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On April 21, 1998 in Cherokee County, Georgia, Steiner threatened Georgia Department of Transportation employee Paul Kaspereen after Kaspereen informed him that an exit ramp leading off Interstate 575 was closed. He then twice hit Kaspereen with his Ford F-250 pickup truck (Kaspereen was not badly hurt). Steiner was subsequently arrested, and on March 17, 1999 he pled guilty to aggravated assault and making "terroristic threats" (felonies carrying a maximum sentence of 30 years imprisonment. Under Georgian first-offender rules, which stipulates that a first-time offender will be found not guilty if they do not violate the terms of their probation, Judge C. Michael Roach sentenced Steiner to 10 days in the Cherokee County jail. He also placed Steiner on a seven year probation order, ordered him to pay $25,000 USD in fines, restitution and legal fees and ordered him to perform 200 hours of community service.
Towards the end of his tenure in World Championship Wrestling, Steiner embarked upon a legitimate rivalry with wrestler Diamond Dallas Page after insulting Page's wife Kimberly during an interview. Kimberly Page had fallen afoul of Steiner after claiming that drug paraphernalia found backstage belonged to Tammy Lynn Sytch, an accusation that, despite Sytch's vehement denial, led to her being released from the promotion soon after. The acrimony between Steiner and Page eventually descended into violence, with the two men engaging in a locker room fight before being separated by other wrestlers. The incident was adapted into an on-screen feud between the two in which Page would repeatedly harass Steiner with the phrase "I'm still standing!", a reference to Steiner repeatedly boasting about having "ended the careers" of Goldberg, Sid Vicious, Sting, and Booker T.
In January 2001, Steiner was arrested after inadvertently assaulting Randall Mankins, an emergency medical technician employed by the Kernersville, North Carolina fire department. As part of an angle on an episode of WCW Monday Nitro, an EMT was sent to the ring to tend to Michael Modest and Christopher Daniels, who were selling leg injuries ostensibly inflicted by Steiner. As the EMT entered the ring, Steiner struck him twice, believing him to be a plant rather than a legitimate EMT. Steiner was arrested for assault the following morning as he tried to board a plane.
In December 2005, Steiner, along with Lex Luger and Buff Bagwell, was removed from a flight from Minneapolis, Minnesota to a destination in Canada following a disturbance onboard the plane. The three men were detained for several hours before Steiner and Bagwell were released and permitted to continue on their journey (Luger, however, was held without bail and later charged and jailed). Steiner would later invoke the incident in his in-ring interviews, describing himself as a violent criminal with little regard for the forces of law and order.