Sylvester is a former award-winning columnist for the St. Louis Post-Dispatch. Prior to that, he published Take Five Magazine for 15 years. After leaving the Post-Dispatch in 2009, Sylvester worked as a consultant and researcher for SmileyBooks, owned by public radio and TV commentator Tavis Smiley on several books including, Brainwashed: Challenging the Myth of Black Inferiority, by Tom Burrell, “Too Important to Fail” by Smiley and “The Rich & the Rest of Us,” written by Smiley and Dr. Cornel West. Sylvester founded the Sweet Potato project in 2012, a program that taught urban youth entrepreneurism through agriculture.
In 2019, Sylvester self-published his own book “When We Listen: Recognizing the Potential of Urban Youth.” Sylvester was awarded the 2020 Deaconess Foundation Fellowship to chronicle the impact of COVID-19 on the lives of Black St. Louisans for the St. Louis American newspaper. His latest book, "White Castles with Jesus & Uncle Ray," a collection of his short stories and commentaries was published in January or 2021.