Sitting at a table in Oliver’s just down the block from Woodstock Square, eating his go-to lunch of steak tenderloin sliders with onion straws and American cheese, Jack Darby can’t escape his popularity with teenagers.

As soon as a small group of Woodstock High School sophomore student-athletes walks into Oliver’s bar and grill, they spy the broad-shouldered, flannel-shirt-wearing Darby and start chanting. The boys have been dismissed from school early after taking the ACT.

“Dar-by, Dar-by.”

Darby, who turns 80 on May 27 and considers himself a longtime “Blue Streak,” although he graduated from Belvidere High in 1964, immediately sees the boys. They stroll up to him, even before they’re seated.

Small talk ensues. Laughs follow. Darby, always curious, busts the boys’ chops about not being in school and jokes he scored a 37 on his ACT. They play along. No one is better at friendly exchanges than the former college basketball player, real estate agent and freshman study hall supervisor for Woodstock’s Blue Streaks.

Darby still fills in as a substitute teacher once or twice a week.

“For some reason, I just get along with them,” Darby said of the students, boys and girls, at WHS. “And I can tell it to them straight.”

When Jack Darby talks, ears perk. Born with a booming voice – think Radio Hall of Famer and former WGN agriculture and business reporter Orion Samuelson – the charming and quick-witted Darby is a natural speaker. For about the past 15 years, he’s done the public-address announcing for the Woodstock boys and girls home basketball games, although he stopped doing the girls games years ago.

People always compliment him about his deep voice, which drowns out even the loudest crowds in “The Ship,” Woodstock’s James M. Shipley Memorial Gymnasium.

“You know what they add to that, usually?” said Darby, about to unleash his sensational sense of humor. “They say, ‘You got a beautiful radio voice … and a radio face to go along with it."

His chuckle is equally bassy.

“The thing I always appreciated most about him is that he connected with every kid – not just our athletes, but everyone,“ Woodstock athletic director Al Baker said.

Blue Streaks boys basketball coach Ryan Starnes calls Darby one of a kind.

“I think the best way to describe him is that he is just someone you want to be around,” Starnes said. “I tell my players all the time that they should surround themselves with people who bring out the best in you. Jack is that. He is kind, caring and has a great sense of humor.”

Darby married his high school sweetheart, Kay, after they graduated from college. The newlyweds moved to Woodstock in 1968 and rented a second-floor apartment on South Street, just down the street from the high school. Jack attended all of the football and basketball games and later served as an assistant basketball coach.

“I became a Blue Streak a long time ago,” Darby said.

Jack and Kay have two children, Brett and Melissa, and three grandkids. The couple bought a house in 1972 in Todd Woods subdivision by the courthouse off Route 47. In 1989, they moved across the street on Hickory Road and have lived there ever since. His other home for years was a corner office off the Square, Harding Real Estate. Sensing a change in the real estate landscape, he got out in 2005.

In 2007, Darby saw an ad in The Woodstock Independent: “Associate wanted, Woodstock High School.” Darby went to the high school to talk to his good friend Ron Bendis, who was the assistant principal at the time.

“He said, ‘You don’t want any part of this,’” Darby said of Bendis, who died in 2019. “He said, ‘It’s freshman study hall monitor. It’s boring. You’re dealing with immature freshmen.’”

Darby accepted. He monitored freshman study halls for 15 years, befriending hundreds of kids, regardless of their maturity level, while also serving as lunchroom supervisor and in-school suspension supervisor over the years. He easily connected with kids, despite the age gap.

“I still had my teaching certificate, so [the school] loved me because I could fill in for some of the classes when the teacher had to leave early,” Darby said. “I just fell in love with the staff.”

Darby is essentially a member of the boys basketball staff. Since Starnes isn’t in the building at WHS, he relies on Darby all the time. The former 6-foot-2 high school center played two years of college basketball at Iowa Wesleyan, where he was a teammate of future baseball All-Star Davey Lopes.

“He is helpful passing along messages, collecting gear, checking on grades, providing reminders – for the kids who need them – anything and everything,“ Starnes said. ”He is always willing to help. I think that is what makes him so special. He always puts others first. He shows up to practice, supports the fundraiser, takes the varsity boys out to dinner. ... He always wants to help."

Baker said if a kid can’t cover the cost of gear or summer camp, Darby helps out. Darby picks up tabs for team dinners and team-building activities, Baker said.

Darby gets emotional when he talks about his induction into the Blue Streaks Hall of Fame years ago. The many awards he earned for his work in real estate pale in comparison. So, too, does being named Belvidere High’s Most Outstanding Senior Athlete in 1964.

“That was the highlight of my career,” Darby said proudly of the WHS Hall of Fame honor. “I’m just a Blue Streak.”