On August 23, 1995, Donnah Winger was driven from St. Louis International Airport to her home in Springfield by shuttle driver Roger Harrington. The Wingers complained to Harrington's employer, saying that Harrington gave Donnah a "hard time" during the ride by talking about getting high and having orgies. Some days later, Mark Winger called 911, saying that he had shot Harrington to death after Harrington attacked Donnah with a hammer. The police initially believed that Harrington had broken into the Wingers' home and attacked Donnah in retaliation for their complaint, but became suspicious of Winger because he continued to ask about the case even after it had been initially closed. "He kept coming in. I kept feeling like he was trying to find out if we were checking into anything," said a detective. Winger's remarriage to his small daughter's new nanny, hired five months after Donnah died, increased suspicion. Winger had three children with his new wife. The police eventually concluded that the positions of Donnah's and Harrington's bodies were inconsistent with Winger's account of a struggle with Harrington. They also found evidence in Harrington's car that Winger had invited Harrington to the Winger home. The new theory was that Donnah's upsetting ride with Harrington inspired Winger to plan to kill Donnah with the hammer and then shoot Harrington, using the story of an attack by Harrington as a cover. He was arraigned in 2001. Evidence introduced at trial included recorded conversations between Winger and Harrington arranging a meeting on the day of the murders. Testimony from paramedics that they found Donnah face down contradicted Winger's statement that he had held his wife before they arrived. A close friend of Donnah's testified that she had been having an affair with Winger at the time of the murder, that Winger had tried to involve her in his plot, and that Winger had told her, "It would be better if she died." In May 2002, a jury convicted Winger of the first-degree murders of Donnah and Harrington, and he was sentenced to life in prison without parole.
In 2006, Winger was indicted for asking a fellow prison inmate to arrange the murders of DeAnn Schultz, his girlfriend at the time of the murders; and a childhood friend, Jeffrey Gelman, whom Winger resented for refusing to post his $1million bail. Winger initially wanted Gelman kidnapped for ransom, but also wanted Gelman and Schultz killed. In June 2007, Winger was convicted of solicitation of murder, and a 35-year sentence was added to his existing life-without-parole sentence. Winger's second wife never remarried and raised all the Winger children on her own.