Gail Winston

Gail Winston is one busy lady. She’s like the energy bunny that never stops, and that’s because she’s on a mission; a mission to change the lives of people in her community, particularly children. She’s on a mission to restore hope to those who have lost hope and to encourage and minister to those who need guidance and direction. Helping others and making a difference in their lives is the fuel that feeds her frenzy.

Born on the Southside of Chicago, Winston grew up attending Catholic schools. She went on to receive a bachelor’s degree in history from the University of Illinois—Circle Campus.

Winston readily shares that because she lost her father to tuberculosis at a very young age and was raised by her grandmother and extended family, she has more compassion for and capacity to help others who have experienced loss or need help and encouragement.

After marrying, Winston’s husband got a job in Milwaukee, so she moved here and found work as a paraprofessional in Milwaukee Public Schools. Since her degree was in history, with an emphasis on Black History, over the years Winston volunteered to organize and coordinate Black History programs—no matter what school she was employed with. She felt that it was important for students to understand and respect their history.

Winston’s overall goal is to restore the love of God within the family. She works with youth to help them love and respect their bodies. She works with churches of various denominations, trying to unify and encourage them to work together. She works with men to restore the core of the Black family. And, she believes that many in the community have lost faith because many of the larger churches have moved away.

Winston is currently serving her second term on the Board of Directors of the Social Development Commission (SDC) and she is working within her district, along with the third district police department to rid the neighborhood of drugs. She spends an enormous amount of time coaching, mentoring and working with youth and families, trying to empower them.

Winston may be a grandmother of seven, but she’s not about to slow down. There’s too much work to be done in the community and as long as there is, this legend doesn’t have time to sit on her laurels.