Man guilty of carjacking now faces chase charges in Ozaukee

Now it’s Ozaukee County’s turn to prosecute a 25-year-old man who fled the scene of a Sheboygan Falls shooting in an SUV he carjacked from a woman at gunpoint on charges he led officers on a high-speed chase in the stolen vehicle at speeds of about 125 mph on a busy I-43 in June 2025.

Hennessy M. Drain of Milwaukee made his initial appearance in Ozaukee County Circuit Court on July 14. Judge Sandy Williams set bail for Drain, who is serving a prison sentence for crimes he committed in Sheboygan County, at a $5,000 signature bond.

Drain was charged on July 7, 2025, in Ozaukee County with fleeing an officer and four counts of second-degree recklessly endangering safety, all felonies, but the case was essentially paused while he was prosecuted in Sheboygan County on related charges.

On April 23, a Sheboygan County jury found Drain guilty of all five felonies he was charged with — first-degree recklessly endangering safety, carjacking while armed, two counts of intentionally pointing a gun at a person and being a felon in possession of a firearm.

He was sentenced on May 15 to 20 years in prison followed by 24 years of extended supervision. Wisconsin Department of Corrections records indicate he is currently serving that sentence at Dodge Correctional Institution in Waupun.

Now that the Sheboygan County case against Drain is closed, the one in Ozaukee County can proceed.

According to the criminal complaint, Drain fled south on I-43, racing through Ozaukee County and forcing multiple drivers to take evasive action to avoid him in late-afternoon rush hour traffic on Wednesday, June 11, 2025, stopping only after he crashed into another vehicle in Milwaukee County.

He was arrested after trying to run away from officers.

The chase began at 4:52 p.m. after Ozaukee County sheriff’s deputy Steven Henning, who had received a report that the driver of a stolen Jeep Cherokee linked to the Sheboygan Falls shooting earlier that day was driving south on I-43, spotted the vehicle near the Highway 33 exit in Saukville.

Henning activated his vehicle’s emergency lights, but the driver of the Jeep, later identified as Drain, sped away from the deputy.

As Drain sped south at between 100 and 115 mph, Henning saw a box truck and SUV take evasive action to avoid him, the complaint states.

Henning asked the Grafton Police Department to deploy spike strips at Highway 60, but that effort to stop Drain was unsuccessful because of heavy traffic and his speed.

At one point during the chase, Drain lost control of his vehicle and struck a guardrail, nearly hitting a Chevrolet Suburban, but continued south, according to the complaint.

Drain exited the freeway at Highland Road in Mequon, struck a stop sign at the top of the ramp, then re-entered the freeway.

As he approached a construction zone, where there were concrete barriers on both sides of the freeway and traffic was becoming congested, he increased his speeds to 120 to 125 mph and sped into Milwaukee County.

Near Brown Deer Road, Drain began driving on the shoulder of the freeway, causing multiple vehicles to move over to avoid being hit, the complaint states.

Drain eventually hit spike strips deployed by state troopers near Good Hope Road, lost control of the SUV and crashed into another vehicle.

He ran from his vehicle, then fell down but got up and continued running until eventually surrendering.

The chase lasted 12 minutes and covered 19 miles.

Earlier that day, officers responding to a 911 call found a man in the kitchen of his Sheboygan Falls home shot in the back and unable to move his legs.

“I’m shot. I’m shot in the back. I’m paralyzed,” the man told a dispatcher, according to a partial transcript of his 911 call contained in the criminal complaint filed in Sheboygan County Circuit Court. “Two people were shooting at each other and I got caught in the crossfire and shot in the back.”

The man said Drain, who is his godson, and a woman he was with got into an argument, which precipitated a confrontation between Drain and the man’s other godson, who was also staying at his house and told Drain he had outstayed his welcome and should leave, the complaint states.

The man said Drain pulled a handgun from his waistband, which is when he turned toward the other godson and told him to leave, the complaint states. That is when Drain shot him in the back twice, the man said.

The other godson was also shot.

A woman who had driven her boyfriend to the house and was waiting in her Jeep Cherokee with another person outside the home said shortly after she heard what sounded like gunshots, Drain jumped in the passenger seat, put a gun to her head and ordered her to drive him to Milwaukee, according to the complaint.

The woman and the other person in the vehicle jumped out and Drain sped off in the Jeep, the complaint states.

In Ozaukee County, Drain is charged as a repeat offender because in 2020 he was convicted of battery by a prisoner in Milwaukee County.