The former chief executive of online bookmaker Betonsports has pleaded not guilty to racketeering and other charges in the US.
A warrant has been issued for the arrest of Betonsports' founder
David Carruthers was arrested as part of a US move to tackle internet gaming.
Mr Carruthers, 48, was ordered to be held while a bail arrangement, based on a $1m (£539,000) bond, was worked out.
Meanwhile a court order in St Louis, Missouri, has been made, extending till 14 August the block on the firm from taking US bets.
Mr Carruthers was sacked by Betonsports after his arrest by US authorities while passing through a Texas airport.
Bail terms being negotiated by the prosecution and defence would require him to post a $1m bail bond, remain in the St Louis area pending trial, and have his movements monitored with a global positioning system device.
He is one of 11 people and four firms charged in a 22-count indictment alleging racketeering, fraud, tax evasion and conspiracy.
Others pleading not guilty were Neil Kaplan, Lori Kaplan-Multz, Tim Brown, William H Lenis, William L Lenis, Manny Lenis and Monica Lenis. All were freed on bail.
A warrant has been issued for the arrest of Betonsports founder Gary Stephen Kaplan, 47, who is charged with 20 offences including tax evasion and conspiracy.
Betonsports, whose biggest market is in the US, is currently complying with the court order by not taking bets from gamblers in the US.
The charges allege that the firm failed to pay US excise taxes on more than $3.3bn in bets taken from US gamblers.
The authorities are seeking forfeiture of $4.5bn, removal of access to Betonsports sites in the US and the return of money held for US account holders.
Betonsports was not represented in court.