Overtown Street Fighter Big Red Hustles and Grows

And finds his way from lawless to legit.

A powwow of prostitutes and drug addicts is taking swigs from brown bags under the Metrorail in southeast Overtown when Big Red shows up. Tiny baggies and cigarette butts litter the patch of bleached grass, where the crew sits in lawn chairs, jabbering about the cops. Red, a hulking 52-year-old, hops off his bicycle and joins the party. He steps past Margarita, a boney woman with blood under her fingernails who has nodded off, and stands in front of a guy with missing front teeth. "Move," he rasps.

The toothless man quickly surrenders his plastic chair. Red unzips a small pouch, takes out a hypodermic needle, and stuffs it into his fanny pack. Then he disappears behind an abandoned building — only to resurface a few minutes later with a sack of onion puffs. He sets the chips, along with a container of blue juice, on Margarita's inert lap and smiles. "Can't nobody hustle like me," he says.

Around his waist, Red usually sports an old, leathery weightlifting belt. His hair is short, aside from a tail of matted dreadlocks, and his beard is beginning to gray. A muscular six feet tall, he seems — strikingly — larger.

On the lawless streets of Overtown, Big Red makes the rules. He's a savvy entrepreneur of the ghetto, a hustler with a hardened magnetism who makes folks with nothing want to follow his lead. People call him "a legend" and "King of the Swamp." He's not the kind of guy you'd want to run into in the middle of the night. Over the past 10 years, according to Red, he's been a hit man, drug dealer, and pimp. ("Only thing that made me king is cuz" — he says, pounding a giant fist into his hand as an explanation — "they used to call me Captain Save-a-Ho.") 

While Red has his own set of ethics and loyalties, he's earned street cred through his sense of humor and unflinching ruthlessness. His is the tale of the day-to-day survival of a crafty homeless man, the street economy he negotiates, and the long odds against someone with a criminal past trying to change his ways.

Red's real name is Howard Willard Jenkins. He was born December 29, 1955, in the small town of Richmond, Indiana. His nickname refers to his light skin tone. Although both of his parents are black, the color of his skin is more like a weak glass of Ovaltine.

Red's single mother couldn't afford to take care of him. So she sent him to live with friends in Chicago when he was seven. His adoptive parents — a teacher and the vice president of a life insurance company — changed his name to Howard Heffner. They were middle class but enrolled him at inner-city schools to toughen him up. They knew he would get flack for his skin, he says, and wanted him to face it early on. Back then he was "freckle-faced" and "kinda nerdy."

By sixth grade, he had been kicked out of school five times for fighting. "I wasn't like other kids. I had a knife collection," he says. "I always wanted to protect myself."

After graduating high school, Red dug graves for the Army in South Carolina and worked as a security guard at Chicago nightclubs. He tried working in real estate but was fired after calling a client "a little bitch."

By the end of the Eighties, money was tight, and run-ins with the law started to pile up. In April 1990, he began serving six years at the Ohio State Penitentiary for robbery and aggravated assault on a police officer. The way Red tells it, he was stealing a package of pork chops for a girl he liked. When cops came, he ran and a rookie officer was injured along the way.

In prison, he says, he took classes and earned a bachelor's degree in marketing from Ohio University. He was released in 1996 for good behavior.

The next year, he and a "crackhead" girlfriend drove his Cadillac to Panama City, where he was later charged with battery on three occasions. He was sentenced to a maximum of three months in county jail.

Six months later, he drove to Miami and checked into a cheap motel on Biscayne Boulevard. He'd seen Miami Vice — girls going to the market in their bikinis — and thought it would be the right place to start over. He worked as a janitor for a few years and applied to work for the Miami Heat. But there was "too much going on in the street."

A former lawyer who knew Red from those days — we'll call him Manny — says he thought Red was funny and charismatic, despite the fact that "his clothes were rotting off of him," "he carried around a knife on a stick," and he "traveled with a pack of dogs." At night, Manny would go to Overtown to buy crack, and he paid Red to serve as an unofficial bodyguard.

"He's the most dangerous person I've ever met," Manny, now clean and sober, says. "I think life threw him a curveball and he didn't know how to cope."

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