A person once approached a dugout at a slow-pitch softball game happening in the area, curious to know how it was going. He asked the nearest man inside the dugout who was winning.

“I’m Winning,” the man replied.

The person outside the dugout was confused. He asked again and received the same response. Emphasizing each of his words for clarity, he asked yet again. He didn’t realize he had just been offered a couple of honest introductions, though the man offering them knew it was information on the game that was desired.

The man inside the dugout was Winning Queensberry, and he was having some good-natured fun. He still recalls his team was behind at the time. It is not in his nature to overlook such a detail.

By now, many people in the Heart of Virginia and beyond would need no introduction to Queensberry. Born in Meherrin in 1954 and a resident of Farmville since 1977, he is well known due to a variety of roles he has filled over the years.

He was a delivery driver for the National Linen Service for 12 years.

“I had a truck, and I had a route,” he said, “and I worked Farmville, Crewe, Buckingham, Powhatan, Cumberland, all stuff down (Route) 45 and Route 60 into Crewe and down (U.S. Route) 360 to Amelia.”

At his stops he would deliver a variety of items, including uniforms, rugs, mops, etc.

He described taking this job as the best decision he has made in his life.

“It was easy to do,” he said. “It kind of put in me in the perspective of meeting a lot of people.”

This was something he said helped shape him as a person.

“I really enjoyed it,” he said.

After this job, he worked as a delivery driver with Green Front Furniture for 19 years.

“I met people from Milwaukee, Wisconsin, to Derry, New Hampshire, to Savannah, Georgia, and if I ever delivered furniture to them, they remembered me,” he said.

Part of it was due to his unusual name, but it was also a result of his engaging, friendly personality and the respect for other people’s time that his father instilled in him from an early age.

Queensberry hurt his knee in 2008 and has retired since then, but he said he has been told by people at Green Front that customers still ask about him.

Something else that has long been a big part of Queensberry’s life is sports, whether he is playing, commentating or watching.

His opportunities to play organized sports in his youth were limited, but he took advantage of them when they were there. He played little league baseball in Meherrin from ages 8-12 before the leagues ended due to lack of children participating. He played for Charlotte County’s all-star youth baseball teams.

“Meherrin is on the tip of Charlotte, Lunenburg and Prince Edward,” he said. “I went to school in Lunenburg, and I played ball in Charlotte County, and I feel like I’m from Prince Edward.”

He went to Central High School of Lunenburg but noted that he lived about 20 miles away, making it hard to get to practice for school sports. He said when he was of age to play high school football, he could have caught a ride from Meherrin to Victoria to play, but his father, Garland Queensberry, wouldn’t allow it.

“He said we were going to get hurt,” Winning said. “I wish I had been able to play. Who knows? I had some size, I could throw a football a mile.”

He said Central’s coach sent a letter to his father, telling him that if he would allow Winning to play, he promised him the starting quarterback position.

Winning did not end up playing organized sports again until he went to try out for the baseball team during his senior year.

In his adult life, he has pursued a variety of sports, including softball and golf. He enjoys these activities because competitiveness is one of his key character traits.

“I mean, my name is Winning, right?” he said. “And yes, I used to throw darts, and I did pretty well with them. And I bowled two years in a bowling league, and I came in second in the first year, and I won it the second year. … And I shoot pool and I play Ping-Pong. If you can do it, I’m going to try it.”

He holds to an uncompromising perspective when it comes to winning.

“I used to tell people, ‘They say, ‘It’s not whether you win or lose, it’s how you play the game.’ I say, ‘But why do they keep score?’ So if I’m playing my grandmother in Ping-Pong, at the end of the game, she better look out,” he said with a laugh. “I’m going to knock one down her throat a hundred miles an hour, if necessary, to win the game.”

When it comes to his unusual first name, he said he did not think anything about it when he was young. It was his grandfather’s name, as well as his.

“I didn’t think much of it, but when you go to school and people say, ‘That’s your name?!’ and I say, ‘Yes, that’s my name,’ and then it got to be the point I was a little adamant about about it, ‘That IS my name, and I’ll show you if you want to try me at anything,’ and it just kind of led me to that path of being, I think, ultra competitive with anything I do,” he said. “I don’t know whether that’s because I’m named Winning.”

Overall, he said he likes the name.

His interest in sports helped him become involved in covering Hampden-Sydney College and high school football games on the radio as a sideline reporter.

“Mr. Cannon Watson got me started with that,” he said. “… It was fun.”

After Watson moved on from broadcasting, Queensberry moved to the broadcast booth and continues to announce high school games on Friday nights.

As a spectator, Queensberry has been a Green Bay Packers fan since 1963, a Boston Red Sox fan since 1967 and a New England Patriots fan since 1971.

Asked to provide three words to describe himself, Queensberry listed competitive, loyal and down-to-earth.

He also enjoys filling some of his free time with musical pursuits, which may be in the genes. A cousin of Roy Clark, musician and host of the television variety show “Hee Haw,” Queensberry is a self-taught guitar player of some 50 years.

He grew up on a farm, the sixth of nine children, and described the secret to happiness as family, good friends and good times.