Off-Duty

The city's longest-running sheriff's deputy, Winston Maxey, turns in his keys.


Without training in firearms or first aid, Maxey spent his first four years as deputy transporting inmates between area courthouses and jail with his partner, Edward Grizzard. They were the only two city sergeants charged with the task. The vans they drove had no radios to relay trouble and, likewise, there were no leg irons for prisoners — only handcuffs.

There were no breaks on their watch, but there was a close call.

One morning, back when Judge Moscoe Huntley presided over a second-floor courtroom in Old City Hall, Maxey and Grizzard were escorting inmates in two groups from a van on Broad Street to Huntley’s court. Maxey took the first set. But when he returned to meet his partner, he found mayhem. Uncuffed from lockup, one of the prisoners attempted to flee. When Grizzard tried to stop him, the inmate slashed Maxey’s partner in the back of the neck with razor blades he’d managed to hide. Thanks to Maxey, no prisoners escaped, but Grizzard’s injuries took him out of the job for a year.

Decades have passed since then. And when Maxey looks back on his career, he sees judges and criminals and a courthouse connecting them. And those who know him say his ability to marshal quiet strength and treat everyone with respect made him a model sheriff’s deputy.

In 1955, Maxey graduated from John Marshall High School and found work at a meatpacking plant on Overbrook Road. When the company closed seven years later, Maxey was out of a job, a situation he hasn’t been in since — until now.

Maxey, 69, retired July 7 after 44 years with the Richmond Sheriff’s Department. He’s spent more time at his post as deputy than any person in the department’s history.

His tenure goes back to a time when the city jail was located at Deep Water Terminal on the South Side, not far from where the Philip Morris plant is today. The Richmond sheriff, Frank A. Cavedo, and his deputies were called city sergeants then. (Cavedo’s grandson, Bradley B. Cavedo, is now a Richmond Circuit Court judge.)

Maxey witnessed the construction of the Richmond City Jail on Fairfield Way 41 years ago. Originally, he recalls, 40 or so inmates were kept to a tier; each now holds more than 100. In his time spent as a sheriff’s deputy, the number of inmates has tripled.

Soon after the new jail was built, Maxey was transferred to Manchester Courthouse, where he’s served for 38 years. He meets a reporter on a recent afternoon in a dusty-blue courtroom with blue leather chairs — Maxey points to one he occupied for a decade. The room has an antiquated, small-town feel. Portraits of judges line the walls.

“Each individual has a different situation that brings him to court. And many are mad before they get here,” Maxey says. “But if you can more or less point them in the right direction and treat them with respect, it helps to hold the dam.”

When asked why he’s stayed so long in one place, Maxey simply replies: “It’s had its ups and downs but it’s always been a real pleasure.”

You get a sense he means it. He stands tall and talks quiet, exuding a natural assurance. If he were cast in the movie “The Shawshank Redemption,” he’d be more suited to play Tim Robbins’ character, Andy Dufresne, than an intimidating prison guard.

“He’s very even-tempered but strong physically,” says Patricia Maxey, his wife of 42 years. He took care not to bring his work home. “I know he held things in, wanting to keep a lot of it from me,” she says. Maxey would come home and play with his two daughters and work in the garden. He spent 15 years as a clerk at Ukrop’s — James Ukrop was a classmate and friend of Maxey’s — so he could put his daughters through college.

Richmond Sheriff C.T. Woody says Maxey will be a hard act to follow. The two have known each other for years, back when Woody was a homicide detective with Richmond Police.

“I’ve never seen a situation he couldn’t handle,” Woody says of Maxey’s acuity. What’s more, he adds: “He’s humble and has a heart. He didn’t want to be a captain or a lieutenant or a sheriff, just himself.”

Maxey plans to spend most of his retirement time baby-sitting two granddaughters, ages 5 and 1. What’s left he’ll apply to gardening and volunteering. There’s no place in particular he says he’s dying to see or path he hopes to blaze. As he did with his career, he says he’ll take his new life one day at a time.

“I learned that honesty and treating people with respect will carry you far,” he says. “Maybe that’s why it seems like I’m able to get along so well.” S

  • Click here for more News and Features
  • TRENDING

    WHAT YOU WANT TO KNOW — straight to your inbox

    * indicates required
    Our mailing lists: