Whitefish Bay, Milwaukee police chases; plea deal reached

A Milwaukee man accused of leading Whitefish Bay and Milwaukee police on separate pursuits in less than an hour in February has reached a plea deal. 

Tonnie Gregory, 21, pleaded guilty on Monday, Aug. 28 to four of seven counts against him – including fleeing officers and second-degree recklessly endangering safety. The other three counts were dismissed, but read into the court record for the purposes of sentencing. 

Tonnie Gregory

Gregory is scheduled to be sentenced on Nov. 30. 

Case details

According to a criminal complaint, Gregory was out on bail for a separate case when Whitefish Bay police saw him driving 51 mph in a 25 mph zone near Santa Monica and Lancaster. He was driving a blue GMC SUV.

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At Santa Monica and Henry Clay, police tried to stop the SUV. The complaint states Gregory briefly stopped before reversing and pulling forward in an attempt to maneuver past a police squad. He then sped off in reverse until there was an opening in the median on Santa Monica.

Dashcam video of Whitefish Bay police chase, Tonnie Gregory charged

Police again tried stopping the SUV, but prosecutors said Gregory reversed and pulled forward again, tried to get past the squad, reversed in the wrong direction at 40 mph, nearly struck parked cars and caused other drivers to take evasive action.  

The complaint states, after Gregory reversed over a median and hit a squad, officers positioned their vehicles for a high-risk traffic stop. 

An officer was able to grab onto the steering wheel through the open driver's side window while other officers pulled a passenger from the SUV. Prosecutors said Gregory pulled forward, and an officer – fearing he would be hit – drew his service weapon. 

Dashcam video of Whitefish Bay police chase, Tonnie Gregory charged

"If you drive, you’re going to get shot! Turn it off!" an officer can be heard saying. "Turn it off! You’re going to get shot! You’re going to get shot."

Gregory then sped off, per the complaint. The Whitefish Bay pursuit was terminated when officers lost sight of the SUV. 

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About 45 minutes later, Milwaukee police spotted the SUV near 71st and Hampton. Prosecutors say Gregory again sped away from officers. 

Dashcam video of Whitefish Bay police chase, Tonnie Gregory charged

A Milwaukee police pursuit ended when Gregory crashed into a pole in an alley between 77th and 76th Streets. The complaint states his vehicle rolled over. 

Two other squads also struck poles as the pursuit, which stretched 2.1 miles, came to an end. Prosecutors said it reached speeds of 80 mph – more than double the speed limit in the area.

After the crash, the complaint states Gregory took off running, scrambling through yards in the neighborhood near 77th and Kathryn, where he was eventually taken into custody. Prosecutors said he had THC and cocaine on him.