[4] He is the only son of Jewel Lafontant and John W. Rogers Sr. His mother was the first African American woman to graduate from the University of Chicago Law School in 1946.

His father was a Tuskegee airman pilot with over 100 combat missions of service during World War II and an eventual Cook County judge for twenty years.

Rogers helped finance Before They Die!, a documentary detailing some survivor accounts, and made a brief appearance in the film.

He went to college at Princeton University, where he spent time at his local stock brokerage and where he was influenced by Burton Malkiel's A Random Walk Down Wall Street.

A few years later, and with the financial backing of family and friends, he opened his own firm, starting with the Municipal Employees' Annuity & Benefit Fund of Chicago as his first account.

Rogers is co-chairman of Jesse Jackson's annual Wall Street Project minority conference, chairman of the Chicago Urban League, a member of four corporate boards and was a leading campaigner for Princeton basketball legend and United States Senator Bill Bradley's 2000 United States presidential campaign.

He has served numerous civic, educational and arts organizations as a director or trustee, including the Rainbow/PUSH Coalition, and the Chicago Symphony Orchestra.

[27] In the early 1990s, Rogers served as a fundraising leader in Project Vote efforts led by former United States President Barack Obama.

As a result of his money and time investment 80% of the eighth-grade graduates from the academy are accepted at elite area high schools.

[32] He served along with Bill Daley, Pat Ryan, Penny Pritzker and Julianna Smoot on Barack Obama 2009 presidential inauguration committee.

[33][34] Since late December 2011, the basketball court in the main competition gym at the University of Chicago Laboratory Schools has been named after Rogers.

His name was printed on the floor during Winter Break of the 2011–12 school year, and the court's new title was officially adopted on February 8, 2012, in a ceremony corresponding with Lab's home game against conference rival Northridge Prep.

The result caused spectator and actor Damon Wayans to tell Jordan in front of the campers, “How do you feel about getting humiliated by a man five years older?".