Attempted murder suspect leads Osceola County deputies on chase, gets apprehended in Orange County

Jordan Bailey arrested in Winter Park

WINTER PARK, Fla – An attempted murder suspect led Osceola County deputies on a chase before being taken into custody in Orange County, deputies said.

Footage from the scene Wednesday night showed a large law enforcement presence at Fairbanks Avenue and Clay Street in Winter Park.

According to the Orange County Sheriff’s Office, the Osceola County Sheriff’s Office was involved in a vehicle pursuit of a suspect within its jurisdiction.

A law enforcement presence at Clay Street and Fairbanks Avenue in Winter Park. (Copyright 2025 by WKMG ClickOrlando - All rights reserved.)

As the pursuit continued, the suspect’s vehicle entered Orange County, where deputies assisted in apprehending Jordan Bailey in the 600 block of Clay Street.

Bailey was identified as the suspect in a March 13 shooting on 3307 Pershing Street in Kissimmee, according to police. An arrest warrant was obtained charging Bailey with attempted first-degree murder with a firearm and possession of a firearm by a convicted felon.

Bailey was arrested with the assistance of U.S. Marshals, Osceola County and Orange County deputies, and the Florida Highway Patrol.

Jordan Bailey (Copyright 2025 by WKMG ClickOrlando - All rights reserved.)

[EXCLUSIVE: Become a News 6 Insider (it’s FREE) | PINIT! Share your photos]

Orange County Sheriff's cruiser damaged in Winter Park. (Copyright 2025 by WKMG ClickOrlando - All rights reserved.)

Footage from the scene also showed front-end damage to an Orange County Sheriff’s Office cruiser. According to the sheriff’s office, no deputies were injured.

Rhonda Harmon, who works near the scene, said she heard the chase unfold.

“I work in this building right here. I was sitting upstairs working, and I heard all the sirens,” Harmon said. “Then I heard more and more sirens, so I was like, OK, maybe I should get up. And then I heard a boom. I said, ‘Wait a minute, let me get up.‘”

“Then I saw the guy crawling on his belly,” Harmon recalled. “You know, they had him crawl out on his belly with his hands up.”

The intensity of the response left witnesses on edge.

“It’s a little frightening because, you know, if you had seen all the cop cars. They had a line all the way down the street, helicopters flying. I was like, is this a murderer or somebody that has guns?” Harmon said.

“For them to crash the car into his truck, two of them, to stop him, it must have been something bad,” Harmon added. “He must have done something bad and was involved in something bad.”


About the Authors
Haley Coomes headshot

Haley is a digital content producer for ClickOrlando.com and first started as a News 6 producer in October 2014. She's a graduate of Indiana University with a Bachelors of Arts degree in journalism. She specializes in theme parks and lifestyle writing.

Troy Campbell headshot

Troy graduated from California State University Northridge with a Bachelor's Degree in Communication. He has reported on Mexican drug cartel violence on the El Paso/ Juarez border, nuclear testing facilities at the Idaho National Laboratory and severe Winter weather in Michigan.