Born and raised on the West side of Chicago, Sherman began playing softball in the alleys and schoolyards of K-Town. He started playing sixteeninch softball at LaFollette Park with the Pirates, a team of high school buddies. After he graduated from Prosser Vocational High School, he played for the Cougars, Wild Bunch, T. Birds, Devils, Beavers, and Boss Larrys. Sherman played third base and shortstop on teams that won titles at Lafollette Park, Franklin Park, Garfield Park, and Maywood Park. Once he graduated from Lewis University, he was recruited to play with the legendary Safari Tigers. His skills helped them win many league championships. They were also runnersup at the 1984 and 1985 ASA Major Nationals. He played under Claude Rhodes (HOF) and soon was bit by the managerial bug. He was given the opportunity to manage in the spring of 1984 when he became the player / manager for the California Gold. They won league titles at Garfield and Maywood Parks. In 1994 the B-Athletes were created with Sherman as manager. They won many championships at Hamilton, Ogden, and Washington Parks. They were the first team to win the Mike Royko Tournament in Grant Park, with fellow coaches Floyd Glover, and Raymond “Doc” Warren. They also placed fifth in the 1999 ASA Major Nationals. They also played in the Forest Park “No Gloves” Nationals and in the Pro League. In 2004, Sherman was approached by veteran Dogg Pound players to take over the reins of the team. They won titles at Washington Park’s Wednesday and Friday leagues and also clinched The Sunday’s Best titles. In 2006, they won several Claude Rhode Tournaments and placed fourth in the 2006 ASA “A” Nationals at Cedar Rapids, Iowa. In 2009, he coached the Solutions, leading them to titles at Washington Park and to three Southwest Windy City Classic championships (2009, 2010, 2011.) In September 2011 Solutions won the ASA “A” Nationals in Cedar Rapids, Iowa. Sherman and his wonderful wife, Sharon, live in Chicago, Illinois. They have three children – Quintel (Jersan), Jason (Cady), and Sherman, III and two grandchildren, Bella and Jalen. 11