OKEECHOBEE -- Howard “Sport” Pickering’s great, great grandfather, Henry Hudson Hancock, moved to the east side of Taylor Creek from the Fort Meade area in 1902.

Henry Hancock was appointed justice of the peace and cattle inspector for district 6 of Tantie in 1905. In 1917 Hancock was appointed the first judge of Okeechobee County. Sport’s father, Howard Pickering Sr., was an Okeechobee County sheriff’s deputy and an Okeechobee City police officer between the 1970s and 1980s.



Howard Sr. also had two cousins who were sworn law enforcement officers. Sport has one brother who retired with 35 years of law enforcement experience between Okeechobee County and Martin County. In addition, Sport has another brother and a nephew who are still sworn law enforcement officers at this time.

Before Sport started his career in law enforcement, he made his living as a cowboy, day working for ranches in and around the Okeechobee area and South Florida. Sport started his career in law enforcement in 2006 when he volunteered with the Okeechobee County Sheriff’s Posse and later joined the Sheriff’s Auxiliary.

In 2008 he became a full-time deputy and in 2010, he transferred to the north end Agricultural Division. In 2013 he was promoted to the Criminal Investigations Division (Detective Division) where he remains today.