High-speed pursuit of attempted murder out of Osceola County ends in crash, arrest in Winter Park | FOX 35 Orlando
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High-speed pursuit of attempted murder out of Osceola County ends in crash, arrest in Winter Park

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Updated  March 26, 2025 11:06pm EDT
Orange County
FOX 35 Orlando

High-speed pursuit of attempted murder

Osceola County sheriff’s deputies were in pursuit of a suspect, later identified as Jordan Bailey, wanted for attempted murder. The pursuit crossed into Orange County, where law enforcement agencies from both counties assisted in apprehending him.

The Brief

    • Osceola County deputies pursued Jordan Bailey, wanted for attempted murder, into Orange County, where a crash occurred during the chase.
    • Bailey, a convicted felon, was involved in a shooting on March 13 and was apprehended with the help of multiple law enforcement agencies.
    • Witnesses described the intense scene, with quick police responses and helicopters overhead.

WINTER PARK, Fla. - Osceola County sheriff's deputies said they pursued a homicide suspect into Orange County late Wednesday afternoon, ending in a crash in Winter Park.

Cross-county pursuit ends in crash

What we know:

Osceola County sheriff's deputies were pursuing a suspect in an attempted murder across the county line and into Orange County late Wednesday afternoon, where deputies from the Orange County Sheriff’s Office and other law enforcement agencies assisted in apprehending the man.  

The arrest followed a crash on Clay Street, near W. Fairbanks Ave. in Winter Park. A maroon truck, appearing to have front-end damage, was involved in a collision with an Osceola County deputy's vehicle, which also sustained damage. 

Booking photo of Jordan Bailey provided by Orange County jail

Osceola County sheriff’s deputies were in pursuit of Jordan Bailey, identified as the driver of the truck. He was taken to a hospital in an ambulance.

The backstory:

Jordan Bailey is connected to a March 13 shooting on Pershing Street, where he is accused of attempted murder. He is also a convicted felon and not allowed to possess a firearm. The pursuit involved multiple law enforcement agencies, including the U.S. Marshals and Florida Highway Patrol, all working together to capture him.

What we don't know:

The exact details leading to the crash are unclear, but it appears Bailey collided with the deputy’s vehicle during the pursuit. It's also unclear how the crash occurred in terms of speed or what caused the collision.

What they're saying:

Kevin Skaff, a witness to the crash, described the scene.

"I smelled like burnt rubber, and he told me that some dude got T-boned out here," he explained. "The police officers that came — they were here in like three seconds. It was crazy. I’ve never seen that fast of a response for anything, but there were also two helicopters in the sky too. It was a pretty narley scene."

"I see a red truck just zooming down the street, and I’m like, 'Oh, okay what’s going on?' and then one of the cop SUV cars was in hot pursuit," said another witness, Odelle Marshall.

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The Source: This story was written based on information shared by the Orange County Sheriff's Office. 

Orange CountyOsceola CountyWinter ParkCrime and Public Safety