My Brother's Keeper of Greater Richmond

"Encouraging Brothers Through the Storms of Life"

Everything worked out fine until he fractured his ankle and had to go to the hospital. That’s when his employer found out he was not legally old enough to work. “They wanted to keep me, but they couldn’t. They had to let me go.”


After that, Bailey got “caught up in street life.” He had observed the older guys in his neighborhood, watched them in the revolving door of incarceration. “I lost fear of going to prison. I lost fear of dying. . . We in the hood, who’s going to rescue us. We gotta do what we gotta do,” Bailey rationalized at the time. So he dropped out of high school and entered the school of hard knocks. “I always hustled. I always had to do stuff to make ends meet. I was hanging out there late at night, smoking, drinking doing wrong things at the time. I was lost, soul lost, life lost, didn’t care.”


He battled with his mom over his lifestyle. “I knew she loved me, but she used to tell me ‘Jimmy you aint gonna be nothing when you grow up.’” Of course, the words cut deep. Bailey believes that the conflicts between he and his mother stemmed partly from her failed relationships. “When they [men] broke her heart and tore her down she kind of took it out on me.”


However, there was one family member who was always in his corner. “The only person that gave me the love and attention and told me I was going to make it and be successful was my grandmother,” Bailey said. She told him, “As long as you live don’t ever let anybody tell you that you’re not going to make it. You’re special. God brought you here for a reason.”


From his mid-teens, Bailey worked regular jobs while maintaining his street hustle. “Around 18 or 19, I said if I’m going to be a hustler, I’m going to be the best at it.” But when his first son was born, a seed of change began to sprout. “I looked at him and I said I don’t want this for him, but I want this for me so how do I hide this from my kids.”


Bailey described his life as a movie, to which God was giving him a preview. He saw friends being killed, going to jail. A future that could easily have been his except for a chance encounter with a truck driver in the neighborhood, who was the boyfriend of his mother’s friend. The truck driver told him he would teach him how to drive trucks iif the youngster gave up his street life. Bailey took him up on the offer, working 12 hour days for free while not entirely giving up his side hustle. Eventually, he did gain his truck driving license. “As I got into driving, I started seeing more people going to prison, more people dying.” 

He had another son with a woman, he loved and expected to marry. However, that relationship didn’t work out and it left him heartbroken. He prayed, “God if you can just put this woman in my life that can help me be a better person.” Eventually, that prayer was answered when he met his future wife Chandra. The couple has been married for nearly 20 years now. In addition to his wife, Bailey credits his pastor George Williams, with helping him to grow as a Christian and as a man. “When I gave my life to Christ, I felt like somebody just pulled everything up off me. Everything got light. . . I feel so new, I feel washed, I feel covered.”


But making the transition from a street hustler to a man of God didn’t mean Bailey was immune from trouble and heartbreak. He met his only daughter, Jacoby, when she was 14 because her mother had initially said another man was the girl’s father. 


They would only spend seven years together before she died from a blood clot after giving birth to a son. “I got her saved two weeks before she died,” Bailey said. “I told her you’ve got to stay with God.” “I miss her but I can’t be selfish because [God] allowed me to have her and we all belong to Him.”