From car detailing to the National Guard to drumming, it’s safe to say Warren James Flanagan is a jack-of-all-trades. Born on the South Side of Chicago, the 56-year-old has achieved enough to satisfy most people’s needs for a lifetime.
At just 2 years old, Flanagan found his true love: the drums. His father, who was one of the first to play at the legendary Kingston Mines Blues Center, introduced him to the drums and blues at an early age. Flanagan has played at venues including The House of Blues, Buddy Guy’s Legends, and, of course, Kingston Mines.
Despite his older age and surgery to his left wrist, Flanagan continues to hit the snare and the bass with as much vitality as he did 30 years ago. “I absolutely love playing the drums,” Flanagan says. “At night, I’m on stage from 9 p.m. to 3 a.m. Nothing is going to stop me from playing.”
The height of Flanagan’s drumming career came during an unexpected period: during his time with the National Guard. Flanagan joined the National Guard after an army recruiter approached him and his band at a talent show. The recruiter offered to keep Flanagan and his band members together during their time with the National Guard. In their early 20s, the band members saw no reason not to join.
The years spent with the National Guard offered a lot of excitement to Flanagan. “During my time I was a paratrooper jumping out of airplanes,” says Flanagan. Being in the National Guard also came with a lot of responsibility, says Flanagan. “I commanded five to six men at a time and was constantly responsible for their actions. The Guard really taught me about discipline and how to work diligently.”
After his years with the service, Flanagan came back to his native Chicago and worked in a car detailing shop. He worked in the one-car garage near Wrigley Field until he could afford a larger, four-car garage. “I’m a car detailer by trade,” says Flanagan. “One of the reasons why I am selling StreetWise is to get enough money to reopen the garage.” He also mentioned that his ideal setting would be to work in the car-detailing garage and sell StreetWise.
Since he ran out of work at the garage, Warren James Flanagan had homelessly roamed around the streets of Chicago until he found StreetWise. Realizing panhandling was illegal and the streets were too dangerous, Flanagan came to StreetWise’s doorstep looking for employment. Since that day, Flanagan hasn’t looked back.
“It took me two heart attacks and five robberies to realize that I had to get off the street,” says Flanagan. “It was too dangerous for me and people were always trying to take advantage of you.”
StreetWise has had such a profound impact on Flanagan’s life that he can recount his first vending experience like it was yesterday.
“A lady came up to me and gave me $5 for the StreetWise I was selling. I told her that it only cost $2 and she told me to keep the change,” says Flanagan. “She then accidentally dropped another $5 on the ground and told me to keep all $10. I told her I wouldn’t accept it, and she replied by saying that she wouldn’t take back the money because she was Jesus. I then replied, ‘No, you’re not Jesus, but I’m glad He sent you.’”
Written by Sam McGarvey, StreetWise Contributor