St. Paul man charged with drugging and sexually assaulting victim he met on dating app

A St. Paul man with an extensive criminal history spanning state lines has been charged with drugging and raping a man he met on a dating app and stealing his property.

Ramsey County authorities charged John Henry McCaster, 48, on Wednesday with first- and third-degree criminal sexual conduct in a rape reported Dec. 31. McCaster, who was arrested that night, has also been charged with vehicle and property theft.

Prosecutors say McCaster’s criminal history includes felony convictions in Minnesota and multiple drug crimes in Illinois, adding that they believe he poses a “very high” risk to public safety. He has been the subject of multiple police reports involving sexual assaults in the Twin Cities with and without the use of a gun, drugging victims, and theft of items from assault victims.

“When we announced a greater collaboration and implementation of our improvement plan on sexual assault investigations in 2019, we envisioned being able to uncover more cases like this where we would connect the dots with other victims across our region,” Ramsey County Attorney John Choi said in a statement. “We appreciate the dedication and collaboration between St. Paul police investigators and our assigned prosecutor to investigate and charge our most complex sexual assault cases.”

According to charging documents filed Friday:

At 11:47 p.m. on Dec. 31, St. Paul police were dispatched to a reported vehicle theft that happened earlier in the day on the 1500 block of Greenbrier Street. The victim told police that his cellphone, backpack, clothes and black Mercedes were missing. He also worried that the suspect may have sexually assaulted him.

The man told officers that he began talking to McCaster days before the incident on Grindr, an online dating app described as the largest social networking app for people who are lesbian, gay, bisexual, transgender and queer. The man agreed to meet McCaster, but he said they never made plans to be intimate that night. He told police he knew he would not have consensual sex with McCaster “as soon as he met [him],” adding that the 48-year-old spoke quickly and slurred his words as if he were under the influence.

Investigators have collected the blue liquid and sent it to the Minnesota Bureau of Criminal Apprehension for tests.

The victim “said he knew he had been raped,” the charging documents said, citing evidence he reported. “[He] downplayed the sexual assault to police at the time of the initial report because he was embarrassed and blaming himself ... [the victim] did go to urgent care after being advised to get a sexual assault exam but left after waiting two or three hours because he could not bear it anymore.”

McCaster was arrested that night for unlawful possession of a weapon and drugs. He had the victim’s personal belongings with him at the time. McCaster told investigators that he’s not a gun person and has not been on Grindr for around a decade, adding that he and the man had consensual sex the night of the assault. He also claimed that the victim gave him permission to use his Mercedes, which was purchased two days before the incident.

The victim denied consenting to sexual activity, or to giving McCaster permission to drive his car.

It’s unclear when McCaster’s next hearing will be scheduled, but prosecutors asked Judge Kellie Charles to set his bail at $150,000.

McCaster’s landlord said the 48-year-old has lived in the Greenbriar house since last March. He said McCaster did similar things to another man, adding that he believes McCaster is into an illegal depressant commonly known as a date rape drug. The landlord said he tried to evict him, but reported that McCaster brandished a chrome handgun and forced the landlord to put his belongings back in the apartment.

McCaster has at least seven felony convictions in Minnesota this past decade for crimes that include violating an order for protection and violating a no-contact order. Per a St. Paul police report last year, McCaster met someone from Grindr before pulling out a revolver and raping them. Another 2023 report alleges that McCaster met someone from Grindr for sex before stealing their wallet and personal items, and a 2007 report alleges that McCaster raped and beat a woman he knows.

A Minneapolis police report suggested that McCaster sexually assaulted a transgender person in 2020, and another report that year claims he drugged and sexually assaulted a man he met on Grindr. That victim woke up naked with several of their possessions stolen.

Charging documents also explained that McCaster has an “extensive” criminal history in Illinois that includes domestic battery, larceny and controlled substance crimes.

Police have asked any other victims to come forward and share information with authorities.