Charlie Whitehead was born in Ohio, but raised in Tennessee and Kentucky with three siblings and what he describes as first-class parents. He went to college in Kentucky and South Dakota, playing football and basketball. He never graduated, but says he knows a lot of uneducated folks who did. Charlie worked in the ag business in northern Colorado for a few years – everything from truck-driving to equipment operator to working the pickle docks.
He later lived in Phoenix with his girlfriend Debbie working construction before moving to Fort Myers Beach in 1985 to take a job with then weekly newspaper Beach Bulletin. He married Debbie in 1989 – smartest thing he ever did, he says. Went to work for the Bonita Banner, then the Naples Daily News until the newspaper industry, “started circling the bowl” and his job was eliminated in 2010 when the paper stopped covering Lee County. After, “farting around with freelance and a couple of other publications” he went back into construction full-time. Charlie ran unsuccessfully for a Lee County commission seat in 2010 with no party affiliation. He’s got four grown kids, ranging from 40 to 21. And he’s been umpiring since he a middle teenager, and has been a Little League coach and was a high school softball coach when his daughters were in school. These days he says he’s laying low fixing his Irma-broken house.