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Ritter was the subject of two law enforcement sting operations in 2001. He was charged in June 2001 with trying to set up a meeting with an undercover police officer posing as a 16-year-old girl. He was charged with a misdemeanor crime of "attempted endangerment of the welfare of a child". The charge was dismissed and the record was sealed after he completed six months of pre-trial probation.

Ritter was arrested again in November 2009 over communications with a police decoy he met on an Internet chat site. Police said that he exposed himself, via a web camera, after the officer repeatedly identified himself as a 15-year-old girl.

The next month, Ritter waived his right to a preliminary hearing and was released on $25,000 unsecured bail. Charges included "unlawful contact with a minor, criminal use of a communications facility, corruption of minors, indecent exposure, possessing instruments of crime, criminal attempt and criminal solicitation". Ritter rejected a plea bargain and was found guilty of all but the criminal attempt count in a courtroom in Monroe County, Pennsylvania, on April 14, 2011.

In October 2011, Ritter received a sentence of one and a half to five and a half years in prison. He was sent to Laurel Highlands state prison in Somerset County, Pennsylvania, in March 2012 and paroled in September 2014. Car park masturbation

In the early 2000s, Ritter and his wife Marina joined Delmar’s volunteer Fire Department. Ritter became one of its most active members, and was eventually selected as an assistant chief. According to court testimony, by 2004 when Ritter stopped attending therapy, he had made an almost daily habit of trying to meet women from chat rooms, in cars or out-of-the-way places, so they could watch him masturbate. Ritter has blamed this behavior on his ongoing depression. In 2009, when Ritter's sexual offenses with a minor became public, he lost the only regular job he had had in recent years, writing analyses on world events for a private energy firm, and was reported to be heavily in debt. Also at this time, Ritter was also removed from active duties in the Delmar Fire department, something he described as “one of the most profound disappointments I have experienced.”

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In April 2022, shortly after the start of the Russia's invasion of Ukraine, Ritter tweeted that the National Police of Ukraine was responsible for the Bucha massacre and that U.S. President Joe Biden was a "war criminal" for "seeking to shift blame for the Bucha murders" to Russia. Ritter had not apparently commented previously on Ukraine, or Russia.[48] Human Rights Watch found evidence linking the killings to the Russian military. Ritter was suspended from Twitter for violating its rule on "harassment and abuse" after this, but his account was reinstated the next day. Ritter's strongly pro-Russian position quickly attracted negative global attention.

In 2022, Ritter became a contributor to Russian government-owned media outlets RT and Sputnik. He compared Ukraine to a "rabid dog" that needed to be shot. He compared the treatment of Russians under Ukraine law to Nazi Germany's treatment of Jews. In October 2022, he posted a provocative tweet about Bucha, stating "Bucha was a war crime, Ukraine did it", to test the reaction of Twitter.[56] DisInfoChronicle (the website of NGO Detector Media that claims to refute Russian disinformation) wrote that Ritter was being used by Russia to "promote narratives needed by the Kremlin".

Really, fuck this dude.