An ordinary afternoon in a Windermere subdivision turned ugly when deputies say a local driver hit an 11-year-old on an e-bike with his SUV, then smashed the child's cellphone during a tense street confrontation. The boy managed to move partially out of the vehicle's path but still suffered a leg injury, according to law enforcement accounts.
Officials identified the driver as 44-year-old Gregory Richard Hoole of Windermere. Deputies responded Wednesday afternoon to the area of Golden Dewdrop Trail and Black Rail Street after a reported crash involving a Ford Explorer and an e-bike, according to ClickOrlando. An arrest affidavit reviewed by reporters states the Explorer ran a stop sign, crossed into the opposite lane, and struck the child's e-bike before the driver got out and confronted a group of juveniles.
During that encounter, deputies say Hoole grabbed the 11-year-old's cellphone and shattered it in the street. The child later told officers the driver "smacked" his arm and destroyed the phone, which the family described as an iPhone 15 Pro Mini and estimated, along with other related equipment, to be worth about $700, according to ClickOrlando.
Court calendar shows case on the docket
Orange County public court records list a criminal case filed as State of Florida v. Hoole, Gregory Richard (case no. 2026-CF-009726-A-O), with a jail-court entry scheduled on Thursday. That entry corroborates the arrest and booking and shows the case was logged into the county system shortly after deputies say the incident occurred, according to the Orange County Clerk of Courts.
Neighbor video, parents and the affidavit
The arrest affidavit notes that neighborhood surveillance video captured a dark Ford Explorer rolling through a stop sign at the intersection, then turning into the oncoming lane before striking the e-bike. The child reported that after the impact, the driver confronted the group, "smacked" his arm, and smashed the phone in the roadway. The document also references an earlier dispute tied to a Fourth of July fireworks incident and states that Hoole called 911 to report what he described as a "strong-arm robbery" before he confronted the juveniles, according to ClickOrlando.
Legal implications
The affidavit lists charges against Hoole that include aggravated assault with a motor vehicle, child abuse, and criminal mischief. Under Florida law, aggravated assault is defined and classified as a third-degree felony, and criminal mischief penalties are scaled according to the dollar amount of damage, which can make the offense either a misdemeanor or a felony depending on repair costs. For statutory definitions and penalty ranges, see the Florida Senate, the Florida Senate and the state's official statutes at Online Sunshine.
As of the latest public entries, Hoole had been taken to the Orange County Jail and was being held without bond while the case moved through the local court system. For now, the arrest affidavit and court filings remain the primary public records available, with more details likely to surface as prosecutors formally file charges or the clerk posts additional documents.
