 7 No entrance to gambling games
from any saloon.

The city was reaping a bountiful harvest in fines, and the gambling houses employed about 1,000 men. Gambling was big business in Seattle, and the established proprietors had a promising future. In October 1899, the Star interviewed a gentleman identified only as a "well known sporting man" who claimed to be an insider in the gambling fraternity: "Several days ago I overheard a conversation between Dave Argyle, one of the proprietors of the White House, in which he stated that the Seattle gamblers 'cut up' $50,000 in their last monthly settlement, and if permitted to run until April, would clear between $350,000 and $300,000 above all expenses including 'hush money.'"

The Seattle Star sent a reporter around to the gambling houses on December 12, 1899, and reported in next day's edition: "Earp and Urquhart's new house, the Union Club…is having a large patronage. When it was first opened, about two weeks ago, five games were run. Last night the management placed several new games on the floor." The newspaper reported the following fines from the police records:

The Standard, fourteen games $400
White House, six games $200
Horseshoe, eight games $250
Clancy House, five games $175
Union Club, five games $175

In January 1900, Seattle became the scene of what the Daily Times described as a "Gambler's War." Clancy House—not part of the original combine of the White House, the Standard and the Horseshoe—was shut down because John Clancy was running lotteries, one of the prohibited forms of gambling. Clancy had a beef: The other houses were running prohibited types of games, and therefore he should be allowed to run his lotteries. In reality, all gambling was illegal, but enforcement was selective. Determined to not let others have their cake, Clancy swore out complaints against the Standard and the Horseshoe. Indeed, those two houses were both shut down, according to the January 28 Seattle Post Intelligencer. It was expected that Earp and Urquhart's Union Club would be next if the proprietors did not close of their own accord. The Post Intelligencer reported on February 1, 1900, that the Standard and Horseshoe had reopened. The same article indicated that evidence was being gathered to swear out warrants against Earp and Urquhart as well as the California Club run by David Argyle. No charges were filed against Earp and Urquhart in that particular round.

Court records show that city officials charged Urquhart, along with H.B. Kennedy, proprietor of the Horseshoe Club, with conducting gambling games on January 10, 1900, February 13, 1900, and March 12, 1900. This all occurred during the time when Wyatt Earp was Urquhart's partner in the Union Club. For whatever reason, Urquhart was not charged in his business with Wyatt.

Apparently, Wyatt made a big enough splash in the community to be referenced in a Seattle Daily Times story of December 4, 1899, about the welterweight championship bout between Peter Jackson and Arthur Walker. The betting was heavy and many well-known sporting men were expected to be in attendance. Wyatt Earp was given top billing, followed by John Considine. Wyatt had not only waltzed into Seattle and opened a gambling house, apparently against Considine's wishes, now he had seemingly bypassed Considine in local celebrity status.

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