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The Villages
Thursday, June 2, 2022

Man who stole firetruck in The Villages tries to persuade judge he’s ‘not a flight risk’

Jessie Webb
Jessie Webb

A man who has stolen and taken wild rides in a firetruck and a Community Watch vehicle in The Villages contends he is “not a flight risk.”

In a handwritten letter on file in Sumter County Court, 32-year-old Jessie Charles Webb has pleaded with a judge to set an affordable bond so he can be released from custody.

Webb has been jailed since stealing The Villages Public Safety Department Ford F-550 basic life support vehicle in March while it was on an emergency call.

In the letter, Webb contends he is “not a flight risk,” has “stable housing” and that he is “a resident of Central Florida and has ties to the community.”

Webb has a long criminal history was arrested after holding a woman at knifepoint for several hours on New Year’s Day on the Historic Side of The Villages. She eventually broke free and ran to a gas station pleading for help. Officers arrested Webb in the carport of the St. Andrews Boulevard home where he was living. He had a bloody knife attached to his belt. He was later released from jail on his own recognizance.

This Villages Public Safety Department vehicle was snatched Wednesday afternoon while on an emergency medical call
This Villages Public Safety Department vehicle was snatched in March while on an emergency medical call.

After his release in that case, Webb stole the emergency vehicle and ditched it at the Properties of The Villages Sales Center at Lake Sumter Landing. He was apprehended a short time later near Sonny’s BBQ on Canal Street. Webb had driven the the emergency vehicle, valued at $100,000 and containing $10,000 worth of sensitive medical equipment, over the bridge at Lake Sumter before abandoning it. A helicopter from the Sumter County Sheriff’s Office had joined in the chase which began earlier in the afternoon when Webb stole a bucket truck and then a golf cart in Lady Lake before happening upon The Villages Public Safety Department emergency response vehicle. When Webb jumped into the emergency vehicle, its lights were activated as it was on an emergency call.

Jessie Webb stole and later crashed this Community Watch vehicle in 2019 in The Villages.

Webb was arrested in 2019 after stealing a Community Watch vehicle. He was taken into custody after he crashed that vehicle.

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